[3] 5-('GH')-3-((4-('GH')piperazin-1-yl)methyl)-1H-indole by Asch

Query Query N

Results

Date

181 substances in Reaxys

2017-11-11 00h:15m:26s (EST)

1. Query

Search as: As drawn, No mixtures, No isotopes, No charges, No radicals

1/378

2017-11-11 00:22:14

Reaxys ID 9130285 View in Reaxys

1/181 Chemical Name: N-piperazinyl-3-indolylmethylamine; 3-(4H-piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C13H17N3 Molecular Formula: C13H17N3 Molecular Weight: 215.298 Type of Substance: heterocyclic InChI Key: ZTNAIHGOFCMOPJ-UHFFFAOYSA-N Note:

Substance Label (3) Label References 10

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, Tong-Hua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys

D 156

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

1.285

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

122 - 123

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Medchem (6) 1 of 6

Target Name

Melanocyte-stimulating hormone receptor [human]

Target Synonyms

mc1-r; mc1r; melanocortin receptor 1; melanocyte-stimulating hormone receptor; msh-r; mshr

Target Uniprot ID

q01726

Target, Subunit, Species Melanocyte-stimulating hormone receptor [human] Target Mutant/Chimera Details

Melanocyte-stimulating hormone receptor [human]:Wild

2/378

2017-11-11 00:22:14

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

9130285View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 2 of 6

Target Name

Melanocortin receptor 3 [human]

Target Synonyms

mc3-r; mc3r; melanocortin receptor 3

Target Uniprot ID

p41968

Target, Subunit, Species Melanocortin receptor 3 [human] Target Mutant/Chimera Details

Melanocortin receptor 3 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

9130285View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 3 of 6

Target Name

Melanocortin receptor 4 [human]

Target Synonyms

mc4-r; mc4r; melanocortin receptor 4

Target Uniprot ID

p32245

Target, Subunit, Species Melanocortin receptor 4 [human] Target Mutant/Chimera Details

Melanocortin receptor 4 [human]:Wild

3/378

2017-11-11 00:22:14

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

9130285View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 4 of 6

Target Name

Melanocortin receptor 5 [human]

Target Synonyms

mc-2; mc5-r; mc5r; melanocortin receptor 5

Target Uniprot ID

p33032

Target, Subunit, Species Melanocortin receptor 5 [human] Target Mutant/Chimera Details

Melanocortin receptor 5 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

9130285View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Quantitative value

256

Measurement pX

3.59

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 5 of 6

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

4/378

2017-11-11 00:22:14

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

9130285View in Reaxys

Substance Name

N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

148.07

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

9130285View in Reaxys

Substance Name

N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

65.58

Reaxys ID 885083 View in Reaxys

2/181 CAS Registry Number: 5444-91-7 Chemical Name: 3-[(4-methyl-1-piperazinyl)methyl]-1H-indole; N-methyl-N-piperazinyl-3-indolylmethylamine; 3-(4-methyl-piperazin-1-ylmethyl)-indole; 3-(4-methylpiperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C14H19N3

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Molecular Formula: C14H19N3 Molecular Weight: 229.325 Type of Substance: heterocyclic InChI Key: YLWXBMKGZWALKM-UHFFFAOYSA-N Note: Substance Label (3) Label References 8a

Nirogi, Ramakrishna; Shinde, Anil; Kambhampati, Rama Sastry; Mohammed, Abdul Rasheed; Saraf, Sangram Keshari; Badange, Rajesh kumar; Bandyala, Thrinath Reddy; Bhatta, Venugopalarao; Bojja, Kumar; Reballi, Veena; Subramanian, Ramkumar; Benade, Vijay; Palacharla, Raghava Choudary; Bhyrapuneni, Gopinadh; Jayarajan, Pradeep; Goyal, Vinod; Jasti, Venkat; Journal of Medicinal Chemistry; vol. 60; nb. 5; (2017); p. 1843 - 1859, View in Reaxys

D 151; D 188

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

1.524

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (3) 1 of 3

Melting Point [°C]

137 - 138

Melting Point [°C]

158 - 160

Orth et al.; Journal of Pharmaceutical Sciences; vol. 57; (1968); p. 1814,1815, View in Reaxys 3 of 3

Melting Point [°C]

157 - 160

Patent; Inst. Luso Farmaco; GB1075156; (1963); Chem.Abstr.; vol. 68; nb. 69041k; (1968), View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

6/378

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Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

Comment (Mass Spectrometry)

supporting information

EI (Electron impact); Spectrum

ESI (Electrospray ionisation)

References

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 285 VIS) [nm] Log epsilon

4.4

Target Name

Proto-oncogene tyrosine-protein kinase Src

Target Synonyms

cg7524; dsrc64; neuronal proto-oncogene tyrosine-protein kinase src; p60-src; pp60c-src; proto-oncogene c-src; proto-oncogene tyrosine-protein kinase src; src; src1 (proto-oncogene tyrosine-protein kinase src); src64b; tyrosine-protein kinase src64b

Target, Subunit, Species Proto-oncogene tyrosine-protein kinase Src

7/378

2017-11-11 00:22:14

2 of 4

Target Mutant/Chimera Details

Proto-oncogene tyrosine-protein kinase Src:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

885083View in Reaxys

Substance Name

Substance Dose

7 µM

Measurement Parameter

IC50

Unit

µM

Quantitative value

338.32

Deviation

4.56000

Measurement pX

3.47

Concomitants: Compound RN

73010; 506008

Concomitants: Compound name

ATP; DMSO

Concomitants: Compound role

COE; SLV

Target Name

5-Hydroxytryptamine 6 receptor [human]

Target Synonyms

5-hydroxytryptamine 6 receptor

Target, Subunit, Species 5-Hydroxytryptamine 6 receptor [human] Target Mutant/Chimera Details

5-Hydroxytryptamine 6 receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

885083View in Reaxys

Substance Name

3-[(4-methyl-1-piperazinyl)methyl]-1H-indole

Measurement Parameter

Unit

Quantitative value

482

Measurement pX

6.32

Concomitants: Compound RN

25263076

Concomitants: Compound name

[3H] lysergic acid diethylamide

Concomitants: Compound role

RAD

8/378

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3 of 4

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

885083View in Reaxys

Substance Name

N-methyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

83.26

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

885083View in Reaxys

Substance Name

N-methyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

72.38

9/378

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Reaxys ID 616281 View in Reaxys

3/181 CAS Registry Number: 58433-77-5 Chemical Name: 4-indol-3-ylmethyl-piperazin-1-ylamine; 3-(4aminopiperazin-1-yl)-methylindole; 3-(4-aminopiperazin-1yl)methylindole Linear Structure Formula: C13H18N4 Molecular Formula: C13H18N4 Molecular Weight: 230.313 Type of Substance: heterocyclic InChI Key: WAEYKEUXVHQOSI-UHFFFAOYSA-N Note:

NH 2

Substance Label (2) Label References 7

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys

Patent-Specific Data (1) Location in Patent References Claim

Patent; American Hoechst Corporation; US3997539; (1976); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.076

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.29

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

147 - 149

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys; Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Reaxys ID 6145388 View in Reaxys

4/181 Chemical Name: 5-fluoro-3-<(4-piperazinyl)methyl>-1H-indole Linear Structure Formula: C13H16FN3 Molecular Formula: C13H16FN3 Molecular Weight: 233.289 Type of Substance: heterocyclic InChI Key: PFOFHPUVOGVDPE-UHFFFAOYSA-N Note:

NH F N

Druglikeness (1) 1 of 1

LogP

1.446

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.06

Lipinski Number

Veber Number

10/378

2017-11-11 00:22:14

Reaxys ID 31231723 View in Reaxys

5/181 Chemical Name: N-ethyl-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C15H21N3 Molecular Formula: C15H21N3 Molecular Weight: 243.352 InChI Key: UQSASCFTSPWPHK-UHFFFAOYSA-N Note:

Substance Label (1) Label References 12

Druglikeness (1) 1 of 1

LogP

1.947

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry)

11/378

2017-11-11 00:22:14

electrospray ionisation (ESI); spectrum

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Medchem (2) 1 of 2

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231723View in Reaxys

Substance Name

N-ethyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

106.38

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231723View in Reaxys

Substance Name

N-ethyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

12/378

2017-11-11 00:22:14

Measurement Parameter

Agonistic rate

Unit

Quantitative value

116.12

Reaxys ID 618828 View in Reaxys

6/181 CAS Registry Number: 58433-76-4 Chemical Name: 3-(4-nitroso-piperazin-1-ylmethyl)-indole; 3(4-nitrosopiperazin-1-yl)methylindole Linear Structure Formula: C13H16N4O Molecular Formula: C13H16N4O Molecular Weight: 244.296 Type of Substance: heterocyclic InChI Key: ZQSFMPBEDRJMOD-UHFFFAOYSA-N Note:

N O

Substance Label (2) Label References 4

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Ex 3a

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.415

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

51.7

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

116 - 118

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys; Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Reaxys ID 31558193 View in Reaxys

7/181 Chemical Name: 3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-amine Linear Structure Formula: C14H20N4 Molecular Formula: C14H20N4 Molecular Weight: 244.34 InChI Key: NSARELUBFYUJHP-UHFFFAOYSA-N Note:

H 2N

NH N

Substance Label (2) Label References 3b

13/378

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14e

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.707

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.29

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties brown

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

Reaxys ID 21044275 View in Reaxys

8/181 CAS Registry Number: 1258296-97-7 Linear Structure Formula: C14H18FN3 Molecular Formula: C14H18FN3 Molecular Weight: 247.315 InChI Key: AWTPQMDTRQRTGS-UHFFFAOYSA-N Note:

F NH

Substance Label (1) Label References 8f

Druglikeness (1) 1 of 1

LogP

1.685

14/378

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H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Soubhye, Jalal; Prevost, Martine; Van Antwerpen, Pierre; Zouaoui Boudjeltia, Karim; Rousseau, Alexandre; Furtmueller, Paul G.; Obinger, Christian; Vanhaeverbeek, Michel; Ducobu, Jean; Neve, Jean; Gelbcke, Michel; Dufrasne, Francois; Journal of Medicinal Chemistry; vol. 53; nb. 24; (2010); p. 8747 - 8759, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

19.84

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Soubhye, Jalal; Prevost, Martine; Van Antwerpen, Pierre; Zouaoui Boudjeltia, Karim; Rousseau, Alexandre; Furtmueller, Paul G.; Obinger, Christian; Vanhaeverbeek, Michel; Ducobu, Jean; Neve, Jean; Gelbcke, Michel; Dufrasne, Francois; Journal of Medicinal Chemistry; vol. 53; nb. 24; (2010); p. 8747 - 8759, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

19.84

Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

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Description (Mass Location Spectrometry)

References

HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); TOFMS (Time of flight mass spectrum); Spectrum

supporting information

Medchem (2) 1 of 2

Target Name

Myeloperoxidase

Target Synonyms

mpo; myeloperoxidase; uncleaved myeloperoxidase

Target, Subunit, Species Myeloperoxidase Target Mutant/Chimera Details

Myeloperoxidase:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against oxidation of LDL (1000 ug/ml) by recombinant Myeloperoxidase (1 ug/ml) upon incubation in presence of 100 uM H2O2 for 5 min at 37 degree C in PBS buffer, pH 7.2 by Lowry assay

Substance RN

21044275View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound name

H2O2; LDL

Concomitants: Compound role

COM; COM

Target Name

Myeloperoxidase

Target Synonyms

mpo; myeloperoxidase; uncleaved myeloperoxidase

Target, Subunit, Species Myeloperoxidase Target Mutant/Chimera Details

Myeloperoxidase:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against recombinant Myeloperoxidase upon incubation in presence of 15 mM taurine, 100 uM H2O2 for 5 min at 37 degree C in 10 mM Phosphate buffer, pH 7.4

Substance RN

21044275View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

16/378

2017-11-11 00:22:14

Quantitative value

Deviation

0.1

Measurement pX

Concomitants: Compound name

H2O2; Taurine

Concomitants: Compound role

COM; COM

Reaxys ID 27604335 View in Reaxys

9/181 Chemical Name: 3-{[4-(prop-2-yn-1-yl)piperazine-1-yl]methyl}-1H-indole Linear Structure Formula: C16H19N3 Molecular Formula: C16H19N3 Molecular Weight: 253.347 InChI Key: NWSUXYSNUGRBLB-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 14

Druglikeness (1) 1 of 1

LogP

1.792

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

122

Solvent (Melting Point)

neat (no solvent, solid phase)

Location

supporting information

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5466 - 5469, View in Reaxys Chromatographic Data (1) Chromatographic Location data TLC (Thin layer chromatography)

supporting information

Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5466 - 5469, View in Reaxys References Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5466 - 5469, View in Reaxys

NMR Spectroscopy (2)

17/378

2017-11-11 00:22:14

1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Description (IR Spectroscopy)

ATR (attenuated total reflectance); Intensity of IR bands; Bands

Location

supporting information

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5466 - 5469, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

References

supporting information

Reaxys ID 22705323 View in Reaxys

10/181 CAS Registry Number: 101831-78-1 Chemical Name: 3-((4-methylpiperazin-1-yl)methyl)-1H-indole-5-carbonitrile; 3-[(4-methyl-1-piperazinyl)methyl]-1H-indole-5-carbonitrile Linear Structure Formula: C15H18N4 Molecular Formula: C15H18N4 Molecular Weight: 254.335 InChI Key: PVNWVAMWFWITOQ-UHFFFAOYSA-N Note:

N N

N H

Substance Label (1)

18/378

2017-11-11 00:22:14

Label

References

Mesaik, M. Ahmed; Khan, Khalid Mohammed; Rahim, Fazal; Taha, Muhammad; Haider, Syed Moazzam; Perveen, Shahnaz; Khalid, Ahmed Shukralla; Abdalla, Omer M.; Soomro, Samreen; Voelter, Wolfgang; Bioorganic Chemistry; vol. 60; (2015); p. 118 - 122, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.247

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 280 VIS) [nm] Log epsilon

4.1

Reaxys ID 22848088 View in Reaxys

11/181

19/378

2017-11-11 00:22:14

CAS Registry Number: 1329045-35-3 Chemical Name: 3-[(4-acetylpiperazin-1-yl)methyl]-1H-indole; N-acetyl-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C15H19N3O Molecular Formula: C15H19N3O Molecular Weight: 257.335 InChI Key: UMKHJBUHGGCRGL-UHFFFAOYSA-N Note:

Substance Label (1) Label References 17

Druglikeness (1) 1 of 1

LogP

1.313

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

39.34

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

116 - 116.5

Melting Point [°C]

197.3

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (5) 1 of 5

Substance Effect

Antiproliferative

20/378

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Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848088View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 5

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848088View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 5

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22848088View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 4 of 5

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

22848088View in Reaxys

Substance Name

N-acetyl-N-piperazinyl-3-indolylmethylamine

21/378

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Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

-9.34

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

22848088View in Reaxys

Substance Name

N-acetyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

21.3

Reaxys ID 24294127 View in Reaxys

12/181 Linear Structure Formula: C14H19N5 Molecular Formula: C14H19N5 Molecular Weight: 257.338 InChI Key: JFHFDNKKARCSBD-UHFFFAOYSA-N Note:

N NH

NH 2

Druglikeness (1) 1 of 1

LogP

1.961

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.14

Lipinski Number

22/378

2017-11-11 00:22:14

Veber Number

Medchem (4) 1 of 4

Target Name

Melanocyte-stimulating hormone receptor [human]

Target Synonyms

mc1-r; mc1r; melanocortin receptor 1; melanocyte-stimulating hormone receptor; msh-r; mshr

Target Uniprot ID

q01726

Target, Subunit, Species Melanocyte-stimulating hormone receptor [human] Target Mutant/Chimera Details

Melanocyte-stimulating hormone receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

24294127View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 2 of 4

Target Name

Melanocortin receptor 3 [human]

Target Synonyms

mc3-r; mc3r; melanocortin receptor 3

Target Uniprot ID

p41968

Target, Subunit, Species Melanocortin receptor 3 [human] Target Mutant/Chimera Details

Melanocortin receptor 3 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

24294127View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

23/378

2017-11-11 00:22:14

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 3 of 4

Target Name

Melanocortin receptor 4 [human]

Target Synonyms

mc4-r; mc4r; melanocortin receptor 4

Target Uniprot ID

p32245

Target, Subunit, Species Melanocortin receptor 4 [human] Target Mutant/Chimera Details

Melanocortin receptor 4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

24294127View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys 4 of 4

Target Name

Melanocortin receptor 5 [human]

Target Synonyms

mc-2; mc5-r; mc5r; melanocortin receptor 5

Target Uniprot ID

p33032

Target, Subunit, Species Melanocortin receptor 5 [human] Target Mutant/Chimera Details

Melanocortin receptor 5 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

COS1

Cell Fraction

Membrane

Substance RN

24294127View in Reaxys

Substance Name

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

1000

24/378

2017-11-11 00:22:14

Measurement pX

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys

Reaxys ID 31231726 View in Reaxys

13/181 Chemical Name: N-isopropyl-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C16H23N3 Molecular Formula: C16H23N3 Molecular Weight: 257.379 InChI Key: NARZHCAAZXBIBS-UHFFFAOYSA-N Note:

Substance Label (1) Label References 16

Druglikeness (1) 1 of 1

LogP

2.407

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

118 - 119

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy)

25/378

2017-11-11 00:22:14

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Medchem (2) 1 of 2

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231726View in Reaxys

Substance Name

N-isopropyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

127.11

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

26/378

2017-11-11 00:22:14

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231726View in Reaxys

Substance Name

N-isopropyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

243.78

Reaxys ID 31231725 View in Reaxys

14/181 Chemical Name: N-aminoethyl-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C15H22N4 Molecular Formula: C15H22N4 Molecular Weight: 258.366 InChI Key: JPWDEEQWKASEET-UHFFFAOYSA-N Note:

NH 2

Substance Label (1) Label References 15

Druglikeness (1) 1 of 1

LogP

0.748

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.29

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy)

27/378

2017-11-11 00:22:14

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Medchem (2) 1 of 2

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231725View in Reaxys

Substance Name

N-aminoethyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

110.08

28/378

2017-11-11 00:22:14

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231725View in Reaxys

Substance Name

N-aminoethyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

166.6

Reaxys ID 805970 View in Reaxys

15/181 CAS Registry Number: 17511-49-8 Chemical Name: N-(2″-hydroxyethyl)-N-piperazinyl-3-indolylmethylamine; 2-(4-indol-3-ylmethyl-piperazin-1-yl)-ethanol Linear Structure Formula: C15H21N3O Molecular Formula: C15H21N3O Molecular Weight: 259.351 Type of Substance: heterocyclic InChI Key: FLOIUBOBDOJASU-UHFFFAOYSA-N Note:

N OH

Substance Label (1) Label References 13

Druglikeness (1) 1 of 1

LogP

0.815

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

42.5

29/378

2017-11-11 00:22:14

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

86 - 87

Melting Point [°C]

85 - 95

Patent; Inst. Luso Farmaco; GB1075156; (1963); Chem.Abstr.; vol. 68; nb. 69041k; (1968), View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Medchem (2) 1 of 2

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

805970View in Reaxys

Substance Name

N-(2″-hydroxyethyl)-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

49.52

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

30/378

2017-11-11 00:22:14

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

805970View in Reaxys

Substance Name

N-(2″-hydroxyethyl)-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

56.94

Reaxys ID 11950927 View in Reaxys

16/181 CAS Registry Number: 701205-15-4 Chemical Name: 5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1H-indole; 5-methoxy-3-(4-methylpiperazin-1-ylmethyl)-1Hindole; 5-Methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1H-indole Linear Structure Formula: C15H21N3O Molecular Formula: C15H21N3O Molecular Weight: 259.351 InChI Key: LBQPYBWHUQEKBA-UHFFFAOYSA-N Note:

O NH

Substance Label (3) Label References 8h

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; WO2015/83179; (2015); (A1) English, View in Reaxys; Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys

D 154

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

1.439

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Melting Point (3) 1 of 3

Melting Point [°C]

139 - 140.6

31/378

2017-11-11 00:22:14

Melting Point [°C]

139 - 140.6

Location

Paragraph 0033

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys 3 of 3

Melting Point [°C]

139 - 140.6

Solvent (Melting Point)

toluene

Location

Page/Page column 9

References

white

Paragraph 0026

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys

white

Page/Page column 8

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; WO2015/83179; (2015); (A1) English, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy)

32/378

2017-11-11 00:22:14

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

10035] ‘H-NMR (CDC13, ö ppm): 2.30 (3H, s), 2.5 (8H,bs), 3.71 (2H, s), 3.86 (3H, s), 6.83-6.86 (iH, dd, J=8.8i, 2.7Hz), 7.01 (iH, d, J=2.06 Hz), 7.18-7.20 (2H, m), 8.91 (iH,s);

Location

Paragraph 0035

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

10036] ‘3C-NMR (CDC13, ö ppm): 45.89, 52.79, 53.39,55.11, 55.83, 101.3, 111.39, 111.75, 111.81, 124.88, 128.45,131.48, 153.77;

Location

Paragraph 0036

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys 5 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Location

Page/Page column 9

- NMR (CDCl3, δ ppm): 2.30 (3H, s), 2.5 (8H, bs), 3.71 (2H, s), 3.86 (3H, s), 6.83 - 6.86 (1H, dd, J = 8.81, 2.71 Hz), 7.01 (1H, d, J = 2.06 Hz), 7.18 - 7.20 (2H, m), 8.91 (1H, s)

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; WO2015/83179; (2015); (A1) English, View in Reaxys 6 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

13C

Location

Page/Page column 9

- NMR (CDCl3, δ ppm): 45.89, 52.79, 53.39, 55.11, 55.83, 101.3, 111.39, 111.75, 111.81, 124.88, 128.45, 131.48, 153.77

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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Description (IR Spectroscopy)

Bands

Original Text (IR Spectroscopy)

IR spectra (cm’): 3125, 2951, 1875, 1622, 1585,1492, 1351, 1288, 1215, 1059, 930, 654;

Location

Paragraph 0034

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Original Text (IR Spectroscopy)

IR spectra (cm-1): 3125, 2951, 1875, 1622, 1585, 1492, 1351, 1288, 1215, 1059, 930, 654

Location

Page/Page column 9

Comment (Mass Spectrometry)

electrospray ionisation (ESI); spectrum

References Nirogi, Ramakrishna; Shinde, Anil; Kambhampati, Rama Sastry; Mohammed, Abdul Rasheed; Saraf, Sangram Keshari; Badange, Rajesh kumar; Bandyala, Thrinath Reddy; Bhatta, Venugopalarao; Bojja, Kumar; Reballi, Veena; Subramanian, Ramkumar; Benade, Vijay; Palacharla, Raghava Choudary; Bhyrapuneni, Gopinadh; Jayarajan, Pradeep; Goyal, Vinod; Jasti, Venkat; Journal of Medicinal Chemistry; vol. 60; nb. 5; (2017); p. 1843 - 1859, View in Reaxys

spectrum

Paragraph 0037

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (7 pag.); US2016/297759; (2016); (A1) English, View in Reaxys

spectrum

Page/Page column 9

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Rama Sastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; WO2015/83179; (2015); (A1) English, View in Reaxys

ESI (Electrospray ionisation)

Molecular peak

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Reaxys ID 11950929 View in Reaxys

17/181 CAS Registry Number: 701205-14-3 Chemical Name: 5-chloro-3-(4-methylpiperazin-1-ylmethyl)-1Hindole Linear Structure Formula: C14H18ClN3 Molecular Formula: C14H18ClN3 Molecular Weight: 263.77 InChI Key: GIMOMCJNROQVGI-UHFFFAOYSA-N Note:

Cl NH

Substance Label (2) Label References 8c

D 153

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References

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Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.146

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 22705325 View in Reaxys

18/181 Chemical Name: 3-[(4-ethyl-1-piperazinyl)methyl]-5-methoxy-1H-indole Linear Structure Formula: C16H23N3O Molecular Formula: C16H23N3O Molecular Weight: 273.378 InChI Key: BRYRTQCGHXJGHS-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 8q

Druglikeness (1) 1 of 1

LogP

1.862

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

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IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 290 VIS) [nm] Log epsilon

4.5

Reaxys ID 31231724 View in Reaxys

19/181 Chemical Name: N-(2″-methoxyethyl)-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C16H23N3O Molecular Formula: C16H23N3O Molecular Weight: 273.378 InChI Key: XMJDUTQRNGWTMC-UHFFFAOYSA-N Note:

Substance Label (1) Label References 14

Druglikeness (1) 1 of 1

LogP

1.334

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2)

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1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Medchem (2) 1 of 2

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231724View in Reaxys

Substance Name

N-(2″-methoxyethyl)-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

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2017-11-11 00:22:14

Quantitative value

68.99

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231724View in Reaxys

Substance Name

N-(2″-methoxyethyl)-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

63.84

Reaxys ID 1592954 View in Reaxys

20/181 CAS Registry Number: 3414-71-9 Chemical Name: 3-((4-methylpiperazin-1-yl)methyl)-5-nitro-1Hindole; 3-(4-methyl-piperazin-1-ylmethyl)-5-nitro-indole; 5-nitro-3-(4-methylpiperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C14H18N4O2 Molecular Formula: C14H18N4O2 Molecular Weight: 274.323 Type of Substance: heterocyclic InChI Key: VGUWZCUCNQXGBU-UHFFFAOYSA-N Note:

NH O

N O

Substance Label (4) Label References 8l

38/378

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13e

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

D 155; D 189

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

1.416

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.09

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

92 - 94

Solvent (Melting Point)

toluene

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys 2 of 2

Melting Point [°C]

92 - 94

Solvent (Melting Point)

ethanol

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum ESI (Electrospray ionisation)

References Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

Molecular peak

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Medchem (1) 1 of 1

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal dose was determined in mice upon intravenous administration

Biological Species/NCBI Mus musculus ID Substance RN

1592954View in Reaxys

Substance Route of Adm.

intravenous administration

Measurement Parameter

LD50

Unit

mg/kg

Qualitative value

Quantitative value

56.2

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DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys

Reaxys ID 30912983 View in Reaxys

21/181 Linear Structure Formula: C15H21N3S Molecular Formula: C15H21N3S Molecular Weight: 275.418 InChI Key: UYKIBHJMUZMXNT-UHFFFAOYSA-N Note:

N S NH

Substance Label (1) Label References 8m

Druglikeness (1) 1 of 1

LogP

2.266

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

47.57

Lipinski Number

Veber Number

Reaxys ID 22705326 View in Reaxys

22/181 Chemical Name: 3-((4-acetylpiperazin-1-yl)methyl)-1H-indole-5-carbonitrile; 3-[(4-acetyl-1-piperazinyl)methyl]-1H-indole-5-carbonitrile Linear Structure Formula: C16H18N4O Molecular Formula: C16H18N4O Molecular Weight: 282.345 InChI Key: QLHMZJMDKGISAT-UHFFFAOYSA-N Note:

N N

N O

N H

Substance Label (1) Label References 8

Druglikeness (1) 1 of 1

LogP

1.036

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.13

Lipinski Number

Veber Number

NMR Spectroscopy (1)

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1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 285 VIS) [nm] Log epsilon

4.4

Reaxys ID 10274924 View in Reaxys

23/181 CAS Registry Number: 887477-38-5 Chemical Name: methyl 3-((4-methylpiperazin-1-yl)methyl)-1Hindole-5-carboxylate Linear Structure Formula: C16H21N3O2 Molecular Formula: C16H21N3O2 Molecular Weight: 287.362 Type of Substance: heterocyclic InChI Key: CEZSEVWPLODBQG-UHFFFAOYSA-N Note:

NH O O

Substance Label (1) Label References 5

Lindquist, Charlotta; Ersoy, Oguz; Somfai, Peter; Tetrahedron; vol. 62; nb. 14; (2006); p. 3439 - 3445, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.46

H Bond Donors

H Bond Acceptors

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Rotatable Bonds

TPSA

48.57

Lipinski Number

Veber Number

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Lindquist, Charlotta; Ersoy, Oguz; Somfai, Peter; Tetrahedron; vol. 62; nb. 14; (2006); p. 3439 - 3445, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lindquist, Charlotta; Ersoy, Oguz; Somfai, Peter; Tetrahedron; vol. 62; nb. 14; (2006); p. 3439 - 3445, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lindquist, Charlotta; Ersoy, Oguz; Somfai, Peter; Tetrahedron; vol. 62; nb. 14; (2006); p. 3439 - 3445, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Lindquist, Charlotta; Ersoy, Oguz; Somfai, Peter; Tetrahedron; vol. 62; nb. 14; (2006); p. 3439 - 3445, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Lindquist, Charlotta; Ersoy, Oguz; Somfai, Peter; Tetrahedron; vol. 62; nb. 14; (2006); p. 3439 - 3445, View in Reaxys

Reaxys ID 25354053 View in Reaxys

24/181

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Linear Structure Formula: C16H21N3O2 Molecular Formula: C16H21N3O2 Molecular Weight: 287.362 InChI Key: IWSHHUVABSTWOO-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

1.907

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.57

Lipinski Number

Veber Number

Medchem (1) 1 of 1

Target Name

Sodium-dependent dopamine transporter [Rattus norvegicus]

Target Synonyms

da transporter; dat; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3

Target Uniprot ID

p23977

Target, Subunit, Species Sodium-dependent dopamine transporter [Rattus norvegicus] Target Mutant/Chimera Details

Sodium-dependent dopamine transporter [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity to dopamine transporter from rat striatal tissue using [3H]WIN 35428 (1.5 nM) as a radioligand at the concentration of 1uM upon preincubation for 5 min with HEPES buffer at pH 7.4

Biological Species/NCBI Rattus norvegicus ID Substance RN

25354053View in Reaxys

Measurement Parameter

Binding Score

Unit

Measurement Object

Specific binding

Qualitative value

Quantitative value

88.53

Concomitants: Compound name

[3H]WIN 35428

Concomitants: Compound role

RAD

Reaxys ID 30912980 View in Reaxys

25/181

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Linear Structure Formula: C17H25N3O Molecular Formula: C17H25N3O Molecular Weight: 287.405 InChI Key: ZFDIFKWMGRIFIG-UHFFFAOYSA-N Note:

N O NH

Substance Label (1) Label References 8i

Druglikeness (1) 1 of 1

LogP

2.322

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Reaxys ID 891857 View in Reaxys

26/181 CAS Registry Number: 4281-72-5 Chemical Name: 3-((4-phenylpiperazin-1-yl)methyl)-1H-indole; 3-[(4-phenyl-1-piperazinyl)methyl]-1H-indole; 3-[(4-phenylpiperazin-1-yl)methyl]-1H-indole; 3-(4-phenylpiperazin-1-ylmethyl)-1H-indole; 3-(4-phenyl-piperazin-1-ylmethyl)-indole Linear Structure Formula: C19H21N3 Molecular Formula: C19H21N3 Molecular Weight: 291.396 Type of Substance: heterocyclic InChI Key: FDOZNCJWYJMHAG-UHFFFAOYSA-N Note:

Substance Label (4) Label References 1

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Kulagowski, Janusz J.; Broughton, Howard B.; Curtis, Neil R.; Mawer, Ian M.; Ridgill, Mark P.; Baker, Raymond; Emms, Frances; Freedman, Stephen B.; Marwood, Rosemarie; Patel, Shil; Patel, Smita; Ragan, C. Ian; Leeson, Paul D.; Journal of Medicinal Chemistry; vol. 39; nb. 10; (1996); p. 1941 - 1942, View in Reaxys

Patent; Sterling Drug Inc.; GB944443; (1959); Chem.Abstr.; vol. 60; nb. 9293g; (1964), View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.812

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

44/378

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Lipinski Number

Veber Number

Melting Point (4) 1 of 4

Melting Point [°C]

179.7

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 4

Melting Point [°C]

185 - 189

Solvent (Melting Point)

ethanol

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 3 of 4

Melting Point [°C]

184.6 - 186.8

Patent; Sterling Drug Inc.; GB944443; (1959); Chem.Abstr.; vol. 60; nb. 9293g; (1964), View in Reaxys; Patent; Sterling Drug Inc.; US3135794; (1964); Chem.Abstr.; vol. 61; nb. 4374g; (1964), View in Reaxys 4 of 4

Melting Point [°C]

183 - 185

Patent; Inst. Luso Farmaco; GB1075156; (1963); Chem.Abstr.; vol. 68; nb. 69041k; (1968), View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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View in Reaxys; Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

spectrum; electron impact (EI)

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 283 VIS) [nm] Log epsilon

4.2

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Substance RN

891857View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

120

Measurement pX

6.92

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

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Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Substance RN

891857View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

280

Measurement pX

6.55

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Substance RN

891857View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

Measurement pX

8.1

Concomitants: Compound RN

632204

47/378

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Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

891857View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

3100

Measurement pX

5.51

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 5 of 25

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

48/378

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Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

891857View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

570

Measurement pX

6.24

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 6 of 25

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

891857View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

660

Measurement pX

6.18

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 7 of 25

Target Name

D(3) dopamine receptor [human]

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Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

891857View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

3400

Measurement pX

5.47

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 8 of 25

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

891857View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

50/378

2017-11-11 00:22:14

Unit

Quantitative value

2.9

Measurement pX

8.54

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 9 of 25

Substance Effect

Toxic : Acute

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

Substance Name

15187

Substance Route of Adm.

intraperitoneal administration

Measurement Parameter

LD50

Unit

mg/kg

Quantitative value

983

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 10 of 25

Substance Effect

Antibiotic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : Mycobacterium tuberculosis H37RvBioassay : reference comp. rifampicin (0.125 μg/ml): 98 percent inhib. bacterium and title comp. incubated in BACTEC 12B medium; broth microdilution assay; Microplate Alamar Blue Assay; antimycobacterial activity determined

Substance RN

891857View in Reaxys

Substance Name

15187

Substance Dose

6.25000 mg/L

Qualitative Results

11 percent inhib.

Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 11 of 25

Substance Effect

Analgesic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : phenylbenzoquinone-induced writhing test

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

51/378

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Substance Name

15187

Substance Dose

12.3000 mg/kg

Qualitative Results

exhibited peripheral analgesic action

Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 12 of 25

Substance Effect

Analgesic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : hot plate test; central analgesia evaluated

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

Substance Name

15187

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 13 of 25

Substance Effect

Anxiolytic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : barbituric-induced sleep observed

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

Substance Name

15187

Substance Dose

24.6000 mg/kg

Qualitative Results

increased sleeping time

Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 14 of 25

Substance Effect

Anxiolytic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : spontaneous locomotor activity observed for 1 h

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

Substance Name

15187

Substance Dose

24.6000 mg/kg

Qualitative Results

suppressed spontaneous locomotor activity during 1 h

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Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 15 of 25

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity towards human dopamine receptor D4 was measured

Biological Species/NCBI Human ID

16 of 25

Substance RN

891857View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

Measurement pX

8.1

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity of compound towards human dopamine receptor D4 over dopamine receptor D2 was measured

Biological Species/NCBI Human ID

17 of 25

Substance RN

891857View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Sodium channel protein type 9 subunit alpha [Rattus norvegicus];+Sodium channel subunit beta-1 [Rattus norvegicus]

Target Synonyms

peripheral sodium channel 1; pn1; scn9a (sodium channel protein type 9 subunit alpha); sodium channel protein type 9 subunit alpha; sodium channel protein type ix subunit alpha; voltage-gated sodium channel subunit alpha nav1.7 + scn1b; sodium channel subunit beta-1

Target Uniprot ID

o08562 + q00954

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Target, Subunit, Species Sodium channel protein type 9 subunit alpha [Rattus norvegicus]; Sodium channel subunit beta-1 [Rattus norvegicus] Target Mutant/Chimera Details

Sodium channel protein type 9 subunit alpha [Rattus norvegicus]:Wild + Sodium channel subunit beta-1 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against Sodium channel of rat cortical membrane using [3H]-batrachotoxin at 1 uM compound concentration

Biological Species/NCBI Rattus norvegicus ID

18 of 25

Substance RN

891857View in Reaxys

Substance Dose

= 1 µm

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound name

[3H]Batrachotoxin

Concomitants: Compound role

RAD

Target Name

Dopamine D4 receptor

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target, Subunit, Species Dopamine D4 receptor

19 of 25

Target Mutant/Chimera Details

Dopamine D4 receptor:Wild

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity of the compound towards Dopamine receptor D4 was determined

Substance RN

891857View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

2.9

Measurement pX

8.54

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Inhibition of head withdrawal reflex when given po in mice

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

Substance Route of Adm.

oral administration

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Measurement Parameter

ED50

Unit

mg/kg

Measurement Object

Head withdrawal reflex

Qualitative value

Quantitative value

128

DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys 20 of 25

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Minimum effective dose causing taming in monkey when given po

Biological Species/NCBI Monkey ID Substance RN

891857View in Reaxys

Substance Route of Adm.

oral administration

Measurement Parameter

MED

Unit

mg/kg

Qualitative value

Quantitative value

DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys 21 of 25

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Minimum effective dose causing sedation in monkey when given po

Biological Species/NCBI Monkey ID Substance RN

891857View in Reaxys

Substance Route of Adm.

oral administration

Measurement Parameter

MED

Unit

mg/kg

Qualitative value

Quantitative value

DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys 22 of 25

Substance Action on Target

Blocker

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Adrenergic blocking activity was evaluated when given iv to rat

Biological Species/NCBI Rattus norvegicus ID Substance RN

891857View in Reaxys

Substance Route of Adm.

intravenous administration

Measurement Parameter

ED50

Unit

µg/kg

Qualitative value

Quantitative value

800

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DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys 23 of 25

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Potentiation of hexobarbital (40 mg/kg) induced anaesthesia (no. of mice losing righting reflex) when given po

Biological Species/NCBI Mus musculus ID Substance RN

891857View in Reaxys

Substance Route of Adm.

oral administration

Measurement Parameter

ED50

Unit

mg/kg

Measurement Object

Potentiation of hexobarbital (40 mg/kg) induced anaesthesia

Qualitative value

Quantitative value

128

DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys 24 of 25

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Fall in rectal temp. was evaluated in monkey when administered (Dose, po)

Biological Species/NCBI Monkey ID Substance RN

891857View in Reaxys

Measurement Parameter

T°

Unit

°C

Quantitative value

DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys 25 of 25

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Minimum effective dose causing catalepsy in monkey when given po

Biological Species/NCBI Monkey ID Substance RN

891857View in Reaxys

Substance Route of Adm.

oral administration

Measurement Parameter

MED

Unit

mg/kg

Qualitative value

Quantitative value

DAVID W. WYLIE; S. ARCHER; Journal of medicinal chemistry; vol. 5; nb. 5; (1962); p. 932 - 943, View in Reaxys

Reaxys ID 11950976 View in Reaxys

27/181

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CAS Registry Number: 300803-90-1 Chemical Name: 3-(4-(pyridin-2-yl)piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C18H20N4 Molecular Formula: C18H20N4 Molecular Weight: 292.384 InChI Key: DGRLQDVYINGXQV-UHFFFAOYSA-N Note:

Substance Label (1) Label References D 160

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.288

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

35.16

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 9714364 View in Reaxys

28/181 Chemical Name: 3-{[4-(pyrimidin-2-yl)piperazin-1-yl]methyl}-1H-indole; 3-[4-(2-pyrimidinyl)-piperazin-1-ylmethyl]-1H-indole Linear Structure Formula: C17H19N5 Molecular Formula: C17H19N5 Molecular Weight: 293.371 Type of Substance: heterocyclic InChI Key: GKKBEFXMNBECNL-UHFFFAOYSA-N Note:

N N N

Substance Label (1) Label References 2g

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.247

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.05

Lipinski Number

Veber Number

Melting Point (2)

57/378

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1 of 2

Melting Point [°C]

200

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 2

Melting Point [°C]

202 - 204

Solvent (Melting Point)

ethyl acetate

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (1) 1 of 1

Substance Effect

Antibiotic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

9714364View in Reaxys

Substance Name

58/378

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Substance Dose

6.25000 mg/L

Qualitative Results

8 percent inhib.

Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys

Reaxys ID 825069 View in Reaxys

29/181 CAS Registry Number: 17511-51-2 Chemical Name: 1-acetoxy-2-(4-indol-3-ylmethyl-piperazin-1yl)-ethane Linear Structure Formula: C17H23N3O2 Molecular Formula: C17H23N3O2 Molecular Weight: 301.389 Type of Substance: heterocyclic InChI Key: SGVVVFMPLMXOMY-UHFFFAOYSA-N Note:

N O O

Druglikeness (1) 1 of 1

LogP

1.555

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.57

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

84 - 88

Patent; Inst. Luso Farmaco; GB1075156; (1963); Chem.Abstr.; vol. 68; nb. 69041k; (1968), View in Reaxys

Reaxys ID 823750 View in Reaxys

30/181 CAS Registry Number: 17511-50-1 Chemical Name: 3-(4-benzyl-piperazin-1-ylmethyl)-indole Linear Structure Formula: C20H23N3 Molecular Formula: C20H23N3 Molecular Weight: 305.423 Type of Substance: heterocyclic InChI Key: YHZKIEWEQQRAHY-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

3.234

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1)

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1 of 1

Melting Point [°C]

160 - 163

Patent; Inst. Luso Farmaco; GB1075156; (1963); Chem.Abstr.; vol. 68; nb. 69041k; (1968), View in Reaxys

Reaxys ID 22848089 View in Reaxys

31/181 CAS Registry Number: 414879-27-9 Chemical Name: 3-{[4-(2-methylphenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H23N3 Molecular Formula: C20H23N3 Molecular Weight: 305.423 InChI Key: YQZHTUZDSCIWGT-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

4.038

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

89.9

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848089View in Reaxys

Measurement Parameter

IC50

60/378

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Unit

µM

Quantitative value

8.48

Measurement pX

5.07

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848089View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

13.37

Measurement pX

4.87

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22848089View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

7.14

Measurement pX

5.15

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 22848090 View in Reaxys

32/181 CAS Registry Number: 1403574-74-2 Chemical Name: 3-{[4-(4-methylphenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H23N3 Molecular Formula: C20H23N3 Molecular Weight: 305.423 InChI Key: BCJGEKQHRKDXCR-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

4.249

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

61/378

2017-11-11 00:22:14

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

168.2

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848090View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848090View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

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Substance RN

22848090View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 11950923 View in Reaxys

33/181 CAS Registry Number: 701205-13-2 Chemical Name: 5-bromo-3-(4-methylpiperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C14H18BrN3 Molecular Formula: C14H18BrN3 Molecular Weight: 308.221 InChI Key: HWXULFBLEGVJDK-UHFFFAOYSA-N Note:

N Br NH

Substance Label (2) Label References 8e

D 152

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.322

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 22705329 View in Reaxys

34/181 CAS Registry Number: 383149-20-0 Chemical Name: (4-((1H-indol-3-yl)methyl)piperazin-1-yl)(furan-2-yl)methanone; 2-furyl[4-(1H-indol-3-ylmethyl)-1-piperazinyl]methanone Linear Structure Formula: C18H19N3O2 Molecular Formula: C18H19N3O2

O N

N H

N O

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Molecular Weight: 309.368 InChI Key: HZDVQZKEWSXXOR-UHFFFAOYSA-N Note: Substance Label (1) Label References 9

Druglikeness (1) 1 of 1

LogP

1.73

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

52.48

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 282 VIS) [nm] Log epsilon

4.2

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Reaxys ID 895145 View in Reaxys

35/181 CAS Registry Number: 20094-55-7 Chemical Name: 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-1H-indole; 3-[4-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-indole; 3-<4-(4-Fluorphenyl)-1-piperazinylmethyl)indol; 3-<4-(4Fluorphenyl)piperazinomethyl)indol; HTS 06141 Linear Structure Formula: C19H20FN3 Molecular Formula: C19H20FN3 Molecular Weight: 309.386 Type of Substance: heterocyclic InChI Key: PCLWAFVRAWUFRN-UHFFFAOYSA-N Note:

N F

Patent-Specific Data (1) References Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.973

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (3) 1 of 3

Melting Point [°C]

166.8

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Melting Point [°C]

166.8

Solvent (Melting Point)

ethanol; water

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 3 of 3

Melting Point [°C]

164

Patent; Centre Europeen de Recherches Mauvernay; GB1116196; (1966); Chem.Abstr.; vol. 69; nb. 87017g; (1968), View in Reaxys; Patent; Mauvernay; Busch; US3453366; (1966); Chem.Abstr.; vol. 71; nb. 70636b; (1969), View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys; Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy)

65/378

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Nucleus (NMR Spectroscopy)

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys; Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (7) 1 of 7

Target Name

Transient receptor potential cation channel subfamily M member 7 [Mus musculus]

Target Synonyms

chak; channel-kinase 1; long transient receptor potential channel 7; ltrpc-7; ltrpc7; transient receptor potential cation channel subfamily m member 7; transient receptor potentialphospholipase c-interacting kinase; trp-plik; trpm7

Target Uniprot ID

q923j1

Target PDB ID

1ia9; 1iah; 1iaj

Target, Subunit, Species Transient receptor potential cation channel subfamily M member 7 [Mus musculus] Target Mutant/Chimera Details

Transient receptor potential cation channel subfamily M member 7 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Target Transfection

Transfected

Substance Action on Target

Blocker

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

T-REx 293

Substance RN

895145View in Reaxys

Substance Name

114

Substance Dose

39 nM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

7.78

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Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys 2 of 7

Target Name

Opioid Receptor, Sigma 2 [Rattus norvegicus]

Target Synonyms

opioid receptor, sigma 2

Target, Subunit, Species Opioid Receptor, Sigma 2 [Rattus norvegicus] Target Mutant/Chimera Details

Opioid Receptor, Sigma 2 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding affinity of the compound towards rat liver cells Sigma 2 receptor upon incubation in 50 mM TRIS, pH 8 using 3 nM [3H]DITOLYLGUANIDINE as radioligand in presence of 500 nM (+)-PENTAZOCINE at RT for 180 mins

Biological Species/NCBI Rattus norvegicus ID Substance RN

895145View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

660

Measurement pX

6.18

Concomitants: Compound name

(+)-PENTAZOCINE; [3H]DITOLYLGUANIDINE

Concomitants: Compound role

COM; RAD

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 3 of 7

Target Name

Sigma non-opioid intracellular receptor 1 [guinea pig]

Target Synonyms

sigma non-opioid intracellular receptor 1

Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig] Target Mutant/Chimera Details

Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding affinity of the compound towards GUINEA PIG brain cells Sigma 1 receptor upon incubation in 50 mM TRIS, pH 7.4 using 2 nM (+)-[3H]PENTAZOCINE as radioligand at 37 Degree C for 180 mins

Biological Species/NCBI guinea pig ID Cells/Cell Lines

Brain cell

Substance RN

895145View in Reaxys

Measurement Parameter

Unit

67/378

2017-11-11 00:22:14

Qualitative value

Quantitative value

3640

Measurement pX

5.44

Concomitants: Compound name

(+)-[3H]PENTAZOCINE

Concomitants: Compound role

RAD

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 4 of 7

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration of the compound (dissolved in DMSO) against human colon carcinoma HCT 116 cells upon incubation at 37 Degree C for 72 h measured as cell viability using SULFORHODAMINE B (SRB) METHOD

Cells/Cell Lines

HCT116

Substance RN

895145View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

9.32

Measurement pX

5.03

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 5 of 7

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

895145View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

14.63

Measurement pX

4.84

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 6 of 7

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

895145View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

11.65

68/378

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Measurement pX

4.93

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 7 of 7

Target Name

Sigma non-opioid intracellular receptor 1 [guinea pig]

Target Synonyms

sigma non-opioid intracellular receptor 1

Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig] Target Mutant/Chimera Details

Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity is the ratio of binding affinity of the compound towards GUINEA PIG brain cells Sigma 1 receptor to that of RAT liver cells Sigma 2 receptor

Biological Species/NCBI guinea pig ID Cells/Cell Lines

Brain cell

Substance RN

895145View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys

Reaxys ID 22848092 View in Reaxys

36/181 CAS Registry Number: 414886-17-2 Chemical Name: 3-{[4-(2-fluorophenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C19H20FN3 Molecular Formula: C19H20FN3 Molecular Weight: 309.386 InChI Key: CKNQLJYCQLEECC-UHFFFAOYSA-N Note:

N F

Druglikeness (1) 1 of 1

LogP

3.973

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

164.6

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1)

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1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848092View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

6.38

Measurement pX

5.2

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848092View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

8.5

Measurement pX

5.07

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22848092View in Reaxys

Measurement Parameter

IC50

70/378

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Unit

µM

Quantitative value

10.72

Measurement pX

4.97

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 30912989 View in Reaxys

37/181 Chemical Name: N-tert-butyloxycarbonyl-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C18H25N3O2 Molecular Formula: C18H25N3O2 Molecular Weight: 315.415 InChI Key: AUYCPBVTVLXBOP-UHFFFAOYSA-N Note:

O N

Substance Label (2) Label References 8r

Druglikeness (1) 1 of 1

LogP

2.784

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.57

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

160 - 161

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

71/378

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Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Medchem (2) 1 of 2

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

30912989View in Reaxys

Substance Name

N-tert-butyloxycarbonyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

-2.44

Target Name

5-hydroxytryptamine receptor 1a [human]

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Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

30912989View in Reaxys

Substance Name

N-tert-butyloxycarbonyl-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

17.98

Reaxys ID 8788757 View in Reaxys

38/181 Chemical Name: 3-((4-phenylpiperazin-1-yl)methyl)-1H-indole-5-carbonitrile; 3-[(4-phenyl-1-piperazinyl)methyl]-1H-indole-5-carbonitrile Linear Structure Formula: C20H20N4 Molecular Formula: C20H20N4 Molecular Weight: 316.406 Type of Substance: heterocyclic InChI Key: VHPASGHENHNLAW-UHFFFAOYSA-N Note:

Substance Label (2) Label References 2

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.535

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

73/378

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Melting Point (1) 1 of 1

Melting Point [°C]

212

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Description (IR Spectroscopy)

Bands

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1)

74/378

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1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 281 VIS) [nm] Log epsilon

4.1

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

8788757View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

3000

Deviation

750

Measurement pX

5.52

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 6

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

75/378

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Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8788757View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

34000

Deviation

6000

Measurement pX

4.47

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 3 of 6

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8788757View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

3500

Deviation

950

Measurement pX

5.46

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

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Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 4 of 6

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8788757View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

4400

Deviation

1200

Measurement pX

5.36

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 5 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

77/378

2017-11-11 00:22:14

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8788757View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

Deviation

3.50000

Measurement pX

7.3

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 6 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8788757View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Quantitative value

0.9

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

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2017-11-11 00:22:14

Reaxys ID 22848094 View in Reaxys

39/181 CAS Registry Number: 1403574-75-3 Chemical Name: 3-{[4-(2-cyanophenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H20N4 Molecular Formula: C20H20N4 Molecular Weight: 316.406 InChI Key: NJGIWDIZAGDKTQ-UHFFFAOYSA-N Note:

N NH

Druglikeness (1) 1 of 1

LogP

3.535

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

121.9

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848094View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

12.31

Measurement pX

4.91

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

79/378

2017-11-11 00:22:14

2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848094View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

19.48

Measurement pX

4.71

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22848094View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

12.25

Measurement pX

4.91

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 22705330 View in Reaxys

40/181 Chemical Name: ethyl 4-((5-methoxy-1H-indol-3-yl)methyl)piperazine-1-carboxylate; ethyl 4-[(5-methoxy-1H-indol-3-yl)methyl]-1-piperazinecarboxylate Linear Structure Formula: C17H23N3O3 Molecular Formula: C17H23N3O3 Molecular Weight: 317.388 InChI Key: HBYFKBGXGNUEIV-UHFFFAOYSA-N Note:

N O

N H

Substance Label (1) Label References 13

Druglikeness (1) 1 of 1

LogP

1.822

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

57.8

Lipinski Number

Veber Number

80/378

2017-11-11 00:22:14

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 280 VIS) [nm] Log epsilon

4.1

Reaxys ID 22848093 View in Reaxys

41/181 CAS Registry Number: 353772-99-3 Chemical Name: 3-[(4-benzoylpiperazin-1-yl)methyl]-1H-indole Linear Structure Formula: C20H21N3O Molecular Formula: C20H21N3O Molecular Weight: 319.406 InChI Key: IUSKODVEAJAQAA-UHFFFAOYSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

3.03

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

39.34

Lipinski Number

81/378

2017-11-11 00:22:14

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

159.2

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848093View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848093View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

82/378

2017-11-11 00:22:14

Substance RN

22848093View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 9720921 View in Reaxys

42/181 Chemical Name: 3-{[4-(2,3-dimethylphenyl)piperazin-1yl]methyl}-1H-indole; 3-[4-(2,3-dimethylphenyl)-piperazin-1-ylmethyl]-1H-indole Linear Structure Formula: C21H25N3 Molecular Formula: C21H25N3 Molecular Weight: 319.45 Type of Substance: heterocyclic InChI Key: WPTJQRPJBCUVFJ-UHFFFAOYSA-N Note:

Substance Label (1) Label References 2f

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.475

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

173.8

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 2

Melting Point [°C]

169 - 171

Solvent (Melting Point)

ethanol

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (NMR Spec- Chemical shifts troscopy)

83/378

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (2) 1 of 2

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Target : Mycobacterium tuberculosis H37RvBioassay : MIC: lowest conc. effecting reduction in fluorescence of 90 percent relative to control; reference comp. rifampicin (0.125 μg/ ml): 98 percent inhib. bacterium and title comp. incubated in BACTEC 12B medium; broth microdilution assay; Microplate Alamar Blue Assay; antimycobacterial activity determined

Substance RN

9720921View in Reaxys

Substance Name

Substance Dose

6.25000 mg/L

Measurement Parameter

MIC

Unit

mg/L

Quantitative value

6.25

Measurement pX

4.71

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 2 of 2

Substance Effect

Cytotoxic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Bioassay : MTT: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide; selectivity index (SI): IC50/MIC; SI value of < 10 indicates significant cytotoxicity cells incubated with title comp. for 72 h; viability assessed on basis of cellular conversion of MTT into formazan product using Promega CellTiter 96 Non-radioactive Cell Proliferation Assay

Cells/Cell Lines

Vero

Substance RN

9720921View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

mg/L

Quantitative value

Measurement pX

4.73

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys

84/378

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Reaxys ID 1594683 View in Reaxys

43/181 CAS Registry Number: 3414-78-6 Chemical Name: 3-(4-benzyl-piperazin-1-ylmethyl)-indol-5-ylamine Linear Structure Formula: C20H24N4 Molecular Formula: C20H24N4 Molecular Weight: 320.437 Type of Substance: heterocyclic InChI Key: FOXCFIPZINDAQU-UHFFFAOYSA-N Note:

NH H 2N N

Druglikeness (1) 1 of 1

LogP

2.417

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.29

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

147 - 149

Solvent (Melting Point)

benzene; cyclohexane

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys Medchem (1) 1 of 1

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal dose was determined in mice upon intravenous administration

Biological Species/NCBI Mus musculus ID Substance RN

1594683View in Reaxys

Substance Route of Adm.

intravenous administration

Measurement Parameter

LD50

Unit

mg/kg

Qualitative value

Quantitative value

56.2

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys

Reaxys ID 28456677 View in Reaxys

44/181 Chemical Name: 2-(4-((5-chloro-1H-indol-3-yl)methyl)piperazin-1-yl)-N,N-dimethylethan-1-amine Linear Structure Formula: C17H25ClN4 Molecular Formula: C17H25ClN4 Molecular Weight: 320.865 InChI Key: MIXDYGNDLHIDQK-UHFFFAOYSA-N Note:

HN Cl N

Druglikeness (1) 1 of 1

LogP

1.999

H Bond Donors

85/378

2017-11-11 00:22:14

H Bond Acceptors

Rotatable Bonds

TPSA

25.51

Lipinski Number

Veber Number

Reaxys ID 9717898 View in Reaxys

45/181 Chemical Name: 3-[4-(o-methoxyphenyl)-piperazin-1-ylmethyl]-1H-indole; 3-(4-(1-methoxyphen-2-yl)piperazin-1-ylmethyl)-1H-indole; HTS 04868 Linear Structure Formula: C20H23N3O Molecular Formula: C20H23N3O Molecular Weight: 321.422 Type of Substance: heterocyclic InChI Key: OJUQWLAXOIFADL-UHFFFAOYSA-N Note:

NH O N

Substance Label (2) Label References 2b

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

D 157

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (2) References Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.727

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

133 - 135

Solvent (Melting Point)

cyclohexane

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

86/378

2017-11-11 00:22:14

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Medchem (3) 1 of 3

Target Name

Transient receptor potential cation channel subfamily M member 7 [Mus musculus]

Target Synonyms

Target Uniprot ID

q923j1

Target PDB ID

1ia9; 1iah; 1iaj

Target, Subunit, Species Transient receptor potential cation channel subfamily M member 7 [Mus musculus] Target Mutant/Chimera Details

Transient receptor potential cation channel subfamily M member 7 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Target Transfection

Transfected

Substance Action on Target

Blocker

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

T-REx 293

Substance RN

9717898View in Reaxys

Substance Name

Substance Dose

39 nM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

7.78

Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys 2 of 3

Substance Effect

Antibiotic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

9717898View in Reaxys

Substance Name

1286337

Substance Dose

6.25000 mg/L

Qualitative Results

7 percent inhib.

Measurement Parameter

Qualitative

87/378

2017-11-11 00:22:14

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 3 of 3

Target Name

5-hydroxytryptamine receptor 1A [Rattus norvegicus]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; 5ht1a; htr1a; serotonin receptor 1a

Target Uniprot ID

p19327

Target, Subunit, Species 5-hydroxytryptamine receptor 1A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity of the compound towards 5-hydroxytryptamine 1A receptor using [3H]-8OH-DPAT as radioligand in front cortex of rat

Biological Species/NCBI Rattus norvegicus ID Substance RN

9717898View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[3H]8-OH-DPAT

Concomitants: Compound role

RAD

Reaxys ID 22705328 View in Reaxys

46/181

CAS Registry Number: 864389-09-3 Chemical Name: 3-((4-(4-methoxyphenyl)piperazin-1-yl)methyl)-1H-indole; 3-{[4-(4-methoxyphenyl)-1-piperazinyl]methyl}-1H-indole; 3-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H23N3O Molecular Formula: C20H23N3O Molecular Weight: 321.422 InChI Key: CRJJXHKBVLJRSW-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 11

Druglikeness (1) 1 of 1

LogP

3.727

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

88/378

2017-11-11 00:22:14

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

157.2

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys; Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 282 VIS) [nm] Log epsilon

4.2

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

89/378

2017-11-11 00:22:14

Cells/Cell Lines

HCT 116

Substance RN

22705328View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

17.48

Measurement pX

4.76

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22705328View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

18.51

Measurement pX

4.73

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22705328View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

16.48

Measurement pX

4.78

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 22848091 View in Reaxys

47/181 CAS Registry Number: 1403574-73-1 Chemical Name: 3-{[4-(3-methoxyphenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H23N3O Molecular Formula: C20H23N3O Molecular Weight: 321.422 InChI Key: OHTKFJKZUCVOHW-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

3.727

H Bond Donors

90/378

2017-11-11 00:22:14

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

129.2

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848091View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

10.06

Measurement pX

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848091View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

10.01

91/378

2017-11-11 00:22:14

Measurement pX

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22848091View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

10.44

Measurement pX

4.98

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 22705324 View in Reaxys

48/181 Chemical Name: 5-bromo-3-((4-ethylpiperazin-1-yl)methyl)-1Hindole; 5-bromo-3-[(4-ethyl-1-piperazinyl)methyl]-1H-indole Linear Structure Formula: C15H20BrN3 Molecular Formula: C15H20BrN3 Molecular Weight: 322.248 InChI Key: BCECHAQMJIAGTH-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 4

Druglikeness (1) 1 of 1

LogP

2.745

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

92/378

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1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 285 VIS) [nm] Log epsilon

4.4

Reaxys ID 11951037 View in Reaxys

49/181

CAS Registry Number: 701205-19-8 Chemical Name: 5-methoxy-3-(4-(pyridin-2-yl)piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C19H22N4O Molecular Formula: C19H22N4O Molecular Weight: 322.41 InChI Key: PDOAZUDGOPEDOO-UHFFFAOYSA-N Note:

O NH

Substance Label (1) Label References D 162

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.203

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

44.39

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

93/378

2017-11-11 00:22:14

Reaxys ID 7543323 View in Reaxys

50/181 Chemical Name: 3-{[4-(4-chlorophenyl)piperazin-1-yl]methyl}-1H-indole; 3-[4-(4-chlorophenyl)piperazin-1-yl]methylindole Linear Structure Formula: C19H20ClN3 Molecular Formula: C19H20ClN3 Molecular Weight: 325.841 Type of Substance: heterocyclic InChI Key: NRWWWLAGZMNIDV-UHFFFAOYSA-N Note:

N Cl

Substance Label (2) Label References 2a

Loeber, Stefan; Huebner, Harald; Gmeiner, Peter; Bioorganic & Medicinal Chemistry Letters; vol. 9; nb. 1; (1999); p. 97 - 102, View in Reaxys

Showell, Graham A.; Emms, Frances; Marwood, Rosemarie; O'Connor, Desmond; Patel, Smita; Leeson, Paul D.; Bioorganic and Medicinal Chemistry; vol. 6; nb. 1; (1998); p. 1 - 8, View in Reaxys

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 7

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.434

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

174.3

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (13) 1 of 13

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

94/378

2017-11-11 00:22:14

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID

2 of 13

Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

330

Measurement pX

6.48

Concomitants: Compound RN

3620147

Concomitants: Compound name

[3H]-SCH 23390

Concomitants: Compound role

RAD

Target Name

Dopamine 2 long receptor [taurine cattle]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [taurine cattle] Target Mutant/Chimera Details

Dopamine 2 long receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

270

Measurement pX

6.57

95/378

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3 of 13

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human]

4 of 13

Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

430

Measurement pX

6.37

Concomitants: Compound RN

494008; 10134220; 114512; 8172987

Concomitants: Compound name

[3H]-Sulpiride; Gpp(NH)p; 8-Hydroxyquinoline; (-)-Sulpiride

Concomitants: Compound role

RAD; COM; COM; NSB

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

96/378

2017-11-11 00:22:14

5 of 13

Measurement Parameter

Unit

Quantitative value

1.1

Measurement pX

8.96

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

Measurement pX

7.15

Concomitants: Compound RN

632204; 29319

Concomitants: Compound name

[3H]-Spiperone; (-)-Apomorphine

Concomitants: Compound role

RAD; NSB

Showell, Graham A.; Emms, Frances; Marwood, Rosemarie; O'Connor, Desmond; Patel, Smita; Leeson, Paul D.; Bioorganic and Medicinal Chemistry; vol. 6; nb. 1; (1998); p. 1 - 8, View in Reaxys 6 of 13

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

97/378

2017-11-11 00:22:14

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

150

Measurement pX

6.82

Concomitants: Compound RN

632204; 29319

Concomitants: Compound name

[3H]-Spiperone; (-)-Apomorphine

Concomitants: Compound role

RAD; NSB

Showell, Graham A.; Emms, Frances; Marwood, Rosemarie; O'Connor, Desmond; Patel, Smita; Leeson, Paul D.; Bioorganic and Medicinal Chemistry; vol. 6; nb. 1; (1998); p. 1 - 8, View in Reaxys 7 of 13

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

1.6

Measurement pX

8.8

Concomitants: Compound RN

632204; 29319

Concomitants: Compound name

[3H]-Spiperone; (-)-Apomorphine

Concomitants: Compound role

RAD; NSB

Showell, Graham A.; Emms, Frances; Marwood, Rosemarie; O'Connor, Desmond; Patel, Smita; Leeson, Paul D.; Bioorganic and Medicinal Chemistry; vol. 6; nb. 1; (1998); p. 1 - 8, View in Reaxys

98/378

2017-11-11 00:22:14

8 of 13

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

Measurement pX

7.15

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

150

Measurement pX

6.82

99/378

2017-11-11 00:22:14

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Substance RN

7543323View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

1.6

Measurement pX

8.8

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

D(2) dopamine receptor [human]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p14416; p14416-1; p14416-2

Target PDB ID

5aer

Target, Subunit, Species D(2) dopamine receptor [human] Target Mutant/Chimera Details

D(2) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

100/378

2017-11-11 00:22:14

Bioassay Details

In vitro binding affinity towards human dopamine D2 (long) receptor expressed in HEK 293 cells using [125I]IABN as radioligand after incubation with 50 mM Tris-HCl buffer, pH 7.5 for 60 min at 37 degree C

Biological Species/NCBI Human ID

12 of 13

Cells/Cell Lines

HEK 293

Substance RN

7543323View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

Measurement pX

7.15

Concomitants: Compound name

[125I]IABN

Concomitants: Compound role

RAD

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding affinity towards human dopamine D4.4 receptor expressed in HEK 293 cells using [125I]IABN as radioligand after incubation with 50 mM Tris-HCl buffer, pH 7.5 for 60 min at 37 degree C

Biological Species/NCBI Human ID

13 of 13

Cells/Cell Lines

HEK 293

Substance RN

7543323View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

1.6

Measurement pX

8.8

Concomitants: Compound name

[125I]IABN

Concomitants: Compound role

RAD

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

101/378

2017-11-11 00:22:14

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding affinity towards human dopamine D3 receptor expressed in HEK 293 cells using [125I]IABN as radioligand after incubation with 50 mM Tris-HCl buffer, pH 7.5 for 60 min at 37 degree C

Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

7543323View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

150

Measurement pX

6.82

Concomitants: Compound name

[125I]IABN

Concomitants: Compound role

RAD

Reaxys ID 9718412 View in Reaxys

51/181 Chemical Name: 3-{[4-(3-chlorophenyl)piperazin-1-yl]methyl}-1H-indole; 3-[4-(m-chlorophenyl)-piperazin-1-ylmethyl]-1Hindole Linear Structure Formula: C19H20ClN3 Molecular Formula: C19H20ClN3 Molecular Weight: 325.841 Type of Substance: heterocyclic InChI Key: WQILKYINSSRSAR-UHFFFAOYSA-N Note:

Cl N

Substance Label (1) Label References 2d

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.434

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

102/378

2017-11-11 00:22:14

Melting Point (2) 1 of 2

Melting Point [°C]

120.7

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 2

Melting Point [°C]

114 - 116

Solvent (Melting Point)

cyclohexane

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

9718412View in Reaxys

Measurement Parameter

IC50

103/378

2017-11-11 00:22:14

Unit

µM

Quantitative value

7.73

Measurement pX

5.11

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

9718412View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

6.14

Measurement pX

5.21

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

9718412View in Reaxys

Measurement Parameter

IC50

Unit

µM

Quantitative value

9.31

Measurement pX

5.03

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 9718517 View in Reaxys

52/181 Chemical Name: 3-{[4-(2-chlorophenyl)piperazin-1-yl]methyl}-1H-indole; 3-[4-(o-chlorophenyl)-piperazin-1-ylmethyl]-1H-indole Linear Structure Formula: C19H20ClN3 Molecular Formula: C19H20ClN3 Molecular Weight: 325.841 Type of Substance: heterocyclic InChI Key: CMZLSJOICXCPRS-UHFFFAOYSA-N Note:

NH Cl N

Substance Label (1) Label References 2c

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.434

H Bond Donors

104/378

2017-11-11 00:22:14

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

139.5

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 2

Melting Point [°C]

143 - 145

Solvent (Melting Point)

cyclohexane

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

105/378

2017-11-11 00:22:14

Medchem (1) 1 of 1

Substance Effect

Antibiotic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

9718517View in Reaxys

Substance Name

Substance Dose

6.25000 mg/L

Qualitative Results

89 percent inhib.

Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys

Reaxys ID 841199 View in Reaxys

53/181 CAS Registry Number: 34933-60-3 Chemical Name: 1-[(4-indol-3-ylmethyl-piperazin-1-yl)-acetyl]pyrrolidine; 1-(Indol-3-ylmethyl)-4-<(1-pyrrolidinyl-carbonyl)methyl>-piperazin Linear Structure Formula: C19H26N4O Molecular Formula: C19H26N4O Molecular Weight: 326.442 Type of Substance: heterocyclic InChI Key: NZMLXAWUARKVPT-UHFFFAOYSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

1.344

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

42.58

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

192

Patent; Delalande; DE2128520; Chem.Abstr.; vol. 76; nb. 72554a; (1972), View in Reaxys

Reaxys ID 30912981 View in Reaxys

54/181 Linear Structure Formula: C16H20F3N3O Molecular Formula: C16H20F3N3O Molecular Weight: 327.35 InChI Key: ODDYQUQEULJVME-UHFFFAOYSA-N Note:

O NH

Substance Label (1)

106/378

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Label

References

Druglikeness (1) 1 of 1

LogP

2.864

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Reaxys ID 9719223 View in Reaxys

55/181 Chemical Name: 3-(4-cinnamylpiperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C22H25N3 Molecular Formula: C22H25N3 Molecular Weight: 331.461 Type of Substance: heterocyclic InChI Key: IGNXYLSQDZTEII-UHFFFAOYSA-N Note:

Substance Label (1) Label References 2h

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.836

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

156 - 158

Solvent (Melting Point)

cyclohexane

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys Medchem (1) 1 of 1

Substance Effect

Antibiotic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

9719223View in Reaxys

Substance Name

Substance Dose

6.25000 mg/L

Qualitative Results

17 percent inhib.

Measurement Parameter

Qualitative

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys

Reaxys ID 568236 View in Reaxys

56/181 CAS Registry Number: 17740-70-4 Chemical Name: 1-[3-(4-phenyl-piperazin-1-ylmethyl)-indol-5yl]-ethanone Linear Structure Formula: C21H23N3O Molecular Formula: C21H23N3O Molecular Weight: 333.433 Type of Substance: heterocyclic InChI Key: ZIQZINPFRFQMHE-UHFFFAOYSA-N Note:

NH O N

Druglikeness (1) 1 of 1

LogP

3.689

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

39.34

Lipinski Number

Veber Number

108/378

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Melting Point (1) 1 of 1

Melting Point [°C]

169 - 174.2

Patent; Sterling Drug Inc.; US3328407; (1966); Chem.Abstr.; vol. 68; nb. 49652, View in Reaxys

Reaxys ID 22705333 View in Reaxys

57/181 Chemical Name: 3-((4-(furan-2-carbonyl)piperazin-1-yl)methyl)-1H-indole-5-carbonitrile; 3-{[4-(2-furoyl)-1-piperazinyl]methyl}-1H-indole-5-carbonitrile Linear Structure Formula: C19H18N4O2 Molecular Formula: C19H18N4O2 Molecular Weight: 334.378 InChI Key: UTOOYLPWUKZMGS-UHFFFAOYSA-N Note:

N N

N O

N H

Substance Label (1) Label References 6

Druglikeness (1) 1 of 1

LogP

1.453

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

76.27

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 282 VIS) [nm] Log epsilon

4.4

Reaxys ID 8793130 View in Reaxys

58/181 Linear Structure Formula: C20H19N4F Molecular Formula: C20H19FN4 Molecular Weight: 334.396 Type of Substance: heterocyclic InChI Key: WSJMJBOZYZWDIK-UHFFFAOYSA-N Note:

N F

Substance Label (1) Label References 3e

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.696

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

179

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

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Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys Medchem (6) 1 of 6

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

8793130View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

490

Deviation

Measurement pX

6.31

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 6

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

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Substance RN

8793130View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

2400

Deviation

150

Measurement pX

5.62

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 3 of 6

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793130View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

1800

Deviation

Measurement pX

5.74

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 4 of 6

Target Name

D(3) dopamine receptor [human]

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Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793130View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

5200

Deviation

250

Measurement pX

5.28

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 5 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793130View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

113/378

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Measurement Parameter

Unit

Quantitative value

110

Deviation

Measurement pX

6.96

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 6 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793130View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Quantitative value

0.9

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Reaxys ID 626554 View in Reaxys

59/181

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CAS Registry Number: 58434-18-7 Chemical Name: N-(4-indol-3-ylmethyl-piperazin-1-yl)-benzamide Linear Structure Formula: C20H22N4O Molecular Formula: C20H22N4O Molecular Weight: 334.421 Type of Substance: heterocyclic InChI Key: HBJTWTRJRLCVMM-UHFFFAOYSA-N Note:

NH O

Substance Label (2) Label References 32

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Ex. 42

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.669

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

51.37

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

176 - 179

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys 2 of 2

Melting Point [°C]

176 - 178

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys Medchem (2) 1 of 2

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Antihypertensive activity was tested using spontaneous hypertensive rat by a standard indirect tail cuff method on day 1 at oral dose of 100 mg/kg, +/- is marginal or transient activity

Biological Species/NCBI Rattus norvegicus ID Substance RN

626554View in Reaxys

Substance Route of Adm.

oral administration

Qualitative Results

Marginal or transient activity

Glamkowski; Reitano; Woodward; Journal of Medicinal Chemistry; vol. 20; nb. 11; (1977); p. 1485 - 1489, View in Reaxys 2 of 2

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Antihypertensive activity was tested using spontaneous hypertensive rat by a standard indirect tail cuff method on day 3 at oral dose of 100 mg/kg, +/- is marginal or transient activity

Biological Species/NCBI Rattus norvegicus ID Substance RN

626554View in Reaxys

Substance Route of Adm.

oral administration

Qualitative Results

Marginal or transient activity

Glamkowski; Reitano; Woodward; Journal of Medicinal Chemistry; vol. 20; nb. 11; (1977); p. 1485 - 1489, View in Reaxys

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Reaxys ID 11725005 View in Reaxys

60/181 Chemical Name: 3-[4-(3-dimethylaminophenyl)piperazin-1yl]methylindole Linear Structure Formula: C21H26N4 Molecular Formula: C21H26N4 Molecular Weight: 334.464 InChI Key: SCMROHOCVMNFAC-UHFFFAOYSA-N Note:

N N NH N

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 8

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.021

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

25.51

Lipinski Number

Veber Number

Reaxys ID 24363549 View in Reaxys

61/181 Linear Structure Formula: C20H21N3O2 Molecular Formula: C20H21N3O2 Molecular Weight: 335.406 InChI Key: ZGHMWJXLYLNOOG-UHFFFAOYSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

3.301

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.73

Lipinski Number

Veber Number

Medchem (1) 1 of 1

Target Name

Transient receptor potential cation channel subfamily M member 7 [Mus musculus]

Target Synonyms

Target Uniprot ID

q923j1

Target PDB ID

1ia9; 1iah; 1iaj

Target, Subunit, Species Transient receptor potential cation channel subfamily M member 7 [Mus musculus] Target Mutant/Chimera Details

Transient receptor potential cation channel subfamily M member 7 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

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Target Transfection

Transfected

Substance Action on Target

Blocker

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

T-REx 293

Substance RN

24363549View in Reaxys

Substance Name

115

Substance Dose

39 nM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

7.59

Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys

Reaxys ID 19916687 View in Reaxys

62/181 CAS Registry Number: 414882-56-7 Chemical Name: 3-{[4-(2-ethoxyphenyl)-piperazin-1-yl]methyl}-1H-indole; 3-((4-(2-ethoxyphenyl)piperazin-1-yl)methyl)-1Hindole Linear Structure Formula: C21H25N3O Molecular Formula: C21H25N3O Molecular Weight: 335.449 InChI Key: PFALMGBZVKYODL-UHFFFAOYSA-N Note:

N N NH O

Substance Label (2) Label References 14a

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Laboratorios Del. Dr. Esteve, S.A.; EP2149373; (2010); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.15

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

52 - 54

Location

supporting information

117/378

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Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Location

supporting information

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) gas chromatogra- supporting inforphy mass specmation trometry (GCMS); spectrum Use (21) Use Pattern

Location

References Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys

References

5-hydroxytryptaPage/Page colmine receptor umn 9 subtype 7 (serotonin subtype 7, 5HT7) agonist

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

5-HT7 mediated disease

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Pain

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Sleep disorder

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Shift worker syndrome

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

jet lag

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Depression

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Seasonal affective disorder

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Migraine

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Anxiety

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Psychosis

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Schizophrenia

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Cognition disorders

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

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Memory disorders Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Neuronal degeneration resulting from ischemic events

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Cardiovascular disease

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Hypertension

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Irritable bowel syndrome

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Inflammatory bowel disease

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Spastic colon

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

urinary incontinence

Page/Page column 9

Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; US2011/124657; (2011); (A1) English, View in Reaxys

Medchem (10) 1 of 10

Target Name

5-hydroxytryptamine receptor 7 [human]

Target Synonyms

5-ht-7; 5-ht-x; 5-ht7; 5-hydroxytryptamine receptor 7; htr7; serotonin receptor 7

Target Uniprot ID

p34969; p34969-1; p34969-2; p34969-3

Target, Subunit, Species 5-hydroxytryptamine receptor 7 [human]

2 of 10

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 7 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

Substance Dose

1.00000E-05 M

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

5.37

Concomitants: Compound RN

764984; 94179

Concomitants: Compound name

Clozapine; [3H]-LSD; BSA

Concomitants: Compound role

NSB; RAD; COM

Target Name

5-hydroxytryptamine receptor 7 [human]

Target Synonyms

5-ht-7; 5-ht-x; 5-ht7; 5-hydroxytryptamine receptor 7; htr7; serotonin receptor 7

Target Uniprot ID

p34969; p34969-1; p34969-2; p34969-3

119/378

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Target, Subunit, Species 5-hydroxytryptamine receptor 7 [human]

3 of 10

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 7 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

Quantitative value

439.7

Measurement pX

6.36

Concomitants: Compound RN

764984; 94179

Concomitants: Compound name

Clozapine; [3H]-LSD; BSA

Concomitants: Compound role

NSB; RAD; COM

Target Name

5-hydroxytryptamine receptor 7 [human]

Target Synonyms

5-ht-7; 5-ht-x; 5-ht7; 5-hydroxytryptamine receptor 7; htr7; serotonin receptor 7

Target Uniprot ID

p34969; p34969-1; p34969-2; p34969-3

Target, Subunit, Species 5-hydroxytryptamine receptor 7 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 7 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against human 5HT7 receptor expressed in CHO cells using 0.82 nM [125I]LSD as radioligand upon incubation in binding buffer (50 mM TrisHCl, pH 7.4, 10 mM MgCl2, 0.5 mM EDTA, 0.5% BSA) for 240 min at RT

Biological Species/NCBI Human ID Cells/Cell Lines

CHO

Substance RN

19916687View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[125I]LSD

Concomitants: Compound role

RAD

120/378

2017-11-11 00:22:14

Patent; Laboratorios Del. Dr. Esteve, S.A.; EP2149373; (2010); (A1) English, View in Reaxys 4 of 10

Target Name

5-hydroxytryptamine receptor 7 [human]

Target Synonyms

5-ht-7; 5-ht-x; 5-ht7; 5-hydroxytryptamine receptor 7; htr7; serotonin receptor 7

Target Uniprot ID

p34969; p34969-1; p34969-2; p34969-3

Target, Subunit, Species 5-hydroxytryptamine receptor 7 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 7 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against human 5-Hydroxytryptamine 7 receptor expressed in CHO cells upon incubation in 50 mM Tris-HCl, pH 7.4 at RT for 240 min using 0.82 nM [125I]LSD as radioligand

Biological Species/NCBI Human ID

5 of 10

Cells/Cell Lines

CHO

Substance RN

19916687View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

439.7

Measurement pX

6.36

Concomitants: Compound name

[125I]LSD

Concomitants: Compound role

RAD

Target Name

5-hydroxytryptamine receptor 7 [human]

Target Synonyms

5-ht-7; 5-ht-x; 5-ht7; 5-hydroxytryptamine receptor 7; htr7; serotonin receptor 7

Target Uniprot ID

p34969; p34969-1; p34969-2; p34969-3

Target, Subunit, Species 5-hydroxytryptamine receptor 7 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 7 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of [125I]LSD (0.82 nM) binding to human 5-Hydroxytryptamine 7 receptor expressed in CHO cells upon incubation in 50 mM Tris-HCl, pH 7.4 at RT for 240 min at a compound concentration of 10e-6 M

Biological Species/NCBI Human ID Cells/Cell Lines

CHO

Substance RN

19916687View in Reaxys

Measurement Parameter

% Inhibition

121/378

2017-11-11 00:22:14

6 of 10

Unit

Qualitative value

Quantitative value

Concomitants: Compound name

[125I]LSD

Concomitants: Compound role

RAD

Target Name

D(1A) dopamine receptor [human]

Target Synonyms

d(1a) dopamine receptor; dopamine d1 receptor; drd1

Target Uniprot ID

p21728

Target, Subunit, Species D(1A) dopamine receptor [human] Target Mutant/Chimera Details

D(1A) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

14a-compound 14a; table 1

Measurement Parameter

Unit

Qualitative value

Quantitative value

10000

Measurement pX

Concomitants: Compound RN

3620147; 3620147

Concomitants: Compound name

SCH 23390; [3H]-SCH 23390

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 7 of 10

Target Name

D(2) dopamine receptor [human]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p14416; p14416-1; p14416-2

Target PDB ID

5aer

Target, Subunit, Species D(2) dopamine receptor [human] Target Mutant/Chimera Details

D(2) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

122/378

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Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

14a-compound 14a; table 1

Measurement Parameter

Unit

Quantitative value

473

Deviation

Measurement pX

6.33

Concomitants: Compound RN

632204; 632204

Concomitants: Compound name

Spiperone; [3H]-Spiperone

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 8 of 10

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

14a-compound 14a; table 1

Measurement Parameter

Unit

Quantitative value

103

Deviation

Measurement pX

6.99

Concomitants: Compound RN

3620147; 3620147

Concomitants: Compound name

SCH 23390; [3H]-SCH 23390

Concomitants: Compound role

NSB; RAD

123/378

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Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 9 of 10

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

14a-compound 14a; table 1

Measurement Parameter

Unit

Quantitative value

0.03

Measurement pX

10.5

Concomitants: Compound RN

632204; 632204

Concomitants: Compound name

Spiperone; [3H]-Spiperone

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 10 of 10

Target Name

D(1B) dopamine receptor [human]

Target Synonyms

d(1b) dopamine receptor; d(5) dopamine receptor; d1beta dopamine receptor; dopamine d5 receptor; drd1b; drd1l2; drd5

Target Uniprot ID

p21918

Target, Subunit, Species D(1B) dopamine receptor [human] Target Mutant/Chimera Details

D(1B) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

19916687View in Reaxys

Substance Name

14a-compound 14a; table 1

Measurement Parameter

124/378

2017-11-11 00:22:14

Unit

Qualitative value

Quantitative value

10000

Measurement pX

Concomitants: Compound RN

3620147; 3620147

Concomitants: Compound name

SCH 23390; [3H]-SCH 23390

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys

Reaxys ID 22848095 View in Reaxys

63/181 CAS Registry Number: 414882-99-8 Chemical Name: 3-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C19H20N4O2 Molecular Formula: C19H20N4O2 Molecular Weight: 336.393 InChI Key: QEOATOUNLDHSQK-UHFFFAOYSA-N Note:

O N N

Druglikeness (1) 1 of 1

LogP

3.704

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.09

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

186.1

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys Medchem (3) 1 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofcolon cancer HCT116 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

HCT 116

Substance RN

22848095View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 2 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofbreast cancer MCF7 cells of humanNCI-60 sulforhodamine B assay

Cells/Cell Lines

MCF7

Substance RN

22848095View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys 3 of 3

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

cell growth; inhibition ofliver cancer HUH7 cells of humanNCI-60 sulforhodamine B assay

Substance RN

22848095View in Reaxys

Qualitative Results

no effect

Measurement Parameter

Qualitative

Qualitative value

Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin; Turkish Journal of Chemistry; vol. 36; nb. 4; (2012); p. 515 - 525, View in Reaxys

Reaxys ID 19135936 View in Reaxys

CAS Registry Number: 1008772-06-2 Chemical Name: 4-(1H-indole-3-ylmethyl)-N-pyrazin-2-ylpiperazine-1-carboxamide Linear Structure Formula: C18H20N6O Molecular Formula: C18H20N6O Molecular Weight: 336.396 InChI Key: WVNIKZYMGSQHQC-UHFFFAOYSA-N Note:

O N

64/181

N NH

126/378

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Patent-Specific Data (1) References Patent; Astellas Pharma Inc.; EP2065369; (2009); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

0.743

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

77.15

Lipinski Number

Veber Number

Reaxys ID 28456679 View in Reaxys

65/181 Chemical Name: 5-fluoro-3-((4-(2-methoxyphenyl)piperazin-1yl)methyl)-1H-indole Linear Structure Formula: C20H22FN3O Molecular Formula: C20H22FN3O Molecular Weight: 339.413 InChI Key: FNHBWTJWVSZPGZ-UHFFFAOYSA-N Note:

HN O

F N

Druglikeness (1) 1 of 1

LogP

3.888

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Reaxys ID 22604931 View in Reaxys

66/181 CAS Registry Number: 1345510-79-3 Chemical Name: 3-{[4-(2,5-difluorobenzyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H21F2N3 Molecular Formula: C20H21F2N3 Molecular Weight: 341.404 InChI Key: QXMZXABRBSZENN-UHFFFAOYSA-N Note:

F F

Druglikeness (1) 1 of 1

LogP

3.556

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

127/378

2017-11-11 00:22:14

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

126.7

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Target Name

Opioid Receptor, Sigma 2 [Rattus norvegicus]

Target Synonyms

opioid receptor, sigma 2

Target, Subunit, Species Opioid Receptor, Sigma 2 [Rattus norvegicus] Target Mutant/Chimera Details

Opioid Receptor, Sigma 2 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

128/378

2017-11-11 00:22:14

Biological Species/NCBI Rattus norvegicus ID Substance RN

22604931View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

418

Deviation

Measurement pX

6.38

Concomitants: Compound name

(+)-PENTAZOCINE; [3H]DITOLYLGUANIDINE

Concomitants: Compound role

COM; RAD

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 2 of 6

Target Name

Sigma non-opioid intracellular receptor 1 [guinea pig]

Target Synonyms

sigma non-opioid intracellular receptor 1

Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig] Target Mutant/Chimera Details

Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Biological Species/NCBI guinea pig ID Cells/Cell Lines

Brain cell

Substance RN

22604931View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

216

Deviation

Measurement pX

6.67

Concomitants: Compound name

(+)-[3H]PENTAZOCINE

Concomitants: Compound role

RAD

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 3 of 6

Bioassay Category

In Vitro (Efficacy)

129/378

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Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

22604931View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

5.47

Measurement pX

5.26

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 4 of 6

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

22604931View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

13.87

Measurement pX

4.86

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 5 of 6

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

22604931View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

9.19

Measurement pX

5.04

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 6 of 6

Target Name

Sigma non-opioid intracellular receptor 1 [guinea pig]

Target Synonyms

sigma non-opioid intracellular receptor 1

Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig] Target Mutant/Chimera Details

Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

130/378

2017-11-11 00:22:14

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity is the ratio of binding affinity of the compound towards GUINEA PIG brain cells Sigma 1 receptor to that of RAT liver cells Sigma 2 receptor

Biological Species/NCBI guinea pig ID Cells/Cell Lines

Brain cell

Substance RN

22604931View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys

Reaxys ID 5302588 View in Reaxys

67/181 CAS Registry Number: 75410-86-5 Linear Structure Formula: C22H22N4 Molecular Formula: C22H22N4 Molecular Weight: 342.443 Type of Substance: heterocyclic InChI Key: JDBVHYBVEROAAP-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References IVa

Golubev, V. E.; Trubitsyna, T. K.; Mashkovskii, M. D.; Suvorov, N. N.; Pharmaceutical Chemistry Journal; vol. 15; nb. 2; (1981); p. 88 - 90; Khimiko-Farmatsevticheskii Zhurnal; vol. 15; nb. 2; (1981); p. 30 - 33, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.643

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

35.16

Lipinski Number

Veber Number

Derivative (1) Derivative 2-[4-(1H-Indol-3ylmethyl)-piperazin-1-yl]-quinoline; compound with (Z)-but-2enedioic acid

References Golubev, V. E.; Trubitsyna, T. K.; Mashkovskii, M. D.; Suvorov, N. N.; Pharmaceutical Chemistry Journal; vol. 15; nb. 2; (1981); p. 88 - 90; Khimiko-Farmatsevticheskii Zhurnal; vol. 15; nb. 2; (1981); p. 30 - 33, View in Reaxys

Reaxys ID 337578 View in Reaxys

68/181

131/378

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CAS Registry Number: 35713-31-6 Chemical Name: N,N'-bis(indol-3-ylmethyl)piperazine; 3,3'-piperazine-1,4-diyldimethyl-bis-indole; 1,4-bis-indol-3-ylmethyl-piperazine; 1,4-Bis-indol-3-ylmethyl-piperazin; N,N-Diskatylpiperazin Linear Structure Formula: C22H24N4 Molecular Formula: C22H24N4 Molecular Weight: 344.459 Type of Substance: heterocyclic InChI Key: WSJVQTJWVHONKW-UHFFFAOYSA-N Note:

Substance Label (4) Label References 19

Foloppe, Nicolas; Chen, I-Jen; Davis, Ben; Hold, Adam; Morley, Dave; Howes, Rob; Bioorganic and Medicinal Chemistry; vol. 12; nb. 5; (2004); p. 935 - 947, View in Reaxys

Afsah, El-Sayed M.; Jackson, Anthony H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1984); p. 1929 - 1932, View in Reaxys

Kamal et al.; Pakistan Journal of Scientific and Industrial Research; vol. 14; (1971); p. 179, View in Reaxys

VII

Kamal et al.; Pakistan Journal of Scientific and Industrial Research; vol. 9; nb. 4; (1966); p. 323,324, 325; Chem.Abstr.; vol. 71; nb. 3199y; (1969), View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.342

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.06

Lipinski Number

Veber Number

Melting Point (4) 1 of 4

Melting Point [°C]

227

Solvent (Melting Point)

acetone; cyclohexane

Afsah, El-Sayed M.; Jackson, Anthony H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1984); p. 1929 - 1932, View in Reaxys 2 of 4

Melting Point [°C]

222

Kamal et al.; Pakistan Journal of Scientific and Industrial Research; vol. 9; nb. 4; (1966); p. 323,324, 325; Chem.Abstr.; vol. 71; nb. 3199y; (1969), View in Reaxys 3 of 4

Melting Point [°C]

231

Solvent (Melting Point)

ethanol; pyridine

Comment (Melting Point)

Decomp.

Akkerman; Veldstra; Recueil des Travaux Chimiques des Pays-Bas; vol. 73; (1954); p. 629,646, View in Reaxys 4 of 4

Melting Point [°C]

224 - 225

Solvent (Melting Point)

xylene

Runti; Orlando; Annali di Chimica (Rome, Italy); vol. 43; (1953); p. 308,312, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

132/378

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Afsah, El-Sayed M.; Jackson, Anthony H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1984); p. 1929 - 1932, View in Reaxys 2 of 2

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H (Fig. 4)

Kamal et al.; Pakistan Journal of Scientific and Industrial Research; vol. 14; (1971); p. 179, View in Reaxys Mass Spectrometry (1) References Kamal et al.; Pakistan Journal of Scientific and Industrial Research; vol. 14; (1971); p. 179, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Kamal et al.; Pakistan Journal of Scientific and Industrial Research; vol. 9; nb. 4; (1966); p. 323,324, 325; Chem.Abstr.; vol. 71; nb. 3199y; (1969), View in Reaxys Medchem (1) 1 of 1

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Apparent binding affinity of the compound measured as ability to displace 10 nM TAMRAparomomycin from A-site of Escherichia coli 30S ribosomal subunit upon incubation in 100 mM Tris-HCl, pH 7.5 for 60 min by FRET assay

Biological Species/NCBI Escherichia coli ID Substance RN

337578View in Reaxys

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

216

Measurement pX

3.67

Foloppe, Nicolas; Chen, I-Jen; Davis, Ben; Hold, Adam; Morley, Dave; Howes, Rob; Bioorganic and Medicinal Chemistry; vol. 12; nb. 5; (2004); p. 935 - 947, View in Reaxys

Reaxys ID 29258003 View in Reaxys

69/181 Chemical Name: 3-[(t-butyloxycarbonylpiperazin-4-yl)methyl]-5-methoxy-1H-indole Linear Structure Formula: C19H27N3O3 Molecular Formula: C19H27N3O3 Molecular Weight: 345.442 InChI Key: KLWSFLZYJPOGSH-UHFFFAOYSA-N Note:

O N

N O

N H

Substance Label (2) Label References 8s

133/378

2017-11-11 00:22:14

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Ramasastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (36 pag.); WO2016/27276; (2016); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.699

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

57.8

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

H- NMR (CDCI3, δ ppm): 1.45 (9H, s), 2.45 (4H, s), 3.43 (4H, s), 3.69 (2H, s), 3.86 (3H, s), 6.85 - 6.88 (1H, dd, J = 8.7, 2.2 Hz), 7.08 - 7.09 (1H, d, J = 1 .57 Hz), 7.19 ( 1 H, d, J = 2.2 Hz), 7.23 - 7.25 (l H, d, J = 8.77 Hz), 8.25 (lH, bs)

Location

Page/Page column 11

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Ramasastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (36 pag.); WO2016/27276; (2016); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; KAMBHAMPATI, Ramasastri; SHINDE, Anil Karbhari; JASTI, Venkateswarlu; (36 pag.); WO2016/27276; (2016); (A1) English, View in Reaxys

Page/Page column 11; 17

Reaxys ID 22705334 View in Reaxys

70/181 Chemical Name: 3-((4-(4-methoxyphenyl)piperazin-1-yl)methyl)-1H-indole-5-carbonitrile; 3-{[4-(4-methoxyphenyl)-1-piperazinyl]methyl}-1H-indole-5-carbonitrile Linear Structure Formula: C21H22N4O Molecular Formula: C21H22N4O Molecular Weight: 346.432 InChI Key: GOKLXLVAHUBTTB-UHFFFAOYSA-N Note:

N N

N H

Substance Label (1) Label References 7

Druglikeness (1) 1 of 1

LogP

3.45

H Bond Donors

H Bond Acceptors

134/378

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Rotatable Bonds

TPSA

55.29

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 290 VIS) [nm] Log epsilon

4.5

Reaxys ID 9077921 View in Reaxys

71/181 Linear Structure Formula: C21H23N3O2 Molecular Formula: C21H23N3O2 Molecular Weight: 349.433 Type of Substance: heterocyclic InChI Key: FFBXVXKKCLEHIZ-UHFFFAOYSA-N Note:

NH O O

Substance Label (1) Label References 3c

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys

Druglikeness (1)

135/378

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1 of 1

LogP

3.748

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.57

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

168 - 169

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys Medchem (5) 1 of 5

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

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Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

9077921View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

46000

Measurement pX

4.34

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 2 of 5

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

9077921View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

48000

Measurement pX

4.32

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys

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3 of 5

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

9077921View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

90000

Measurement pX

4.05

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 4 of 5

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

9077921View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

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Measurement Parameter

Unit

Qualitative value

Quantitative value

100000

Measurement pX

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys 5 of 5

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

9077921View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

800

Measurement pX

6.1

Concomitants: Compound RN

632204; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-Spiperone; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Moll, Annette; Huebner, Harald; Gmeiner, Peter; Troschuetz, Reinhard; Bioorganic and medicinal chemistry; vol. 10; nb. 6; (2002); p. 1671 - 1679, View in Reaxys

Reaxys ID 10289365 View in Reaxys

72/181

139/378

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Chemical Name: 3-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl-methyl]-1H-indole Linear Structure Formula: C21H23N3O2 Molecular Formula: C21H23N3O2 Molecular Weight: 349.433 Type of Substance: heterocyclic InChI Key: UVQHGCKWFYZHSI-UHFFFAOYSA-N Note:

NH N

N O

Substance Label (1) Label References 5a

Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys; Smid, Pieter; Coolen, Hein K. A. C.; Keizer, Hiskias G.; Van Hes, Rolf; De Moes, Jan-Peter; Den Hartog, Arnold P.; Stork, Bob; Plekkenpol, Rob H.; Niemann, Leonarda C.; Stroomer, Cees N. J.; Tulp, Martin Th. M.; Van Stuivenberg, Herman H.; McCreary, Andrew C.; Hesselink, Mayke B.; Herremans, Arnoud H. J.; Kruse, Chris G.; Journal of Medicinal Chemistry; vol. 48; nb. 22; (2005); p. 6855 - 6869, View in Reaxys

Patent-Specific Data (1) References Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.164

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.73

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

85 - 86

Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys 2 of 2

Melting Point [°C]

85 - 86

Smid, Pieter; Coolen, Hein K. A. C.; Keizer, Hiskias G.; Van Hes, Rolf; De Moes, Jan-Peter; Den Hartog, Arnold P.; Stork, Bob; Plekkenpol, Rob H.; Niemann, Leonarda C.; Stroomer, Cees N. J.; Tulp, Martin Th. M.; Van Stuivenberg, Herman H.; McCreary, Andrew C.; Hesselink, Mayke B.; Herremans, Arnoud H. J.; Kruse, Chris G.; Journal of Medicinal Chemistry; vol. 48; nb. 22; (2005); p. 6855 - 6869, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

10.8; 7.65; 7.35; 7.18; 7.07; 6.98; 6.67; 6.4 - 6.48; 4.2; 3.7; 3; 2.55

(400 MHz, DMSO-d6): δ 10.8 (s, 1H, NH-indole); 7.65 (d, 1H, J=8 Hz, H-arom); 7.35 (d, 1H, J=8 Hz, H-arom); 7.18 (d, 1H, J=2 Hz, H2-indole); 7.07 (t, 1H, J=7 Hz, H-arom); 6.98 (t,1H, J=7 Hz, H-arom); 6.67 (t,1H, J=7 Hz, H-arom); 6.4-6.48 (2* d, 2H, H-arom); 4.2 (bm, 4H, OCH2CH2O); 3.7 (bs, 2H, CH2); 3.0, 2.55 (2* bs, 8H, piperazine)

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Kind of signal

s, 1H, NH-indole; d, 1H, J=8 Hz, H-arom; d, 1H, J=8 Hz, H-arom; d, 1H, J=2 Hz, H2-indole; t, 1H, J=7 Hz, H-arom; t,1H, J=7 Hz, H-arom; t,1H, J=7 Hz, H-arom; 2* d, 2H, Harom; bm, 4H, OCH&2%CH&2%O; bs, 2H, CH&2%; 2* bs, 8H, piperazine

Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Smid, Pieter; Coolen, Hein K. A. C.; Keizer, Hiskias G.; Van Hes, Rolf; De Moes, Jan-Peter; Den Hartog, Arnold P.; Stork, Bob; Plekkenpol, Rob H.; Niemann, Leonarda C.; Stroomer, Cees N. J.; Tulp, Martin Th. M.; Van Stuivenberg, Herman H.; McCreary, Andrew C.; Hesselink, Mayke B.; Herremans, Arnoud H. J.; Kruse, Chris G.; Journal of Medicinal Chemistry; vol. 48; nb. 22; (2005); p. 6855 - 6869, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) HRMS (High resolution mass spectrometry)

Molecular peak

References Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys

Medchem (6) 1 of 6

Target Name

D(2) dopamine receptor [taurine cattle]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p20288; p20288-2

Target, Subunit, Species D(2) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(2) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

caudate nucleus

Cells/Cell Lines

cells

Cell Fraction

Homogenate/Centrifugation/Pellet

Substance RN

10289365View in Reaxys

Substance Name

141/378

2017-11-11 00:22:14

Measurement Parameter

Unit

Quantitative value

Deviation

Measurement pX

7.21

Concomitants: Compound RN

632204; 1551655; 1938132; 84272

Concomitants: Compound name

[3H]-Spiperone; (+)-Butaclamol; Pargyline; L-(+)-Ascorbic acid

Concomitants: Compound role

RAD; NSB; COM; COM

Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys 2 of 6

Target Name

5-hydroxytryptamine receptor [Rattus norvegicus]

Target Synonyms

5-hydroxytryptamine receptor

Target, Subunit, Species 5-hydroxytryptamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Flux uptake

Biological Species/NCBI Rattus norvegicus ID Organs/Tissues

brain cortex

Cells/Cell Lines

cells

Substance RN

10289365View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

176

Deviation

Measurement pX

6.75

Concomitants: Compound RN

7467879; 143524

Concomitants: Compound name

[3H]-Paroxetine; 5-HT

Concomitants: Compound role

MAR; SUB

Patent; SOLVAY PHARMACEUTICALS B.V.; US2006/122175; (2006); (A1) English, View in Reaxys 3 of 6

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

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Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

10289365View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

Deviation

Measurement pX

7.21

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone

Concomitants: Compound role

RAD

Target Name

Sodium-dependent serotonin transporter [Rattus norvegicus]

Target Synonyms

5ht transporter; 5htt; slc6a4; sodium-dependent serotonin transporter; solute carrier family 6 member 4

Target Uniprot ID

p31652

Target, Subunit, Species Sodium-dependent serotonin transporter [Rattus norvegicus] Target Mutant/Chimera Details

Sodium-dependent serotonin transporter [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

brain cortex

Cell Fraction

Membrane

Substance RN

10289365View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

176

Deviation

143/378

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Measurement pX

6.75

Concomitants: Compound RN

3991406; 7467879

Concomitants: Compound name

Fluoxetine; [3H]-Paroxetine

Concomitants: Compound role

NSB; RAD

Target Name

Sodium-dependent serotonin transporter [Rattus norvegicus]

Target Synonyms

5ht transporter; 5htt; slc6a4; sodium-dependent serotonin transporter; solute carrier family 6 member 4

Target Uniprot ID

p31652

Target, Subunit, Species Sodium-dependent serotonin transporter [Rattus norvegicus]

6 of 6

Target Mutant/Chimera Details

Sodium-dependent serotonin transporter [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding affinity towards serotonin reuptake sites in rat cortical membranes using [3H]-paroxetine

Cells/Cell Lines

brain cortical membranes

Substance RN

10289365View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

176

Measurement pX

6.75

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding affinity towards dopamine receptor D2 in rat brain (and pituitary) using [3H]-Spiroperidol as radioligand

Cells/Cell Lines

brain cell

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Substance RN

10289365View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

Measurement pX

7.21

Reaxys ID 11672248 View in Reaxys

73/181 Chemical Name: 3-(4-(benzyloxycarbonyl)piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C21H23N3O2 Molecular Formula: C21H23N3O2 Molecular Weight: 349.433 InChI Key: FSVZKNGFNVSDKP-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References D 184

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.194

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.57

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 21558056 View in Reaxys

CAS Registry Number: 355396-63-3 Chemical Name: HTS 06142 Linear Structure Formula: C21H23N3O2 Molecular Formula: C21H23N3O2 Molecular Weight: 349.433 InChI Key: COEIFRBEMCGQEN-UHFFFAOYSA-N Note:

N N NH

74/181

Patent-Specific Data (1) References Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys

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Druglikeness (1) 1 of 1

LogP

2.723

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.73

Lipinski Number

Veber Number

Medchem (1) 1 of 1

Target Name

Transient receptor potential cation channel subfamily M member 7

Target Synonyms

chak; chak1; channel-kinase 1; long transient receptor potential channel 7; ltrpc-7; ltrpc7; transient receptor potential cation channel subfamily m member 7; transient receptor potential-phospholipase c-interacting kinase; trp-plik; trpm7

Target, Subunit, Species Transient receptor potential cation channel subfamily M member 7 Target Mutant/Chimera Details

Transient receptor potential cation channel subfamily M member 7:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of HEK 293 T-rex cell death stably transfected with recombinant Flag tagged Transient receptor potential melastatin 7 (TRPM7) measured as viable cell count upon incubation in HBSS at a compound concentration of 39 nM (39 nM - 20 uM) upon incubation for 48 hours

Cells/Cell Lines

T-REX-HEK 293

Substance RN

21558056View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

VIABLE CELL COUNT

Qualitative value

Quantitative value

Patent; NONO, INC.; SUN, Xiujun; TYMIANSKI, Michael; GARMAN, Jonathan, David; WO2011/72275; (2011); (A2) English, View in Reaxys

Reaxys ID 1603558 View in Reaxys

75/181 CAS Registry Number: 3414-72-0 Chemical Name: 3-(4-benzyl-piperazin-1-ylmethyl)-5-nitro-indole Linear Structure Formula: C20H22N4O2 Molecular Formula: C20H22N4O2 Molecular Weight: 350.42 Type of Substance: heterocyclic InChI Key: PKVAMSCYQLIVLR-UHFFFAOYSA-N Note:

NH O

N O

Druglikeness (1) 1 of 1

LogP

3.126

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.09

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Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

108 - 112

Solvent (Melting Point)

toluene

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys 2 of 2

Melting Point [°C]

108 - 112

Solvent (Melting Point)

ethanol

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys Medchem (1) 1 of 1

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal dose was determined in mice upon intravenous administration

Biological Species/NCBI Mus musculus ID Substance RN

1603558View in Reaxys

Substance Route of Adm.

intravenous administration

Measurement Parameter

LD50

Unit

mg/kg

Qualitative value

Quantitative value

39.8

DeGraw; Brown; Skinner; Journal of medicinal chemistry; vol. 9; nb. 1; (1966); p. 140 - 142, View in Reaxys

Reaxys ID 8792889 View in Reaxys

76/181 Linear Structure Formula: C20H19N4Cl Molecular Formula: C20H19ClN4 Molecular Weight: 350.851 Type of Substance: heterocyclic InChI Key: SNFLVHDMWFYRRB-UHFFFAOYSA-N Note:

NH Cl N

Substance Label (1) Label References 3b

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.157

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

193

147/378

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Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys Medchem (6) 1 of 6

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

8792889View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

510

148/378

2017-11-11 00:22:14

Deviation

Measurement pX

6.29

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 6

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8792889View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

1400

Deviation

570

Measurement pX

5.85

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 3 of 6

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

149/378

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Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8792889View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

540

Deviation

230

Measurement pX

6.27

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 4 of 6

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8792889View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

550

Deviation

Measurement pX

6.26

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

150/378

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Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 5 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8792889View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

Deviation

Measurement pX

7.77

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 6 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

151/378

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Substance RN

8792889View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Quantitative value

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Reaxys ID 8793434 View in Reaxys

77/181 Linear Structure Formula: C20H19N4Cl Molecular Formula: C20H19ClN4 Molecular Weight: 350.851 Type of Substance: heterocyclic InChI Key: HYLGECOKUPPDRN-UHFFFAOYSA-N Note:

N Cl

Substance Label (1) Label References 3d

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.157

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

189

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

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IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys Medchem (6) 1 of 6

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

8793434View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

550

Deviation

Measurement pX

6.26

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 6

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

153/378

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Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793434View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

4300

Deviation

650

Measurement pX

5.37

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 3 of 6

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793434View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

2600

Deviation

1100

Measurement pX

5.59

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

154/378

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Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 4 of 6

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793434View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

6400

Deviation

250

Measurement pX

5.19

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 5 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793434View in Reaxys

155/378

2017-11-11 00:22:14

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

Deviation

7.50000

Measurement pX

7.54

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 6 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8793434View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Quantitative value

0.9

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Reaxys ID 11951133 View in Reaxys

78/181

156/378

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CAS Registry Number: 701205-17-6 Chemical Name: 5-methoxy-3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-1H-indole; 5-methoxy-3-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-1H-indole; 5-methoxy-3-(4-(1-methoxyphen-2-yl)piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C21H25N3O2 Molecular Formula: C21H25N3O2 Molecular Weight: 351.448 InChI Key: MBYXPBOWSBKBJN-UHFFFAOYSA-N Note:

O NH

Substance Label (2) Label References 12

D 159

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.642

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.73

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry) EI (Electron impact); Spectrum ESI (Electrospray ionisation)

References Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys

Molecular peak

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

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UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 290 VIS) [nm] Log epsilon

4.5

Reaxys ID 628593 View in Reaxys

79/181 CAS Registry Number: 58434-20-1 Chemical Name: 4-fluoro-N-(4-indol-3-ylmethyl-piperazin-1-yl)benzamide Linear Structure Formula: C20H21FN4O Molecular Formula: C20H21FN4O Molecular Weight: 352.411 Type of Substance: heterocyclic InChI Key: BHBRWSQWUNNUOO-UHFFFAOYSA-N Note:

NH O

Substance Label (2) Label References 33

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.83

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

51.37

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

210 - 212

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys 2 of 2

Melting Point [°C]

206 - 208

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys Medchem (2) 1 of 2

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Antihypertensive activity was tested using spontaneous hypertensive rat by a standard indirect tail cuff method on day 1 at oral dose of 100 mg/kg, +/- is marginal or transient activity

Biological Species/NCBI Rattus norvegicus ID Substance RN

628593View in Reaxys

Substance Route of Adm.

oral administration

Qualitative Results

Marginal or transient activity

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Glamkowski; Reitano; Woodward; Journal of Medicinal Chemistry; vol. 20; nb. 11; (1977); p. 1485 - 1489, View in Reaxys 2 of 2

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Antihypertensive activity was tested using spontaneous hypertensive rat by a standard indirect tail cuff method on day 3 at oral dose of 100 mg/kg, +/- is marginal or transient activity

Biological Species/NCBI Rattus norvegicus ID Substance RN

628593View in Reaxys

Substance Route of Adm.

oral administration

Qualitative Results

Marginal or transient activity

Glamkowski; Reitano; Woodward; Journal of Medicinal Chemistry; vol. 20; nb. 11; (1977); p. 1485 - 1489, View in Reaxys

Reaxys ID 11725009 View in Reaxys

80/181 Chemical Name: 3-[4-(4-chloro-3-methoxyphenyl)piperazin-1yl]methylindole Linear Structure Formula: C20H22ClN3O Molecular Formula: C20H22ClN3O Molecular Weight: 355.867 InChI Key: LSSGXUSYGHZTJW-UHFFFAOYSA-N Note:

N N NH

Cl O

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 8

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.349

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Reaxys ID 9726366 View in Reaxys

81/181 Chemical Name: 3-[4-(m-trifluoromethylphenyl)-piperazin-1-ylmethyl]-1H-indole Linear Structure Formula: C20H20F3N3 Molecular Formula: C20H20F3N3 Molecular Weight: 359.394 Type of Substance: heterocyclic InChI Key: CVIYNLVHJXVVIA-UHFFFAOYSA-N Note:

NH F N

F F

Substance Label (1) Label References

159/378

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Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 - 111, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.737

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

89 - 91

Solvent (Melting Point)

hexane

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys Medchem (1) 1 of 1

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Substance RN

9726366View in Reaxys

Substance Name

Substance Dose

6.25000 mg/L

Measurement Parameter

MIC

Unit

mg/L

Quantitative value

6.25

Measurement pX

4.76

Malinka, Wieslaw; Swiatek, Piotr; Acta Poloniae Pharmaceutica - Drug Research; vol. 61; nb. 2; (2004); p. 107 111, View in Reaxys

Reaxys ID 11725008 View in Reaxys

82/181

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Chemical Name: 5-chloro-3-[4-(4-chlorophenyl)piperazin-1yl]methylindole Linear Structure Formula: C19H19Cl2N3 Molecular Formula: C19H19Cl2N3 Molecular Weight: 360.286 InChI Key: XUCYZJZBUAWKGX-UHFFFAOYSA-N Note:

Cl N N NH

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 8

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.056

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Reaxys ID 23870534 View in Reaxys

83/181 CAS Registry Number: 1451194-28-7 Chemical Name: 3-{[4-(2,3-dichlorophenyl)-piperazin-1yl]methyl}-1H-indole Linear Structure Formula: C19H19Cl2N3 Molecular Formula: C19H19Cl2N3 Molecular Weight: 360.286 InChI Key: SVSNQBMLUDOWHS-UHFFFAOYSA-N Note:

Substance Label (1) Label References 14b

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.056

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

49 - 51

Location

supporting information

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy)

161/378

2017-11-11 00:22:14

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Location

supporting information

References Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys

Medchem (5) 1 of 5

Target Name

D(1A) dopamine receptor [human]

Target Synonyms

d(1a) dopamine receptor; dopamine d1 receptor; drd1

Target Uniprot ID

p21728

Target, Subunit, Species D(1A) dopamine receptor [human] Target Mutant/Chimera Details

D(1A) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

23870534View in Reaxys

Substance Name

14b-compound 14b; table 1

Measurement Parameter

Unit

Qualitative value

Quantitative value

10000

Measurement pX

Concomitants: Compound RN

3620147; 3620147

Concomitants: Compound name

SCH 23390; [3H]-SCH 23390

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 2 of 5

Target Name

D(2) dopamine receptor [human]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

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Target Uniprot ID

p14416; p14416-1; p14416-2

Target PDB ID

5aer

Target, Subunit, Species D(2) dopamine receptor [human] Target Mutant/Chimera Details

D(2) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

23870534View in Reaxys

Substance Name

14b-compound 14b; table 1

Measurement Parameter

Unit

Quantitative value

502

Deviation

Measurement pX

6.3

Concomitants: Compound RN

632204; 632204

Concomitants: Compound name

Spiperone; [3H]-Spiperone

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 3 of 5

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

23870534View in Reaxys

Substance Name

14b-compound 14b; table 1

Measurement Parameter

163/378

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Unit

Quantitative value

123

Deviation

Measurement pX

6.91

Concomitants: Compound RN

3620147; 3620147

Concomitants: Compound name

SCH 23390; [3H]-SCH 23390

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 4 of 5

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

23870534View in Reaxys

Substance Name

14b-compound 14b; table 1

Measurement Parameter

Unit

Quantitative value

6.2

Deviation

0.100000

Measurement pX

8.21

Concomitants: Compound RN

632204; 632204

Concomitants: Compound name

Spiperone; [3H]-Spiperone

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys 5 of 5

Target Name

D(1B) dopamine receptor [human]

Target Synonyms

d(1b) dopamine receptor; d(5) dopamine receptor; d1beta dopamine receptor; dopamine d5 receptor; drd1b; drd1l2; drd5

Target Uniprot ID

p21918

Target, Subunit, Species D(1B) dopamine receptor [human] Target Mutant/Chimera Details

D(1B) dopamine receptor [human]:Wild

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Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

23870534View in Reaxys

Substance Name

14b-compound 14b; table 1

Measurement Parameter

Unit

Qualitative value

Quantitative value

10000

Measurement pX

Concomitants: Compound RN

3620147; 3620147

Concomitants: Compound name

SCH 23390; [3H]-SCH 23390

Concomitants: Compound role

NSB; RAD

Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 18; (2013); p. 5077 - 5081, View in Reaxys

Reaxys ID 25966194 View in Reaxys

84/181 CAS Registry Number: 1348317-84-9 Linear Structure Formula: C19H20ClN3*ClH Molecular Formula: C19H20ClN3*ClH Molecular Weight: 362.302 InChI Key: NIOIXSOSEQDRML-UHFFFAOYSA-N Note:

Cl N HCl

Druglikeness (1) 1 of 1

LogP

4.946

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Medchem (5) 1 of 5

Target Name

5-hydroxytryptamine receptor 1A [Rattus norvegicus]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; 5ht1a; htr1a; serotonin receptor 1a

Target Uniprot ID

p19327

Target, Subunit, Species 5-hydroxytryptamine receptor 1A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1A [Rattus norvegicus]:Wild

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Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against 5-hydroxytryptamine 1A receptor in rat hippocampus upon incubation with 0.5nM of [3H]-8-OH-DPAT at 25 degree C for 30 min

Biological Species/NCBI Rattus norvegicus ID

2 of 5

Substance RN

25966194View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

1000

Measurement pX

Concomitants: Compound name

[3H]8-OH-DPAT

Concomitants: Compound role

RAD

Target Name

D(2) dopamine receptor [human]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p14416; p14416-1; p14416-2

Target PDB ID

5aer

Target, Subunit, Species D(2) dopamine receptor [human] Target Mutant/Chimera Details

D(2) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against cloned human dopamine receptor D2 expressed in A9L cells using 0.15 nM [3H]spiperone as radioligand with 50 mM Tris buffer at pH 7.5

Biological Species/NCBI Human ID Cells/Cell Lines

Substance RN

25966194View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

360

Measurement pX

6.44

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

166/378

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3 of 5

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against cloned human dopamine receptor D3 expressed in CHO cells using 0.15 nM [3H]spiperone as radioligand with 50 mM Tris buffer at pH 7.5

Biological Species/NCBI Human ID

4 of 5

Cells/Cell Lines

CHO

Substance RN

25966194View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

D(4) dopamine receptor [human]

Target Synonyms

d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p21917

Target, Subunit, Species D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against cloned human dopamine receptor D3 expressed in CHO cells using 0.15 nM [3H]spiperone as radioligand with 50 mM Tris buffer at pH 7.5

Biological Species/NCBI Human ID Cells/Cell Lines

CHO

Substance RN

25966194View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

167/378

2017-11-11 00:22:14

5 of 5

Quantitative value

Measurement pX

8.3

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

D(3) dopamine receptor [human]; D(4) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3 + d(2c) dopamine receptor; d(4) dopamine receptor; dopamine d4 receptor; drd4

Target Uniprot ID

p35462 + p21917

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human]; D(4) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild; D(4) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human; human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against cloned human dopamine receptor D4 expressed in CHO cells using 0.15 nM [3H]spiperone as radioligand with 50 mM Tris buffer at pH 7.5

Biological Species/NCBI Human ID Cells/Cell Lines

CHO

Substance RN

25966194View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

Measurement pX

7.1

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Reaxys ID 28456678 View in Reaxys HO

85/181 Chemical Name: 2-(4-((5-chloro-1H-indol-3-yl)methyl)piperazin-1-yl)-N,N-dimethylethan-1-amine formic acid salt Linear Structure Formula: C17H25ClN4*CH2O2 Molecular Formula: CH2O2*C17H25ClN4 Molecular Weight: 366.891 InChI Key: POLNIUXNISKWMR-UHFFFAOYSA-N Note:

O HN Cl

Substance Label (1) Label References

168/378

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Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 - 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

62.81

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties orange

supporting information

References Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie International Edition; vol. 54; nb. 5; (2015); p. 1551 - 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys

Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

high water solubility

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); elec-

supporting information

References Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie -

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trospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

International Edition; vol. 54; nb. 5; (2015); p. 1551 - 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys

Reaxys ID 22705327 View in Reaxys

86/181 Chemical Name: 5-bromo-3-((4-phenylpiperazin-1-yl)methyl)-1H-indole; 5-bromo-3-[(4-phenyl-1-piperazinyl)methyl]-1H-indole Linear Structure Formula: C19H20BrN3 Molecular Formula: C19H20BrN3 Molecular Weight: 370.292 InChI Key: WUFFRSHCMYNTJG-UHFFFAOYSA-N Note:

Br N

N H

Substance Label (1) Label References 10

Druglikeness (1) 1 of 1

LogP

4.61

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 281 VIS) [nm] Log epsilon

4.1

Reaxys ID 11951030 View in Reaxys

87/181

CAS Registry Number: 701205-18-7 Chemical Name: 5-bromo-3-(4-(pyridin-2-yl)piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C18H19BrN4 Molecular Formula: C18H19BrN4 Molecular Weight: 371.28 InChI Key: PINBXRZSNRLKID-UHFFFAOYSA-N Note:

Br NH

Substance Label (1) Label References D 161

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.086

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

35.16

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 25587862 View in Reaxys

88/181

171/378

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O HO

Linear Structure Formula: C20H28N4O3 Molecular Formula: C20H28N4O3 Molecular Weight: 372.467 InChI Key: YKNWOJOWNPOJRJ-UHFFFAOYSA-N Note:

N H

N N

Druglikeness (1) 1 of 1

LogP

1.32

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

88.67

Lipinski Number

Veber Number

Medchem (6) 1 of 6

Target Name

Histone deacetylase [human]

Target Synonyms

histone deacetylase

Target, Subunit, Species Histone deacetylase [human]

2 of 6

Target Mutant/Chimera Details

Histone deacetylase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Histone deacetylase in human HeLa extract upon incubation for 1 h at 37 degree C in 20 mM Tris, pH 7.4

Cells/Cell Lines

HeLa

Substance RN

25587862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 1 [human]

Target Synonyms

hd1; hdac1; histone deacetylase 1; rpd3l1

Target Uniprot ID

q13547

Target PDB ID

4bkx

Target, Subunit, Species Histone deacetylase 1 [human] Target Mutant/Chimera Details

Histone deacetylase 1 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

172/378

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3 of 6

Bioassay Details

Inhibitory activity of the compound against human recombinant Histone deacetylase 1 transfected in to baculovirus infected SF9 cells upon incubation for 1 h at 37 degree C in 20 mM Tris, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 2 [Mus musculus]

Target Synonyms

hd2; hdac2; histone deacetylase 2; yy1 transcription factor-binding protein; yy1bp

Target Uniprot ID

p70288

Target, Subunit, Species Histone deacetylase 2 [Mus musculus]

4 of 6

Target Mutant/Chimera Details

Histone deacetylase 2 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against mouse recombinant Histone deacetylase 2 transfected in to baculovirus infected SF9 cells upon incubation for 1 h at 37 degree C in 20 mM Tris, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 1 [human]

Target Synonyms

hd1; hdac1; histone deacetylase 1; rpd3l1

Target Uniprot ID

q13547

Target PDB ID

4bkx

Target, Subunit, Species Histone deacetylase 1 [human] Target Mutant/Chimera Details

Histone deacetylase 1 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against recombinant full length human Histone deacetylase 1 expressed in Sf9 insect cells upon incubation at 37 degree C for 1 hr in 20 mM Tris buffer, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587862View in Reaxys

173/378

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5 of 6

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 2 [Mus musculus]

Target Synonyms

hd2; hdac2; histone deacetylase 2; yy1 transcription factor-binding protein; yy1bp

Target Uniprot ID

p70288

Target, Subunit, Species Histone deacetylase 2 [Mus musculus]

6 of 6

Target Mutant/Chimera Details

Histone deacetylase 2 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against recombinant full length mouse Histone deacetylase 2 expressed in Sf9 insect cells upon incubation at 37 degree C for 1 hr in 20 mM Tris buffer, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase [human]

Target Synonyms

histone deacetylase

Target, Subunit, Species Histone deacetylase [human] Target Mutant/Chimera Details

Histone deacetylase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Histone deacetylase from human HeLa cells upon incubation at 37 degree C for 1 hr in 25 mM HEPES buffer, pH 8.0 using 15 uM acetylated histone H4 peptide as substrate

Cells/Cell Lines

HeLa

Substance RN

25587862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

174/378

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Reaxys ID 22604930 View in Reaxys

89/181 CAS Registry Number: 1345510-80-6 Chemical Name: 3-{[4-(3,4-dichlorobenzyl)piperazin-1-yl]methyl}-1H-indole Linear Structure Formula: C20H21Cl2N3 Molecular Formula: C20H21Cl2N3 Molecular Weight: 374.313 InChI Key: GBYXTIZDOIKXPZ-UHFFFAOYSA-N Note:

Cl Cl

Druglikeness (1) 1 of 1

LogP

4.478

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

107

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

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Target Name

Opioid Receptor, Sigma 2 [Rattus norvegicus]

Target Synonyms

opioid receptor, sigma 2

Target, Subunit, Species Opioid Receptor, Sigma 2 [Rattus norvegicus] Target Mutant/Chimera Details

Opioid Receptor, Sigma 2 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Biological Species/NCBI Rattus norvegicus ID Substance RN

22604930View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

130

Deviation

Measurement pX

6.89

Concomitants: Compound name

(+)-PENTAZOCINE; [3H]DITOLYLGUANIDINE

Concomitants: Compound role

COM; RAD

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 2 of 6

Target Name

Sigma non-opioid intracellular receptor 1 [guinea pig]

Target Synonyms

sigma non-opioid intracellular receptor 1

Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig] Target Mutant/Chimera Details

Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Biological Species/NCBI guinea pig ID Cells/Cell Lines

Brain cell

Substance RN

22604930View in Reaxys

176/378

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Measurement Parameter

Unit

Qualitative value

Quantitative value

126

Deviation

Measurement pX

6.9

Concomitants: Compound name

(+)-[3H]PENTAZOCINE

Concomitants: Compound role

RAD

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 3 of 6

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

22604930View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

2.92

Measurement pX

5.53

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 4 of 6

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

22604930View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

3.42

Measurement pX

5.47

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 5 of 6

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HCT116

Substance RN

22604930View in Reaxys

177/378

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Measurement Parameter

IC50

Unit

µM

Measurement Object

IC50

Quantitative value

9.33

Measurement pX

5.03

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys 6 of 6

Target Name

Sigma non-opioid intracellular receptor 1 [guinea pig]

Target Synonyms

sigma non-opioid intracellular receptor 1

Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig] Target Mutant/Chimera Details

Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity is the ratio of binding affinity of the compound towards GUINEA PIG brain cells Sigma 1 receptor to that of RAT liver cells Sigma 2 receptor

Biological Species/NCBI guinea pig ID Cells/Cell Lines

Brain cell

Substance RN

22604930View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard; Chemical Biology and Drug Design; vol. 78; nb. 5; (2011); p. 869 - 875, View in Reaxys

Reaxys ID 29599928 View in Reaxys

90/181 Chemical Name: 4-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-7chloroquinoline; 4-(4-((1H-Indol-3-yl)methyl)piperazin-1-yl)-7chloroquinoline Linear Structure Formula: C22H21ClN4 Molecular Formula: C22H21ClN4 Molecular Weight: 376.889 InChI Key: YSZQCJMJIIWGKU-UHFFFAOYSA-N Note:

N HN

N N

Substance Label (1) Label References 22

Druglikeness (1) 1 of 1

LogP

4.537

H Bond Donors

H Bond Acceptors

Rotatable Bonds

178/378

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TPSA

35.16

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300.1

Original Text (NMR Spectroscopy)

Signals [ppm]

2.59 - 2.64; 3.12 - 3.19; 3.56; 7.06 - 8.63; 9.78

Kind of signal

m, 2H; m, 4H; s, 2H; m, 10H; bs, 1H

NMR (DMSO-d6): δH. 2.59-2.64 (m, 2H), 3.12-3.19 (m, 4H), 3.56 (s, 2H), 7.06-8.63 (m, 10H), 9.78 (bs, 1H)

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.1

Jeankumar, Variam Ullas; Reshma, Rudraraju Srilakshmi; Vats, Rahul; Janupally, Renuka; Saxena, Shalini; Yogeeswari, Perumal; Sriram, Dharmarajan; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 216 231, View in Reaxys Mass Spectrometry (1) Description (Mass Peak Spectrometry) electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum

377.2 m/z

References Jeankumar, Variam Ullas; Reshma, Rudraraju Srilakshmi; Vats, Rahul; Janupally, Renuka; Saxena, Shalini; Yogeeswari, Perumal; Sriram, Dharmarajan; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 216 - 231, View in Reaxys

Medchem (4) 1 of 4

Substance Effect

Cytotoxic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

RAW 264.7

Substance RN

29599928View in Reaxys

Substance Name

4-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-7-chloroquinoline

Substance Dose

100 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

22.23

Measurement pX

179/378

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Substance Effect

Anti-Tuberculosis

Bioassay Category

In Vitro (Efficacy)

Biological Species/NCBI Mycobacterium tuberculosis H37Rv ID Substance RN

29599928View in Reaxys

Substance Name

4-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-7-chloroquinoline

Measurement Parameter

MIC

Unit

μM

Quantitative value

16.25

Measurement pX

4.79

Target Name

DNA gyrase, subunit B [Mycobacterium tuberculosis]

Target Synonyms

dna gyrase, subunit b

Target, Subunit, Species DNA gyrase, subunit B [Mycobacterium tuberculosis] Target Mutant/Chimera Details

DNA gyrase, subunit B [Mycobacterium tuberculosis]:Wild

Target Species (Bioactivity)

Mycobacterium tuberculosis

Target Transfection

Non Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

29599928View in Reaxys

Substance Name

4-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-7-chloroquinoline

Measurement Parameter

IC50

Unit

μM

Quantitative value

1.82

Measurement pX

5.74

Target Name

DNA gyrase, subunit B [mycobacterium smegmatis ms155]

Target Synonyms

dna gyrase, subunit b

Target, Subunit, Species DNA gyrase, subunit B [mycobacterium smegmatis ms155] Target Mutant/Chimera Details

DNA gyrase, subunit B [mycobacterium smegmatis ms155]:Wild

Target Species (Bioactivity)

mycobacterium smegmatis ms155

Target Transfection

Transfected

Substance Action on Target

Inhibitor

180/378

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Bioassay Category

In Vitro (Efficacy)

Biological Species/NCBI Escherichia coli BL21 ID Substance RN

29599928View in Reaxys

Substance Name

4-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-7-chloroquinoline

Measurement Parameter

IC50

Unit

μM

Quantitative value

8.3

Measurement pX

5.08

Reaxys ID 28456685 View in Reaxys

91/181

Chemical Name: 3-((4-(2,3-dichlorophenyl)piperazin-1-yl)methyl)-5-fluoro-1H-indole Linear Structure Formula: C19H18Cl2FN3 Molecular Formula: C19H18Cl2FN3 Molecular Weight: 378.276 InChI Key: KRVNZLXHWSPXEE-UHFFFAOYSA-N Note:

Cl N N F HN

Substance Label (1) Label References 4

Druglikeness (1) 1 of 1

LogP

5.217

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

22.27

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

149 - 150

Location

supporting information

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

supporting information

181/378

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NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie International Edition; vol. 54; nb. 5; (2015); p. 1551 - 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys

Reaxys ID 18483400 View in Reaxys

92/181 CAS Registry Number: 1056000-42-0 Chemical Name: [3-(4-cyclobutyl-piperazin-1-ylmethyl)-1H-indol-5-yl]-piperidin-1-yl-methanone Linear Structure Formula: C23H32N4O Molecular Formula: C23H32N4O Molecular Weight: 380.533 InChI Key: XNTLEJQKHHOXOJ-UHFFFAOYSA-N Note:

N O

NH N

Substance Label (1) Label References Ex. 38

Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109333; (2008); (A1) English, View in Reaxys

Patent-Specific Data (1)

182/378

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References Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109333; (2008); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.836

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

42.58

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray Molecular peak ionisation); LCMS (Liquid chromatography mass spectrometry)

References Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109333; (2008); (A1) English, View in Reaxys

Medchem (2) 1 of 2

Target Name

Histamine H3 receptor [human]

Target Synonyms

g-protein coupled receptor 97; gpcr97; h3r; hh3r; histamine h3 receptor; hrh3

Target Uniprot ID

q9y5n1; q9y5n1-1; q9y5n1-2; q9y5n1-3; q9y5n1-4

Target, Subunit, Species Histamine H3 receptor [human]

2 of 2

Target Mutant/Chimera Details

Histamine H3 receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

SK-N-MC

Cell Fraction

Membrane

Substance RN

18483400View in Reaxys

Substance Name

ex38

Measurement Parameter

Unit

Quantitative value

427

Measurement pX

6.37

Concomitants: Compound RN

878384; 8975432

Concomitants: Compound name

Histamine; [3H]-Methylhistamine

Concomitants: Compound role

NSB; RAD

Target Name

Histamine H3 receptor [human]

Target Synonyms

g-protein coupled receptor 97; gpcr97; h3r; hh3r; histamine h3 receptor; hrh3

Target Uniprot ID

q9y5n1; q9y5n1-1; q9y5n1-2; q9y5n1-3; q9y5n1-4

183/378

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Target, Subunit, Species Histamine H3 receptor [human] Target Mutant/Chimera Details

Histamine H3 receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity of the compound towards human histamine H3 receptor expressed in SKN-MC cells using N-[3H]-alpha-methylhistamine (800 pM)

Biological Species/NCBI Human ID Cells/Cell Lines

SK-N-MC

Substance RN

18483400View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

427

Measurement pX

6.37

Concomitants: Compound name

[3H]N-alpha-methylhistamine

Concomitants: Compound role

RAD

Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109333; (2008); (A1) English, View in Reaxys

Reaxys ID 19332291 View in Reaxys

93/181

CAS Registry Number: 1166813-01-9 Linear Structure Formula: C19H19F2N7 Molecular Formula: C19H19F2N7 Molecular Weight: 383.404 InChI Key: YKSTVEVHSRIWRH-UHFFFAOYSA-N Note:

N N

F F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys Mass Spectrometry (1)

184/378

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Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Molecular peak

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332291View in Reaxys

Substance Name

265

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.8

Measurement pX

5.42

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

1e3g; 1gs4; 1t5z; 1t63; 1t65; 1xj7; 1xow; 1xq3; 1z95; 2am9; 2ama; 2amb; 2ao6; 2ax6; 2ax7; 2ax8; 2ax9; 2axa; 2hvc; 2oz7; 2pio; 2pip; 2piq; 2pir; 2pit; 2piu; 2piv; 2piw; 2pix; 2pkl; 2pnu; 2q7i; 2q7j; 2q7k; 2q7l; 2yhd; 2ylo; 2ylp; 2ylq; 2z4j; 3b5r; 3b65; 3b66; 3b67; 3b68; 3btr; 3l3x; 3l3z; 3rlj; 3rll; 3v49; 3v4a; 3zqt; 4hlw; 4k7a; 4oea; 4oed; 4oey; 4oez; 4ofr; 4ofu; 4ogh; 4oh5; 4oh6; 4oha; 4oil; 4oiu; 4oj9; 4ojb; 4ok1; 4okb; 4okt; 4okw; 4okx; 4olm

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound (dissolved in 100 DMSO) against down-regulation of human Androgen receptor level in LNCaP prostate cancer cell line upon incubation for 20-22 hours at 37 degree C

Cells/Cell Lines

LN-CAP

Substance RN

19332291View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

3.8

Measurement pX

5.42

Target Name

androgen receptor [Rattus norvegicus]

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Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332291View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 8798976 View in Reaxys

94/181 Linear Structure Formula: C20H18N4Cl2 Molecular Formula: C20H18Cl2N4 Molecular Weight: 385.296 Type of Substance: heterocyclic InChI Key: LLMBUJCYVGLEBH-UHFFFAOYSA-N Note:

N Cl

Substance Label (1) Label References 3c

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.779

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

174

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy)

186/378

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

360

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys Medchem (6) 1 of 6

Target Name

D(1A) dopamine receptor [taurine cattle]

Target Synonyms

d(1a) dopamine receptor; d1ar; dopamine d1 receptor; drd1

Target Uniprot ID

q95136

Target, Subunit, Species D(1A) dopamine receptor [taurine cattle] Target Mutant/Chimera Details

D(1A) dopamine receptor [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI taurine cattle ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

8798976View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

450

Deviation

Measurement pX

6.35

Concomitants: Compound RN

3620147; 1719757; 4154917; 1716295

187/378

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Concomitants: Compound name

[3H]-SCH 23390; Dithiothreitol; Butaclamol; EDTA

Concomitants: Compound role

RAD; COM; NSB; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 2 of 6

Target Name

Dopamine 2 long receptor [human]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [human] Target Mutant/Chimera Details

Dopamine 2 long receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8798976View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

790

Deviation

Measurement pX

6.1

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 3 of 6

Target Name

D(2) dopamine receptor (isoform Short) [human]

Target Synonyms

d(2) dopamine receptor (isoform short)

Target, Subunit, Species D(2) dopamine receptor (isoform Short) [human] Target Mutant/Chimera Details

D(2) dopamine receptor (isoform Short) [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

188/378

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Substance RN

8798976View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

480

Deviation

Measurement pX

6.32

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 4 of 6

Target Name

D(3) dopamine receptor [human]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p35462

Target PDB ID

3pbl

Target, Subunit, Species D(3) dopamine receptor [human] Target Mutant/Chimera Details

D(3) dopamine receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8798976View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

870

Deviation

140

Measurement pX

6.06

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

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Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 5 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8798976View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

Measurement Parameter

Unit

Quantitative value

Deviation

3.50000

Measurement pX

7.66

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys 6 of 6

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

8798976View in Reaxys

Substance Name

Substance Dose

0.0100000 nM

190/378

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Measurement Parameter

Quantitative value

1.1

Concomitants: Compound RN

632204; 331267; 1719757; 1716295

Concomitants: Compound name

[3H]-Spiperone; Haloperidol; Dithiothreitol; EDTA

Concomitants: Compound role

RAD; NSB; COM; COM

Huebner; Kraxner; Gmeiner; Journal of Medicinal Chemistry; vol. 43; nb. 23; (2000); p. 4563 - 4569, View in Reaxys

Reaxys ID 28456680 View in Reaxys

95/181 Chemical Name: 5-fluoro-3-((4-(2-methoxyphenyl)piperazin-1yl)methyl)-1H-indole formic acid salt Linear Structure Formula: C20H22FN3O*CH2O2 Molecular Formula: CH2O2*C20H22FN3O Molecular Weight: 385.438 InChI Key: CVQDWSOBERUNJM-UHFFFAOYSA-N Note:

HN O

F N

Substance Label (1) Label References 1

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.8

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

191/378

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Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert; Angewandte Chemie - International Edition; vol. 54; nb. 5; (2015); p. 1551 1555; Angew. Chem.; vol. 127; nb. 5; (2015); p. 1571 - 1575,5, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Reaxys ID 11725014 View in Reaxys

96/181 Chemical Name: 3-[4-(4-chloro-2,5-dimethoxyphenyl)piperazin-1-yl]methylindole Linear Structure Formula: C21H24ClN3O2 Molecular Formula: C21H24ClN3O2 Molecular Weight: 385.893 InChI Key: DWFKVFVRIJSCBL-UHFFFAOYSA-N Note:

N N NH

Cl O

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 8

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.264

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.73

Lipinski Number

Veber Number

Reaxys ID 25587847 View in Reaxys

97/181

192/378

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Linear Structure Formula: C21H30N4O3 Molecular Formula: C21H30N4O3 Molecular Weight: 386.494 InChI Key: UYQOFILLYJJDJD-UHFFFAOYSA-N Note:

H N

N O

Druglikeness (1) 1 of 1

LogP

1.889

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

88.67

Lipinski Number

Veber Number

Medchem (6) 1 of 6

Target Name

Histone deacetylase [human]

Target Synonyms

histone deacetylase

Target, Subunit, Species Histone deacetylase [human]

2 of 6

Target Mutant/Chimera Details

Histone deacetylase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Histone deacetylase in human HeLa extract upon incubation for 1 h at 37 degree C in 20 mM Tris, pH 7.4

Cells/Cell Lines

HeLa

Substance RN

25587847View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 1 [human]

Target Synonyms

hd1; hdac1; histone deacetylase 1; rpd3l1

Target Uniprot ID

q13547

Target PDB ID

4bkx

Target, Subunit, Species Histone deacetylase 1 [human] Target Mutant/Chimera Details

Histone deacetylase 1 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

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3 of 6

Bioassay Details

Inhibitory activity of the compound against human recombinant Histone deacetylase 1 transfected in to baculovirus infected SF9 cells upon incubation for 1 h at 37 degree C in 20 mM Tris, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587847View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 2 [Mus musculus]

Target Synonyms

hd2; hdac2; histone deacetylase 2; yy1 transcription factor-binding protein; yy1bp

Target Uniprot ID

p70288

Target, Subunit, Species Histone deacetylase 2 [Mus musculus]

4 of 6

Target Mutant/Chimera Details

Histone deacetylase 2 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against mouse recombinant Histone deacetylase 2 transfected in to baculovirus infected SF9 cells upon incubation for 1 h at 37 degree C in 20 mM Tris, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587847View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 1 [human]

Target Synonyms

hd1; hdac1; histone deacetylase 1; rpd3l1

Target Uniprot ID

q13547

Target PDB ID

4bkx

Target, Subunit, Species Histone deacetylase 1 [human] Target Mutant/Chimera Details

Histone deacetylase 1 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against recombinant full length human Histone deacetylase 1 expressed in Sf9 insect cells upon incubation at 37 degree C for 1 hr in 20 mM Tris buffer, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587847View in Reaxys

194/378

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5 of 6

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase 2 [Mus musculus]

Target Synonyms

hd2; hdac2; histone deacetylase 2; yy1 transcription factor-binding protein; yy1bp

Target Uniprot ID

p70288

Target, Subunit, Species Histone deacetylase 2 [Mus musculus]

6 of 6

Target Mutant/Chimera Details

Histone deacetylase 2 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against recombinant full length mouse Histone deacetylase 2 expressed in Sf9 insect cells upon incubation at 37 degree C for 1 hr in 20 mM Tris buffer, pH 7.4

Cells/Cell Lines

Sf9

Substance RN

25587847View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Histone deacetylase [human]

Target Synonyms

histone deacetylase

Target, Subunit, Species Histone deacetylase [human] Target Mutant/Chimera Details

Histone deacetylase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HeLa

Substance RN

25587847View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

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Reaxys ID 31231727 View in Reaxys

98/181

Chemical Name: N-[N-(3-indolylmethyl)-aminoethyl]-N-piperazinyl-3-indolylmethylamine Linear Structure Formula: C24H29N5 Molecular Formula: C24H29N5 Molecular Weight: 387.528 InChI Key: NPDSIOQSXZZAFX-UHFFFAOYSA-N Note:

N NH

Substance Label (1) Label References 19

Druglikeness (1) 1 of 1

LogP

2.956

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

50.09

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, TongHua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun; Journal of Asian Natural Products Research; vol. 19; nb. 6; (2017); p. 610 - 622, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry)

196/378

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electrospray ionisation (ESI); spectrum

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Medchem (4) 1 of 4

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231727View in Reaxys

Substance Name

N-[N-(3-indolylmethyl)-aminoethyl]-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

220.97

Target Name

Melatonin receptor type 1 [human]

Target Synonyms

melatonin receptor type 1

Target, Subunit, Species Melatonin receptor type 1 [human] Target Mutant/Chimera Details

Melatonin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231727View in Reaxys

Substance Name

N-[N-(3-indolylmethyl)-aminoethyl]-N-piperazinyl-3-indolylmethylamine

Substance Dose

0.02-1.52 mM

Measurement Parameter

EC50

197/378

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Unit

Quantitative value

0.39

Measurement pX

3.41

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231727View in Reaxys

Substance Name

N-[N-(3-indolylmethyl)-aminoethyl]-N-piperazinyl-3-indolylmethylamine

Substance Dose

1.00 mM

Measurement Parameter

Agonistic rate

Unit

Quantitative value

467.55

Target Name

5-hydroxytryptamine receptor 1a [human]

Target Synonyms

5-ht-1a; 5-ht1a; 5-hydroxytryptamine receptor 1a; adrb2rl1; adrbrl1; g-21; htr1a; serotonin receptor 1a

Target Uniprot ID

p08908

Target, Subunit, Species 5-hydroxytryptamine receptor 1a [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 1a [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

31231727View in Reaxys

Substance Name

N-[N-(3-indolylmethyl)-aminoethyl]-N-piperazinyl-3-indolylmethylamine

Substance Dose

0.02-1.52 mM

198/378

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Measurement Parameter

EC50

Unit

Quantitative value

0.46

Measurement pX

3.34

Reaxys ID 22705331 View in Reaxys

99/181 Linear Structure Formula: C18H18BrN3O2 Molecular Formula: C18H18BrN3O2 Molecular Weight: 388.264 InChI Key: KWSRXGSGJKPCNC-UHFFFAOYSA-N Note:

N O

N H

Substance Label (1) Label References 5

Druglikeness (1) 1 of 1

LogP

2.528

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

52.48

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR (300 MHz, CDCl3): δ 10.31 (s, 1H, NH), 7.90 (d, 1H, J4,6 = 1.8 H-4), 7.64 (dd, 1H, J4',2' = 0.6, J4',3' = 2.4 Hz, H-4'), 7.37 (d, 1H, J7,6 = 8.7 Hz, H-7), 7.32 (d, 1H, J2,CH2 = 2.1, H-2), 7.21 (dd, J6,4 = 2.1, J6,7 = 8.7 Hz, H-6), 6.91 (dd, 1H, J2',4' = 0.6, J2',3' = 3.3 Hz, H-2'), 6.53 (q, 1H, J3',2',5' = 1.8 Hz, H-4'), 3.70 (s, 6H, Aryl-CH2/H-3",5"), 2.49 (br.s, H-2",6")

Signals [ppm]

10.31; 7.9; 7.64; 7.37; 7.32; 7.21; 6.91; 6.53; 3.7; 2.49

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Kind of signal

s, 1H, NH; d, 1H, J&4,6% = 1.8 H-4; dd, 1H, J&4',2'% = 0.6, J&4',3'% = 2.4 Hz, H-4'; d, 1H, J&7,6% = 8.7 Hz, H-7; d, 1H, J&2%,CH2 = 2.1, H-2; dd, J&6,4% = 2.1, J&6,7% = 8.7 Hz, H-6; dd, 1H, J&2',4'% = 0.6, J&2',3'% = 3.3 Hz, H-2'; q, 1H, J&3',2',5'% = 1.8 Hz, H-4'; s, 6H, Aryl-CH&2%/H-3",5"; br.s, H-2",6"

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Original Text (IR Spectroscopy)

IR (KBr): νmax 3062, 2922, 1603 cm-1;

Signals [cm-1]

3062; 2922; 1603

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Intensity [%]

387 m/z; 193 m/z; 30; 93; 62; 100 138 m/z; 95 m/z

EI (Electron impact); Spectrum

References Mesaik, M. Ahmed; Khan, Khalid Mohammed; Rahim, Fazal; Taha, Muhammad; Haider, Syed Moazzam; Perveen, Shahnaz; Khalid, Ahmed Shukralla; Abdalla, Omer M.; Soomro, Samreen; Voelter, Wolfgang; Bioorganic Chemistry; vol. 60; (2015); p. 118 122, View in Reaxys Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 283 VIS) [nm] Log epsilon

4.2

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View in Reaxys; Mesaik, M. Ahmed; Khan, Khalid Mohammed; Rahim, Fazal; Taha, Muhammad; Haider, Syed Moazzam; Perveen, Shahnaz; Khalid, Ahmed Shukralla; Abdalla, Omer M.; Soomro, Samreen; Voelter, Wolfgang; Bioorganic Chemistry; vol. 60; (2015); p. 118 - 122, View in Reaxys

Reaxys ID 27144079 View in Reaxys

100/181 CAS Registry Number: 355823-76-6 Linear Structure Formula: C23H29N3O3 Molecular Formula: C23H29N3O3 Molecular Weight: 395.502 InChI Key: QXQHDEHOKNWVNF-UHFFFAOYSA-N Note:

O NH

N N

O O

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 10

Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; STOJANOVIC, Milan; KATZ, Francine; LANDRY, Donald, W.; WO2014/113495; (2014); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.711

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.96

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

Cholinesterase

Target Synonyms

acylcholine acylhydrolase (cholinesterase); anticholineesterase; bche (cholinesterase); benzoylcholinesterase; btchoease; butyrylcholine esterase; butyrylcholinesterase; che1 (cholinesterase); choline esterase; choline esterase ii; choline esterase ii (unspecific); cholinesterase; eq-bche; non-specific cholinesterase; propionylcholinesterase; pseudocholinesterase

Target, Subunit, Species Cholinesterase

2 of 2

Target Mutant/Chimera Details

Cholinesterase:Wild

Substance Action on Target

Activator

Substance Effect

activation

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Ability of the compound towards activation of butyrylcholinesterase

Substance RN

27144079View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Reported

Target Name

acetylcholinesterase

Target Synonyms

ace (acetylcholinesterase); ace-1 (acetylcholinesterase); ace1 (acetylcholinesterase); acetyl.beta-methylcholinesterase; acetylcholine acetylhydrolase; acetylcholine hydrolase; acetylcholinesterase; acetylthiocholinesterase; ache (acetylcholinesterase); ache1; agap001356; cg17907; choline esterase i; true cholinesterase

Target, Subunit, Species acetylcholinesterase

201/378

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Target Mutant/Chimera Details

acetylcholinesterase:Wild

Substance Action on Target

Activator

Substance Effect

activation

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Ability of the compound towards activation of acetylcholinesterase

Substance RN

27144079View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Reported

Reaxys ID 31173349 View in Reaxys

101/181 Linear Structure Formula: C23H29N3O3 Molecular Formula: C23H29N3O3 Molecular Weight: 395.502 InChI Key: SKTMFTDDYHSSIN-UHFFFAOYSA-N Note:

N N

O O

Substance Label (1) Label References Compound 67

Maretzky, Thorsten; Swendeman, Steven; Mogollon, Elin; Weskamp, Gisela; Sahin, Umut; Reiss, Karina; Blobel, Carl P.; Biochemical Journal; vol. 474; nb. 9; (2017); p. 1469 - 1479, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.711

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.96

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

Disintegrin and metalloproteinase domain-containing protein 9

Target Synonyms

adam 9; adam9; cellular disintegrin-related protein; disintegrin and metalloproteinase domain-containing protein 9; kiaa0021; mcmp; mdc9; meltrin-gamma; metalloprotease/disintegrin/cysteine-rich protein 9; mltng; myeloma cell metalloproteinase

Target, Subunit, Species Disintegrin and metalloproteinase domain-containing protein 9 Target Mutant/Chimera Details

Disintegrin and metalloproteinase domain-containing protein 9:Wild

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

202/378

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Biological Species/NCBI Mus musculus ID Cells/Cell Lines

Embryonic fibroblast cell

Substance RN

31173349View in Reaxys

Substance Dose

1 - 5 μM

Measurement Parameter

% Inhibition

Measurement Object

of EphB4 shedding

Qualitative value

Active

Measurement pX

Maretzky, Thorsten; Swendeman, Steven; Mogollon, Elin; Weskamp, Gisela; Sahin, Umut; Reiss, Karina; Blobel, Carl P.; Biochemical Journal; vol. 474; nb. 9; (2017); p. 1469 - 1479, View in Reaxys 2 of 3

Target Name

Disintegrin and metalloproteinase domain-containing protein 10 [Mus musculus]

Target Synonyms

adam 10; adam10; disintegrin and metalloproteinase domain-containing protein 10; kuz; kuzbanian protein homolog; madm (disintegrin and metalloproteinase domain-containing protein 10); mammalian disintegrin-metalloprotease

Target Uniprot ID

o35598

Target, Subunit, Species Disintegrin and metalloproteinase domain-containing protein 10 [Mus musculus] Target Mutant/Chimera Details

Disintegrin and metalloproteinase domain-containing protein 10 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Target Transfection

Non Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

Embryonic fibroblast cell

Substance RN

31173349View in Reaxys

Substance Dose

1 - 5 μM

Measurement Parameter

% Inhibition

Measurement Object

BTC-AP shedding

Qualitative value

Not active

Measurement pX

Concomitants: Compound RN

3642126

Concomitants: Compound name

ionomycin

Concomitants: Compound role

STI

Target Name

Disintegrin and metalloproteinase domain-containing protein 17 [Mus musculus]

Target Synonyms

adam 17; adam17; disintegrin and metalloproteinase domain-containing protein 17; tace; tnf-alpha convertase; tnf-alpha-converting enzyme

Target Uniprot ID

q9z0f8

203/378

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Target, Subunit, Species Disintegrin and metalloproteinase domain-containing protein 17 [Mus musculus] Target Mutant/Chimera Details

Disintegrin and metalloproteinase domain-containing protein 17 [Mus musculus]:Wild

Target Species (Bioactivity)

Mus musculus

Target Transfection

Non Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

Embryonic fibroblast cell

Substance RN

31173349View in Reaxys

Substance Dose

1 - 5 μM

Measurement Parameter

% Inhibition

Measurement Object

TNF alpha-AP shedding

Qualitative value

Not active

Measurement pX

Concomitants: Compound RN

2407201

Concomitants: Compound name

phorbol 12-myristate 13-acetate

Concomitants: Compound role

STI

Maretzky, Thorsten; Swendeman, Steven; Mogollon, Elin; Weskamp, Gisela; Sahin, Umut; Reiss, Karina; Blobel, Carl P.; Biochemical Journal; vol. 474; nb. 9; (2017); p. 1469 - 1479, View in Reaxys

Reaxys ID 12317637 View in Reaxys

O N

Linear Structure Formula: C20H24N6O3 Molecular Formula: C20H24N6O3 Molecular Weight: 396.449 InChI Key: FEWWLHCFEBYWGW-UHFFFAOYSA-N Note:

N O

102/181

Patent-Specific Data (1) References Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (2005); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.606

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

95.14

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

156 - 158.6

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Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (2005); (A1) English, View in Reaxys

Reaxys ID 14173459 View in Reaxys

103/181

H N HN

CAS Registry Number: 528860-17-5 Chemical Name: [41] N-[3-(4-methylpiperazin-1-yl)methyl-1Hindol-5-yl]-α-toluenesulphonamide; N-[3-(4-methylpiperazin-1yl)methyl-1H-indol-5-yl]-α-toluenesulphonamide; N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-α-toluenesulphonamide Linear Structure Formula: C21H26N4O2S Molecular Formula: C21H26N4O2S Molecular Weight: 398.529 InChI Key: IOJVMOAYKYBHST-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 41

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys

Patent-Specific Data (2) Location in Patent References Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys Claim

Patent; Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi; US2003/191124; (2003); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.209

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

76.82

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

99 - 102

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys; Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

δ 2.11(s, 3H); 2.32(m, 6H); 3.35(m, 2H); 3.56(s, 2H); 4.29(s, 2H); 6.98(d, J=8.2 Hz 1H); 7.29(m, 7H); 7.53(s, 1H); 9.40(s, 1H) 10.94(s, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

205/378

2017-11-11 00:22:14

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Comment (NMR Spectroscopy)

Signals given

Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys IR Spectroscopy (2) 1 of 2

Original Text (IR Spectroscopy)

3398, 2934, 2806, 1458, 1331, 1284, 1153, 1127, 700, 542 1/cm

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 2 of 2

Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys

Medchem (8) 1 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro binding activity of the compound towards human 5-hydroxytryptamine 6 receptor transfected into HEK-293 cells using 2.7 nM [3H]-LSD as radioligand upon incubation at 37 degree C for 60 min in 50 mM Tris-HCl buffer, pH 7.4

Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Patent; Laboratorios del Dr. Esteve S.A.; EP2018861; (2009); (A1) English, View in Reaxys 2 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

206/378

2017-11-11 00:22:14

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against human 5-hydroxytryptamine 6 receptor expressing HEK 293 cell line using [3H]-LSD as radioligand incubated at 37 degree C for 60 minutes

Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Measurement Parameter

Activity

Qualitative value

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 3 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

4 of 8

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Antagonist

Substance Effect

antagonistic activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Antagonistic activity of the compound towards human 5-Hydroxytryptamine 6 receptor expressed in HEK 293 cells using [3H]-LSD (2.7nM) as radioligand

Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

207/378

2017-11-11 00:22:14

Bioassay Details

Inhibitory activity against human 5-hydroxytryptamine 6 receptor expressed in HEK 293 cell line using [3-H]-LSD (2.7 nM) as radioligand upon incubation at 37 degree C for 60 min in Tris-HCl buffer at 10 E-6 M concentration

Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi; US2003/191124; (2003); (A1) English, View in Reaxys 5 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

6 of 8

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against human recombinant 5-hydroxytryptamine 6 receptor expressed in HEK-293 cell line upon incubation with 50 mM Tris-HCl, pH 7.4 for 60 min at 37 degree C using non-linear regression analysis using the program EBDA/LIGAND

Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against human recombinant 5-hydroxytryptamine 6 receptor expressed in HEK 293 cell line using radioligand [3H]LSD upon incubation with 50 mM Tris-HCl, pH 7.4 for 60 min at 37 degree C

Cells/Cell Lines

HEK 293

208/378

2017-11-11 00:22:14

7 of 8

Substance RN

14173459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

8 of 8

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against human recombinant 5-hydroxytryptamine 6 receptor expressed in HEK-293 cells using [3H]-LSD as radioligand upon incubation for 60 min at 37 degree C in 50 mM Tris-HCl (pH 7.4)

Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding activity towards human 5-hydroxytryptamine 6 receptor expressed in HEK 293 cells using 2.7 nM [3H]-LSD as radioligand upon incubation in 50 mM Tris HCl buffer, pH 7.4 at 37 degree C for 60 min

Cells/Cell Lines

HEK 293

Substance RN

14173459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

209/378

2017-11-11 00:22:14

Reaxys ID 11951128 View in Reaxys

104/181 CAS Registry Number: 701205-16-5 Chemical Name: 5-bromo-3-(4-(1-methoxyphen-2-yl)piperazin-1-ylmethyl)-1H-indole Linear Structure Formula: C20H22BrN3O Molecular Formula: C20H22BrN3O Molecular Weight: 400.318 InChI Key: FSGUUQJMURQGAW-UHFFFAOYSA-N Note:

N Br

O NH

Substance Label (1) Label References D 158

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.525

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 22705332 View in Reaxys

105/181

Chemical Name: 5-bromo-3-{[4-(4-methoxyphenyl)-1-piperazinyl]methyl}-1H-indole Linear Structure Formula: C20H22BrN3O Molecular Formula: C20H22BrN3O Molecular Weight: 400.318 InChI Key: BYIWJSNUXJJKNX-UHFFFAOYSA-N Note:

N H

Druglikeness (1) 1 of 1

LogP

4.525

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

31.5

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

210/378

2017-11-11 00:22:14

Solvents (NMR Spectro- hexadeuterioacetone scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz; Journal of the Chemical Society of Pakistan; vol. 34; nb. 3; (2012); p. 748 - 757, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 282 VIS) [nm] Log epsilon

4.2

Reaxys ID 24428086 View in Reaxys N

106/181 Linear Structure Formula: C20H19F3N6 Molecular Formula: C20H19F3N6 Molecular Weight: 400.406 Note:

N N

F F

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

24428086View in Reaxys

Substance Name

807

Measurement Parameter

IC50

Unit

µM

Quantitative value

7.5

Measurement pX

5.12

211/378

2017-11-11 00:22:14

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

24428086View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

7.5

Measurement pX

5.12

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

24428086View in Reaxys

Qualitative Results

Not Published

212/378

2017-11-11 00:22:14

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 19332396 View in Reaxys

107/181

CAS Registry Number: 1166813-33-7 Linear Structure Formula: C19H18F3N7 Molecular Formula: C19H18F3N7 Molecular Weight: 401.394 InChI Key: GPTAPLOYDQZRFX-UHFFFAOYSA-N Note:

F F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332396View in Reaxys

Substance Name

290

Measurement Parameter

IC50

Unit

µM

Quantitative value

5.8

Measurement pX

5.24

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

213/378

2017-11-11 00:22:14

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332396View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

5.8

Measurement pX

5.24

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332396View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

214/378

2017-11-11 00:22:14

Reaxys ID 19332422 View in Reaxys

108/181 CAS Registry Number: 1166811-03-5 Chemical Name: 6-[4-(1H-indol-3-ylmethyl)piperazin-1-yl]-3(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine Linear Structure Formula: C19H18F3N7 Molecular Formula: C19H18F3N7 Molecular Weight: 401.394 InChI Key: YHGQQKFBDVHQFM-UHFFFAOYSA-N Note:

N HN

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300.132

Original Text (NMR Spectroscopy)

1H NMR (300.132 MHz, DMSO-d6) δ 2.51-2.59 (4H, m), 3.54-3.65 (4H, m), 3.71 (2H, s), 6.95-7.03 (IH, m), 7.04-7.12 (IH, m), 7.26 (IH, d), 7.36 (IH, d), 7.56 (IH, d), 7.66 (IH, d), 8.22 (IH, d), 10.94 (IH, s) (Signal at 2.5 partially obscured by DMSO);

Comment (NMR Spectroscopy)

Signals given

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (4) 1 of 4

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332422View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.93

Measurement pX

6.03

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 4

Target Name

androgen receptor [Rattus norvegicus];+androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4 + androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207 + p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w + 1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus]

215/378

2017-11-11 00:22:14

Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild + androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Substance RN

19332422View in Reaxys

Substance Name

Substance Dose

1.00000E-08 M

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound name

Fluormone AL Red

Concomitants: Compound role

RAD

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 3 of 4

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human] Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332422View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.93

216/378

2017-11-11 00:22:14

4 of 4

Measurement pX

6.03

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332422View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Reaxys ID 20623266 View in Reaxys

109/181 CAS Registry Number: 1240299-43-7 Chemical Name: 6-[4-(1H-indol-3-ylmethyl)piperazin-1-yl]-3(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine Linear Structure Formula: C19H20F3N7 Molecular Formula: C19H20F3N7 Molecular Weight: 403.41 InChI Key: AUBNKPBCVWTIIG-UHFFFAOYSA-N Note:

N N F

Substance Label (1) Label References 11

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; WO2010/92371; (2010); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.921

H Bond Donors

H Bond Acceptors

Rotatable Bonds

217/378

2017-11-11 00:22:14

TPSA

65.34

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Location

Page/Page column 103

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; WO2010/92371; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry)

Page/Page column 103

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; WO2010/92371; (2010); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

20623266View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

8.6

Measurement pX

5.07

Concomitants: Compound RN

24140449; 1723797

Concomitants: Compound name

Penicillin-Streptomycin; Glutamine

Concomitants: Compound role

VPR; VPR

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : measured level of androgen receptor (AR) number; reducing of Biological AssaysThe ability of compounds to reduce Androgen Receptor (AR) numbers was assessed in a cell based immuno-fluorescence assay using the LNCaP prostate epithelial cell line. a) LNCaP Androgen Receptor down-regulation cell assayThis immunofluorescence end point assay measures the ability of

Cells/Cell Lines

LNCaP clone FGC

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Substance RN

20623266View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

8.6

Measurement pX

5.07

Patent; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; (181 pag.); WO2010/92371; (A1); (2010), View in Reaxys 3 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Cells/Cell Lines

LNCaP clone FGC

Substance RN

20623266View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

8.6

Measurement pX

5.07

Patent; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; (181 pag.); WO2010/92371; (A1); (2010), View in Reaxys

Reaxys ID 11725015 View in Reaxys

110/181 O

Chemical Name: 5-methanesulfonyl-3-[4-(4-chlorophenyl)piperazin-1-yl]methylindole Linear Structure Formula: C20H22ClN3O2S Molecular Formula: C20H22ClN3O2S Molecular Weight: 403.933 InChI Key: RLQSXVIABFBZGJ-UHFFFAOYSA-N Note:

O S

N N NH

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 8

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.955

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

64.79

Lipinski Number

Veber Number

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Reaxys ID 19332444 View in Reaxys

111/181

CAS Registry Number: 1166813-28-0 Linear Structure Formula: C20H18F2N8 Molecular Formula: C20H18F2N8 Molecular Weight: 408.413 InChI Key: VHGCZEIQFHAMMD-UHFFFAOYSA-N Note:

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332444View in Reaxys

Substance Name

286

Measurement Parameter

IC50

Unit

µM

Quantitative value

8.5

Measurement pX

5.07

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

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3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332444View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

8.5

Measurement pX

5.07

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332444View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 14173860 View in Reaxys

112/181

221/378

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O N

CAS Registry Number: 528860-05-1 Chemical Name: N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-trans-β-styrenesulphonamide; N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-trans-β-styrenesulphonamide; N[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-trans-3-styrenesulphonamide Linear Structure Formula: C22H26N4O2S Molecular Formula: C22H26N4O2S Molecular Weight: 410.54 InChI Key: JYFZTHMGIJASIF-NTEUORMPSA-N Note:

S NH

Substance Label (1) Label References 37

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.819

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

76.82

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

203

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

δ 2.06(s, 3H); 2.22(m, 6H); 3.36(m 2H); 3.4 (s, 2H); 6.95(dd, J=8.6, 1.8 Hz, 1H); 7.18( 2H); 7.24(m, 2H); 7.37(m, 3H); 7.45(d, J=1.8 Hz, 1H); 7.61(m, 2H); 9.53(s 1H); 10.90(s, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Comment (NMR Spectroscopy)

Signals given

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Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys IR Spectroscopy (2) 1 of 2

Original Text (IR Spectroscopy)

2809, 1340, 1150, 746, 542 1/cm

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 2 of 2

Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys

Medchem (11) 1 of 11

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Patent; Laboratorios del Dr. Esteve S.A.; EP2018861; (2009); (A1) English, View in Reaxys 2 of 11

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against HEK-293 cell membranes expressing human 5hydroxytryptamine 6 receptor using [3H]-LSD (2.7 nM) as radioligand upon incubation in 50 mM Tris-HCl, pH 7.4 at 37 degree C for 60 min

Biological Species/NCBI Human ID

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3 of 11

Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Target Name

Neuropeptide Y receptor type 1 [Rattus norvegicus]; Neuropeptide Y receptor type 2 [Rattus norvegicus]

Target Synonyms

fc5; neuropeptide y receptor type 1; npy1-r; npy1r + neuropeptide y receptor type 2

Target Uniprot ID

p21555

Target, Subunit, Species Neuropeptide Y receptor type 1 [Rattus norvegicus]; Neuropeptide Y receptor type 2 [Rattus norvegicus] Target Mutant/Chimera Details

Neuropeptide Y receptor type 1 [Rattus norvegicus]:Wild; Neuropeptide Y receptor type 2 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus; Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against neuropeptide Y receptor type 1 in rat hippocampus using [125I][Leu31,Pro34]YY as radioligand

Biological Species/NCBI Rattus norvegicus ID

4 of 11

Substance RN

14173860View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

Pro34 YY; [125I]Leu31

Concomitants: Compound role

RAD; RAD

Target Name

Neuropeptide Y receptor type 5 [Rattus norvegicus]

Target Synonyms

neuropeptide y receptor type 5; npy-y5 receptor; npy5-r; npy5r; npyr5; npyy5-r; y5 receptor

Target Uniprot ID

q63634

Target, Subunit, Species Neuropeptide Y receptor type 5 [Rattus norvegicus] Target Mutant/Chimera Details

Neuropeptide Y receptor type 5 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against C6 cells transfected with rat neuropeptide Y5receptor using 100 pM [125I]-PYY (100pM) as radioligand upon incubation in 25 mM TrisHCl, pH 7.4 for 2 hrs at 25 degree C

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Biological Species/NCBI Rattus norvegicus ID

5 of 11

Cells/Cell Lines

Substance RN

14173860View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[125I]Peptide YY

Concomitants: Compound role

RAD

Target Name

Neuropeptide Y receptor type 1 [Rattus norvegicus]; Neuropeptide Y receptor type 2 [Rattus norvegicus]

Target Synonyms

fc5; neuropeptide y receptor type 1; npy1-r; npy1r + neuropeptide y receptor type 2

Target Uniprot ID

p21555

Target, Subunit, Species Neuropeptide Y receptor type 1 [Rattus norvegicus]; Neuropeptide Y receptor type 2 [Rattus norvegicus] Target Mutant/Chimera Details

Neuropeptide Y receptor type 1 [Rattus norvegicus]:Wild; Neuropeptide Y receptor type 2 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus; Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against neuropeptide Y receptor type 2 in rat hippocampus using [125I]-PYY3-36 (28 pM) as radioligand incubated for 150 min at 25 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID

6 of 11

Substance RN

14173860View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Concomitants: Compound name

[125I]Peptide YY (3-36)

Concomitants: Compound role

RAD

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against human 5-hydroxytryptamine 6 receptor expressing HEK 293 cell line using [3H]-LSD as radioligand incubated at 37 degree C for 60 minutes

225/378

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Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Measurement Parameter

Activity

Qualitative value

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 7 of 11

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

8 of 11

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Antagonist

Substance Effect

antagonistic activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Antagonistic activity of the compound towards human 5-Hydroxytryptamine 6 receptor expressed in HEK 293 cells using [3H]-LSD (2.7nM) as radioligand

Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

226/378

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Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi; US2003/191124; (2003); (A1) English, View in Reaxys 9 of 11

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

10 of 11

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Qualitative Results

Not Published

227/378

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11 of 11

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14173860View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 25292007 View in Reaxys HN

113/181 Linear Structure Formula: C22H26N4O2S Molecular Formula: C22H26N4O2S Molecular Weight: 410.54 InChI Key: XKJTZDFTSAZUEV-UHFFFAOYSA-N Note:

O N H

S O

Druglikeness (1) 1 of 1

LogP

2.687

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

76.82

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

5-hydroxytryptamine receptor 6 [Rattus norvegicus]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6; st-b17

Target Uniprot ID

p31388

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [Rattus norvegicus]:Wild

228/378

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Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding activity of the compound towards 5-hydroxytryptamine (serotonin) receptor 6 was determined in rat room temperature

Biological Species/NCBI Rattus norvegicus ID Substance RN

25292007View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Laboratorios del Dr. Esteve S.A.; EP2020230; (2009); (A1) English, View in Reaxys 2 of 2

Target Name

5-Hydroxytryptamine 6 receptor

Target Synonyms

5-hydroxytryptamine 6 receptor

Target, Subunit, Species 5-Hydroxytryptamine 6 receptor Target Mutant/Chimera Details

5-Hydroxytryptamine 6 receptor:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against 5-hydroxytryptamine (serotonin) receptor 6 was determined

Substance RN

25292007View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Laboratorios del Dr. Esteve S.A.; EP2020230; (2009); (A1) English, View in Reaxys

Reaxys ID 15337111 View in Reaxys

114/181 CAS Registry Number: 350850-00-9 Chemical Name: 1-[(4-Cyano-5-methyl-4-phenyl)hexyl]-4-[(3indolyl)methyl]piperazine Linear Structure Formula: C27H34N4 Molecular Formula: C27H34N4 Molecular Weight: 414.594 InChI Key: AYCOHRNAXUGXCP-UHFFFAOYSA-N Note:

N HN

Druglikeness (1) 1 of 1

LogP

5.168

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.06

Lipinski Number

Veber Number

229/378

2017-11-11 00:22:14

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR (400MHz, CDCl ) δ 0.76 (d, J = 6.8Hz, 3H), 1.04-1.18 (m, 1H), 1.18 (d, J = 3 6.8Hz, 3H), 1.47-1.60 (m, 1H), 1.86 (dt, J = 4.4Hz, J = 12.4Hz, 1H), 2.03-2.16 (m, 2H), 2.22-2.32 (m, 2H), 2.33 (bs, 4H), 2.49 (bs, 4H), 3.70 (s, 2H), 7.05-7.20 (m, 4H), 7.23-7.48 (m, 5H), 7.70 (d, J = 6.8Hz, 1H), 8.25-8.40 (m, 1H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

0.76; 1.04 - 1.18; 1.18; 1.47 - 1.6; 1.86; 2.03 - 2.16; 2.22 - 2.32; 2.33; 2.49; 3.7; 7.05 - 7.2; 7.23 - 7.48; 7.7; 8.25 - 8.4

Kind of signal

d, J = 6.8Hz, 3H; m, 1H; d, J = 6.8Hz, 3H; m, 1H; dt, J = 4.4Hz, J = 12.4Hz, 1H; m, 2H; m, 2H; bs, 4H; bs, 4H; s, 2H; m, 4H; m, 5H; d, J = 6.8Hz, 1H; m, 1H

Patent; Eisai Co., Ltd.; EP1254895; (2002); (A1) English, View in Reaxys Medchem (1) 1 of 1

Target Name

Voltage-dependent P/Q-type calcium channel [Rattus norvegicus]; Voltage-dependent Ntype calcium channel [Rattus norvegicus]

Target Synonyms

voltage-dependent p/q-type calcium channel + voltage-dependent n-type calcium channel

Target, Subunit, Species Voltage-dependent P/Q-type calcium channel [Rattus norvegicus]; Voltage-dependent Ntype calcium channel [Rattus norvegicus] Target Mutant/Chimera Details

Voltage-dependent P/Q-type calcium channel [Rattus norvegicus]:Wild; Voltage-dependent N-type calcium channel [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus; Rattus norvegicus

Target Transfection

Non Transfected; Non Transfected

Substance Action on Target

Blocker

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Flux uptake

Biological Species/NCBI Rattus norvegicus ID Organs/Tissues

brain cortex

Cell Fraction

Synaptosome

Substance RN

15337111View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

7.6

Measurement pX

5.12

Concomitants: Compound RN

8183748; 4241647; 8137362

Concomitants: Compound name

[Fura-2/AM]; Ca2+; KCl

Concomitants: Compound role

MAR; SUB; IND

230/378

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Patent; Eisai Co., Ltd.; EP1254895; (2002); (A1) English, View in Reaxys

Reaxys ID 25120862 View in Reaxys

115/181 Linear Structure Formula: C24H22FN5O Molecular Formula: C24H22FN5O Molecular Weight: 415.47 InChI Key: BAEVARPPYYAVPQ-UHFFFAOYSA-N Note:

HN F O N

Druglikeness (1) 1 of 1

LogP

2.834

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

78.92

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

5-Hydroxytryptamine 2A receptor

Target Synonyms

5-ht-2; 5-ht-2a; 5-ht2a; 5-htr2a; 5-hydroxytryptamine 2a receptor; 5-hydroxytryptamine receptor; 5-hydroxytryptamine receptor 2a (5-hydroxytryptamine 2a receptor); 5htr2a; egm_08468; htr2 (5-hydroxytryptamine 2a receptor); htr2a; serotonin receptor 2a (5-hydroxytryptamine 2a receptor)

Target, Subunit, Species 5-Hydroxytryptamine 2A receptor

2 of 3

Target Mutant/Chimera Details

5-Hydroxytryptamine 2A receptor:Wild

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro affinity of the compound towards 5-hydroxytryptamine 2A receptor

Substance RN

25120862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Sodium-dependent serotonin transporter

Target Synonyms

5ht transporter; 5htt; cg4545; cocaine-sensitive serotonin transporter; dsert1; htt (sodiumdependent serotonin transporter); sert; slc6a4; sodium-dependent serotonin transporter; solute carrier family 6 member 4

Target, Subunit, Species Sodium-dependent serotonin transporter Target Mutant/Chimera Details

Sodium-dependent serotonin transporter:Wild

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

231/378

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3 of 3

Bioassay Details

In vitro affinity of the compound towards serotonin transporter

Substance RN

25120862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-Hydroxytryptamine 1A receptor

Target Synonyms

5-ht receptor 2a; 5-ht-1a; 5-ht1a; 5-hydroxytryptamine 1a receptor; 5-hydroxytryptamine receptor 1a; 5-hydroxytryptamine receptor 2a (5-hydroxytryptamine 1a receptor); 5ht-r2a; 5ht1a; adrb2rl1; adrbrl1; cg16720; g-21; gpcr18; htr1a; serotonin receptor 1a; serotonin receptor 2a (5-hydroxytryptamine 1a receptor); x5-ht1a

Target, Subunit, Species 5-Hydroxytryptamine 1A receptor Target Mutant/Chimera Details

5-Hydroxytryptamine 1A receptor:Wild

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro affinity of the compound towards 5-hydroxytryptamine 1A receptor using [3H]5-methoxy-3-(di-n-propylamino)chroman as radioligand

Substance RN

25120862View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 29891289 View in Reaxys

116/181

Linear Structure Formula: C25H25FN4O Molecular Formula: C25H25FN4O Molecular Weight: 416.498 InChI Key: DPIIFXNAGCUCFF-UHFFFAOYSA-N Note:

N HN

F N H

Substance Label (1) Label References 86

Patent; Institut Pasteur Korea; Qurient Co. Ltd.; Kim, Chae Seung; Kang, Seon Hui; Lee, Se Yeon; So, Min Jeong; So, Moo Yeong; Seo, Cheong Jae; Lee, Soo MI; Kim, Jun Won; Song, Ri Ta; Oh, Sang Mi; Cho, Soo Yeong; Kwon, Cheong Jin; Gong, Seon Joo; Ryu, Ji Yeong; Kim, Seong Bom; Park, Eun Jeong; Han, Song Jun; Kim, Cheong Hwan; Lee, Sang Cheol; Choi, Ka Hui; Lee, Yun Mi; Nam, Ki Yeon; (47 pag.); KR2016/9750; (2016); (A) Korean, View in Reaxys

Patent-Specific Data (1) References Patent; Institut Pasteur Korea; Qurient Co. Ltd.; Kim, Chae Seung; Kang, Seon Hui; Lee, Se Yeon; So, Min Jeong; So, Moo Yeong; Seo, Cheong Jae; Lee, Soo MI; Kim, Jun Won; Song, Ri Ta; Oh, Sang Mi; Cho, Soo Yeong; Kwon, Cheong Jin; Gong, Seon Joo; Ryu, Ji Yeong; Kim, Seong Bom; Park, Eun Jeong; Han, Song Jun; Kim, Cheong Hwan; Lee, Sang Cheol; Choi, Ka Hui; Lee, Yun Mi; Nam, Ki Yeon; (47 pag.); KR2016/9750; (2016); (A) Korean, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.779

H Bond Donors

232/378

2017-11-11 00:22:14

H Bond Acceptors

Rotatable Bonds

TPSA

54.53

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties orange

References

Paragraph 0195

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

Paragraph 0195

References

liquid chromatog- Paragraph 0195 raphy mass spectrometry (LCMS); electrospray ionisation (ESI); spectrum

Reaxys ID 25209760 View in Reaxys

117/181

O N

Linear Structure Formula: C25H31N5O Molecular Formula: C25H31N5O Molecular Weight: 417.554 InChI Key: JHVLNPHVAJOJTR-UHFFFAOYSA-N Note:

N HN

Druglikeness (1) 1 of 1

LogP

1.83

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.47

233/378

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Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

Histamine H3 receptor [guinea pig]

Target Synonyms

histamine h3 receptor

Target, Subunit, Species Histamine H3 receptor [guinea pig]

2 of 2

Target Mutant/Chimera Details

Histamine H3 receptor [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity towards histamine H3 receptor of guinea pig brain using 3 nM [3H]RAMH or [3H]NAMH upon incubation with 50 mM Tris buffer, pH 7.5 at 30 degree C for 30 min with the compound dissolved in DMSO; Range = 0.2 - 600 nM

Organs/Tissues

brain tissue

Substance RN

25209760View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

600

Measurement pX

6.22

Target Name

Histamine H3 receptor [guinea pig]

Target Synonyms

histamine h3 receptor

Target, Subunit, Species Histamine H3 receptor [guinea pig] Target Mutant/Chimera Details

Histamine H3 receptor [guinea pig]:Wild

Target Species (Bioactivity)

guinea pig

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity towards Histamine H3 receptor from guinea pig brain using [3H]R-alphamethyl histamine (3 nM) as radioligand upon incubation at 30 degree C for 30 min in 50 mM Tris buffer, pH 7.5 with the compound dissolved in DMSO; Range = 0.2 - 600 nM

Organs/Tissues

brain

Substance RN

25209760View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

600

Measurement pX

6.22

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Reaxys ID 19332392 View in Reaxys

118/181

CAS Registry Number: 1166813-29-1 Linear Structure Formula: C19H18ClF2N7 Molecular Formula: C19H18ClF2N7 Molecular Weight: 417.849 InChI Key: QXIKGVSTVMMSLI-UHFFFAOYSA-N Note:

Cl F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332392View in Reaxys

Substance Name

287

Measurement Parameter

IC50

Unit

µM

Quantitative value

Measurement pX

5.7

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

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3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332392View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

5.7

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332392View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 24428089 View in Reaxys

119/181

236/378

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Linear Structure Formula: C20H18F4N6 Molecular Formula: C20H18F4N6 Molecular Weight: 418.397 Note:

N N

F F

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

24428089View in Reaxys

Substance Name

808

Measurement Parameter

IC50

Unit

µM

Quantitative value

Measurement pX

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

24428089View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Target Name

androgen receptor [Rattus norvegicus]

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Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

24428089View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 11725016 View in Reaxys

120/181 O

Chemical Name: N-methyl-3-[4-(4-chlorophenyl)piperazin-1-ylmethyl]-5-indolesulfonamide Linear Structure Formula: C20H23ClN4O2S Molecular Formula: C20H23ClN4O2S Molecular Weight: 418.947 InChI Key: QCPPIIFNZUDTSX-UHFFFAOYSA-N Note:

O S

N H

N N NH

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 8

Patent; Neugen Pharma, Inc; EP1815866; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.283

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

76.82

Lipinski Number

Veber Number

Reaxys ID 19332482 View in Reaxys

121/181

238/378

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CAS Registry Number: 1166813-24-6 Linear Structure Formula: C19H17F4N7 Molecular Formula: C19H17F4N7 Molecular Weight: 419.384 InChI Key: KLOXENUKOZCWFV-UHFFFAOYSA-N Note:

N F

F F F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332482View in Reaxys

Substance Name

283

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.78

Measurement pX

6.11

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human] Target Mutant/Chimera Details

androgen receptor [human]:Wild

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3 of 3

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332482View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.78

Measurement pX

6.11

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332482View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 11752122 View in Reaxys

122/181 Chemical Name: 6-(5-(4-(1H-indol-3-ylmethyl)-piperazin-1-yl)pyridin-3-yl)-isoquinoline Linear Structure Formula: C27H25N5 Molecular Formula: C27H25N5 Molecular Weight: 419.529 InChI Key: SCWIRSFEUFHHKA-UHFFFAOYSA-N Note:

N N

Patent-Specific Data (2)

240/378

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Location in Patent References Claim

Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); (A1) English, View in Reaxys Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.514

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

48.05

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (400 MHz, DMSO-D6) δ ppm 1.89 (s, 2H) 2.50 (m, 4H) 2.60 (m, 4H) 7.02 (m, 2H) 7.27 (d, J=2.46 Hz, 1H) 7.36 (d, J=7.98 Hz, 1H) 7.68 (m, 2H) 7.87 (d, J=5.83 Hz, 1H) 8.05 (dd, J=8.59, 1.53 Hz, 1H) 8.22 (d, J=8.90 Hz, 1H) 8.34 (m, 2H) 8.44 (d, J=1.84 Hz, 1H) 8.54 (d, J=5.83 Hz, 1H) 9.35 (s, 1H) 10.93 (s, 1H)

Signals [ppm]

1.89; 2.5; 2.6; 7.02; 7.27; 7.36; 7.68; 7.87; 8.05; 8.22; 8.34; 8.44; 8.54; 9.35; 10.93

Kind of signal

s, 2H; m, 4H; m, 4H; m, 2H; d, J=2.46 Hz, 1H; d, J=7.98 Hz, 1H; m, 2H; d, J=5.83 Hz, 1H; dd, J=8.59, 1.53 Hz, 1H; d, J=8.90 Hz, 1H; m, 2H; d, J=1.84 Hz, 1H; d, J=5.83 Hz, 1H; s, 1H; s, 1H

Molecular peak

References Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); (A1) English, View in Reaxys

Medchem (24) 1 of 24

Target Name

Mitogen-activated protein kinase 1

Target Synonyms

at1g10210; atmpk1; erk-2; erk2 (mitogen-activated protein kinase 1); ert1 (mitogen-activated protein kinase 1); extracellular signal-regulated kinase 2 (mitogen-activated protein kinase 1); f14n23.9; loc_os06g06090; m phase map kinase; map kinase 1; map kinase 2; map kinase 6 (mitogen-activated protein kinase 1); map kinase isoform p42; map kinase mkp1; mapk (mitogen-activated protein kinase 1); mapk 1; mapk 2; mapk1 (mitogen-activated protein kinase 1); mapk6 (mitogen-activated protein kinase 1); mbp kinase; mitogen-activated protein kinase 1; mitogen-activated protein kinase 2 (mitogen-activated protein kinase 1); mkp1 (mitogen-activated protein kinase 1); mpk1 (mitogen-activated pro-

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tein kinase 1); myelin basic protein kinase; myelin xp42 protein kinase; os06g0154500; osjnba0085l11.14; osmapk6 (mitogen-activated protein kinase 1); ossipk; p42-mapk; prkm1; prkm2; sipk Target, Subunit, Species Mitogen-activated protein kinase 1

2 of 24

Target Mutant/Chimera Details

Mitogen-activated protein kinase 1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against ERK2 was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-alpha serine/threonine-protein kinase

Target Synonyms

akt (rac-alpha serine/threonine-protein kinase); akt-1; akt-2; akt1 (rac-alpha serine/threonine-protein kinase); akt1 kinase; c12d8.10; f28h6.1; pkb; pkb akt-1; pkb akt-2; pkb alpha; protein kinase akt-1; protein kinase b (rac-alpha serine/threonine-protein kinase); protein kinase b akt-1; protein kinase b akt-2; protein kinase b alpha; protein kinase b, alpha; proto-oncogene c-akt; rac; rac-alpha serine/threonine-protein kinase; rac-pk-alpha; serine/ threonine-protein kinase akt-1; serine/threonine-protein kinase akt-2; thymoma viral protooncogene; xakt

Target, Subunit, Species RAC-alpha serine/threonine-protein kinase

3 of 24

Target Mutant/Chimera Details

RAC-alpha serine/threonine-protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of the compound against 1 nM His-Akt1-S36 using 5 uM Biotin-BADpeptide and 5 uM 33P-ATP upon incubation with 20 mM HEPES buffer, pH 7.5 for 30 min at RT; Value range = 0 - 100

Substance RN

11752122View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

100

Target Name

c-src tyrosine kinase

Target Synonyms

c-src tyrosine kinase

Target, Subunit, Species c-src tyrosine kinase Target Mutant/Chimera Details

c-src tyrosine kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against SRC was determined by using 33P-ATP

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4 of 24

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

cAMP-dependent protein kinase

Target Synonyms

3',5' camp-dependent protein kinase; 3',5'-camp-dependent protein kinase; adenosine 3', 5'-cyclophosphate-dependent protein kinase; atp:protein phosphotransferase (camp-dependent); camp-dependent protein kinase; camp-dependent protein kinase, intrinsic catalyst; cyclic amp-dependent protein kinase

Target, Subunit, Species cAMP-dependent protein kinase

5 of 24

Target Mutant/Chimera Details

cAMP-dependent protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against PKA was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-gamma serine/threonine-protein kinase

Target Synonyms

akt3 (rac-gamma serine/threonine-protein kinase); pkb gamma; pkbg; protein kinase akt-3; protein kinase b gamma; rac-gamma serine/threonine-protein kinase; rac-pk-gamma; stk-2

Target, Subunit, Species RAC-gamma serine/threonine-protein kinase

6 of 24

Target Mutant/Chimera Details

RAC-gamma serine/threonine-protein kinase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of the compound against AKT3 using 33P-ATP upon incubation for 30 min at RT; Value range = 0 - 100

Substance RN

11752122View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Percent inhibition

Qualitative value

Quantitative value

100

Target Name

Casein kinase II subunit alpha

Target Synonyms

5c2.270; ack2 (casein kinase ii subunit alpha); at2g23070; b0205.7; casein kinase ii subunit alpha; casein kinase ii subunit alpha, chloroplastic; cask (casein kinase ii subunit alpha); cask-ii-a; cg17520; ck ii; ck ii alpha; ck ii subunit alpha; ck-1b (casein kinase ii subunit alpha); ck2-alpha; ck2a1; cka (casein kinase ii subunit alpha); cka1 (casein kinase ii subunit alpha); ckiia; ckiialpha; csnk2a1; csnk2a1 protein; ddb_g0276885; f21p24.13; kin-3; ncu03124; orb5; spac23c11.11; ta10630; tackiialpha; tp04_0659; yil035c

Target, Subunit, Species Casein kinase II subunit alpha Target Mutant/Chimera Details

Casein kinase II subunit alpha:Wild

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7 of 24

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against CK2 was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

MAP kinase-activated protein kinase 2

Target Synonyms

map kinase-activated protein kinase 2; mapk-activated protein kinase 2; mapkap kinase 2; mapkap-k2; mapkapk-2; mapkapk2; mk-2; mk2; p45-54 hsp27 kinase; rps6kc1 (map kinase-activated protein kinase 2)

Target, Subunit, Species MAP kinase-activated protein kinase 2

8 of 24

Target Mutant/Chimera Details

MAP kinase-activated protein kinase 2:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against MAPKAP kinase 2 was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-beta serine/threonine-protein kinase

Target Synonyms

akt (rac-beta serine/threonine-protein kinase); akt1 (rac-beta serine/threonine-protein kinase); akt2 (rac-beta serine/threonine-protein kinase); cg4006; dakt; dakt1; drac-pk; pkb; pkb beta; protein kinase akt-2; protein kinase b (rac-beta serine/threonine-protein kinase); protein kinase b beta; rac serine/threonine-protein kinase; rac-beta serine/threonine-protein kinase; rac-pk-beta

Target, Subunit, Species RAC-beta serine/threonine-protein kinase

9 of 24

Target Mutant/Chimera Details

RAC-beta serine/threonine-protein kinase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of the compound against AKT2 using 33P-ATP upon incubation for 30 min at RT; Value range = 0 - 100

Substance RN

11752122View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Percent inhibition

Qualitative value

Quantitative value

100

Target Name

Serine/threonine-protein kinase Chk1

Target Synonyms

cbg06670; cell cycle checkpoint kinase; cg17161; checkpoint kinase 1; checkpoint kinase-1; chek1; chk-1; chk1 (serine/threonine-protein kinase chk1); chk1 checkpoint homolog; chk1 homolog; grp (serine/threonine-protein kinase chk1); protein grapes; rad27 (serine/threonine-protein kinase chk1); serine/threonine-protein kinase chk-1; serine/threo-

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nine-protein kinase chk1; serine/threonine-protein kinase grp; spcc1259.13; um11087; xchk1; y39h10a.7; ybr1742; ybr274w Target, Subunit, Species Serine/threonine-protein kinase Chk1

10 of 24

Target Mutant/Chimera Details

Serine/threonine-protein kinase Chk1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against CHK1 was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Cyclin-dependent kinase 1

Target Synonyms

an4182; cao19.11337; cao19.3856; cbg10007; cdc2 (cyclin-dependent kinase 1); cdc28 (cyclin-dependent kinase 1); cdc28a; cdc2a (cyclin-dependent kinase 1); cdcb; cdk-1; cdk1; cdkn1 (cyclin-dependent kinase 1); cell division control protein 2; cell division control protein 2 homolog (cyclin-dependent kinase 1); cell division control protein 28; cell division control protein 28 homolog; cell division protein kinase 1 (cyclin-dependent kinase 1); cell division protein kinase 2 (cyclin-dependent kinase 1); cg5363; cyclin-dependent kinase 1; ddb_g0272813; ecu08_1920; hsl5; ncc-1 (cyclin-dependent kinase 1); never in mitosis protein x; nimx; p34 protein kinase; p34cdc2 (cyclin-dependent kinase 1); pi002; spbc11b10.09; srm5; swo2; t05g5.3; ybr1211; ybr160w

Target, Subunit, Species Cyclin-dependent kinase 1

11 of 24

Target Mutant/Chimera Details

Cyclin-dependent kinase 1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against CDC2 was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

protein kinase C

Target Synonyms

atp:protein phosphotransferase (diacylglycerol-dependent); diacylglycerol-activated phospholipid-dependent pkc; diacylglycerol-activated phospholipid-dependent protein kinase c; pkc (protein kinase c); pkc1 (protein kinase c); protein kinase c

Target, Subunit, Species protein kinase C Target Mutant/Chimera Details

protein kinase C:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against PKC was determined by using 33P-ATP

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12 of 24

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Serine/threonine-protein kinase Sgk1

Target Synonyms

cbg16386; qtsa-19250; serine/threonine-protein kinase sgk-1; serine/threonine-protein kinase sgk1; serum- and glucocorticoid-inducible kinase homolog; serum/glucocorticoidregulated kinase 1; sgk; sgk-1; sgk1; w10g6.2; wu:fc20a09

Target, Subunit, Species Serine/threonine-protein kinase Sgk1

13 of 24

Target Mutant/Chimera Details

Serine/threonine-protein kinase Sgk1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against SGK was determined by using 33P-ATP

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Serine/threonine-protein kinase Sgk1

Target Synonyms

Target, Subunit, Species Serine/threonine-protein kinase Sgk1 Target Mutant/Chimera Details

Serine/threonine-protein kinase Sgk1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against SGK using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

MAP kinase-activated protein kinase 2

Target Synonyms

Target, Subunit, Species MAP kinase-activated protein kinase 2

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Target Mutant/Chimera Details

MAP kinase-activated protein kinase 2:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against MAPKAP2 using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Cyclin-dependent kinase 1

Target Synonyms

Target, Subunit, Species Cyclin-dependent kinase 1 Target Mutant/Chimera Details

Cyclin-dependent kinase 1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against Cdc2 using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Casein kinase II subunit alpha

Target Synonyms

Target, Subunit, Species Casein kinase II subunit alpha Target Mutant/Chimera Details

Casein kinase II subunit alpha:Wild

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Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against CK2 using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

cAMP-dependent protein kinase

Target Synonyms

Target, Subunit, Species cAMP-dependent protein kinase Target Mutant/Chimera Details

cAMP-dependent protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against PKA using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-gamma serine/threonine-protein kinase

Target Synonyms

akt3 (rac-gamma serine/threonine-protein kinase); pkb gamma; pkbg; protein kinase akt-3; protein kinase b gamma; rac-gamma serine/threonine-protein kinase; rac-pk-gamma; stk-2

Target, Subunit, Species RAC-gamma serine/threonine-protein kinase Target Mutant/Chimera Details

RAC-gamma serine/threonine-protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against Akt3 using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

248/378

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Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-beta serine/threonine-protein kinase

Target Synonyms

Target, Subunit, Species RAC-beta serine/threonine-protein kinase Target Mutant/Chimera Details

RAC-beta serine/threonine-protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against Akt2 using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

c-src tyrosine kinase

Target Synonyms

c-src tyrosine kinase

Target, Subunit, Species c-src tyrosine kinase Target Mutant/Chimera Details

c-src tyrosine kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against SRC kinase using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-alpha serine/threonine-protein kinase

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Target Synonyms

Target, Subunit, Species RAC-alpha serine/threonine-protein kinase Target Mutant/Chimera Details

RAC-alpha serine/threonine-protein kinase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of His-Akt1-S36 (1 nM) using biotin-BAD-peptide (5 uM) as substrate in presence of 33P-ATP upon incubation in HEPES (pH 7.5) for 30 min at RT at 1 uM concentration; Range = 0-100

Substance RN

11752122View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Percent inhibition

Qualitative value

Quantitative value

100

Target Name

protein kinase C

Target Synonyms

Target, Subunit, Species protein kinase C Target Mutant/Chimera Details

protein kinase C:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against PKC using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Mitogen-activated protein kinase 1

Target Synonyms

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gen-activated protein kinase 1; mitogen-activated protein kinase 2 (mitogen-activated protein kinase 1); mkp1 (mitogen-activated protein kinase 1); mpk1 (mitogen-activated protein kinase 1); myelin basic protein kinase; myelin xp42 protein kinase; os06g0154500; osjnba0085l11.14; osmapk6 (mitogen-activated protein kinase 1); ossipk; p42-mapk; prkm1; prkm2; sipk Target, Subunit, Species Mitogen-activated protein kinase 1 Target Mutant/Chimera Details

Mitogen-activated protein kinase 1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against Erk2 using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Serine/threonine-protein kinase Chk1

Target Synonyms

Target, Subunit, Species Serine/threonine-protein kinase Chk1 Target Mutant/Chimera Details

Serine/threonine-protein kinase Chk1:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against Chk1using biotinylated peptide substrate

Substance RN

11752122View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 20623282 View in Reaxys

123/181

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CAS Registry Number: 1240299-44-8 Chemical Name: 6-{4-[(5-fluoro-1H-indol-3-yl)methyl]piperazin-1-yl}-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine Linear Structure Formula: C19H19F4N7 Molecular Formula: C19H19F4N7 Molecular Weight: 421.4 InChI Key: WEJKWKWMCGZGBL-UHFFFAOYSA-N Note:

F N N HN

N F

F F

Substance Label (1) Label References 12

LogP

4.082

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

65.34

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Location

Page/Page column 103

Comment (NMR Spectroscopy)

Signals given

Page/Page column 103

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

20623282View in Reaxys

Substance Name

252/378

2017-11-11 00:22:14

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.4

Measurement pX

5.47

Concomitants: Compound RN

24140449; 1723797

Concomitants: Compound name

Penicillin-Streptomycin; Glutamine

Concomitants: Compound role

VPR; VPR

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Cells/Cell Lines

LNCaP clone FGC

Substance RN

20623282View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.4

Measurement pX

5.47

Patent; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; (181 pag.); WO2010/92371; (A1); (2010), View in Reaxys 3 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Cells/Cell Lines

LNCaP clone FGC

Substance RN

20623282View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.4

Measurement pX

5.47

Patent; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; (181 pag.); WO2010/92371; (A1); (2010), View in Reaxys

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Reaxys ID 632470 View in Reaxys

124/181 CAS Registry Number: 58434-19-8 Chemical Name: N-(4-indol-3-ylmethyl-piperazin-1-yl)-3,4,5-trimethoxy-benzamide Linear Structure Formula: C23H28N4O4 Molecular Formula: C23H28N4O4 Molecular Weight: 424.5 Type of Substance: heterocyclic InChI Key: MYYUMVOCRJWWIZ-UHFFFAOYSA-N Note:

NH O

O O

Substance Label (2) Label References 34

Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.146

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

79.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

206 - 208

Patent; Hoechst; FR2272673; (1975); DE2522143; Chem.Abstr.; vol. 84; nb. 90183, View in Reaxys; Glamkowski et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1485, View in Reaxys Medchem (2) 1 of 2

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Antihypertensive activity was tested using spontaneous hypertensive rat by a standard indirect tail cuff method on day 3 at oral dose of 100 mg/kg

Biological Species/NCBI Rattus norvegicus ID Substance RN

632470View in Reaxys

Substance Route of Adm.

oral administration

Measurement Parameter

Activity

Unit

Qualitative value

Quantitative value

-36

Glamkowski; Reitano; Woodward; Journal of Medicinal Chemistry; vol. 20; nb. 11; (1977); p. 1485 - 1489, View in Reaxys 2 of 2

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Antihypertensive activity was tested using spontaneous hypertensive rat by a standard indirect tail cuff method on day 1 at oral dose of 100 mg/kg

Biological Species/NCBI Rattus norvegicus ID Substance RN

632470View in Reaxys

Substance Route of Adm.

oral administration

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Measurement Parameter

Activity

Unit

Qualitative value

Quantitative value

-20

Glamkowski; Reitano; Woodward; Journal of Medicinal Chemistry; vol. 20; nb. 11; (1977); p. 1485 - 1489, View in Reaxys

Reaxys ID 25673014 View in Reaxys

125/181 CAS Registry Number: 1166818-94-5 Linear Structure Formula: C21H18F3N7 Molecular Formula: C21H18F3N7 Molecular Weight: 425.416 InChI Key: GIYGJFXAZCJZHE-UHFFFAOYSA-N Note:

N N

F F

Druglikeness (1) 1 of 1

LogP

5.223

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

76.25

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human] Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against levels of the androgen receptor in the human LNCaP prostate carcinoma cell line upon incubation for 20-22 hours at 37 degree C

Cells/Cell Lines

LN-CAP

Substance RN

25673014View in Reaxys

Qualitative Results

Not determined

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Measurement Parameter

Qualitative

Measurement Object

Levels of the androgen receptor

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 2

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of compound against rat androgen receptor ligand binding domain by using fluorescence polarization assay

Substance RN

25673014View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Reaxys ID 19332518 View in Reaxys

126/181

CAS Registry Number: 1166813-18-8 Linear Structure Formula: C20H17F3N8 Molecular Formula: C20H17F3N8 Molecular Weight: 426.404 InChI Key: DQEVPJDXAAJOMS-UHFFFAOYSA-N Note:

N N

F F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

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Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332518View in Reaxys

Substance Name

278

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.65

Measurement pX

6.19

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332518View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.65

Measurement pX

6.19

Target Name

androgen receptor [Rattus norvegicus]

257/378

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Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332518View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 20623289 View in Reaxys

127/181 CAS Registry Number: 1240299-45-9 Chemical Name: 3-({4-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl}methyl)-1H-indole-5carbonitrile Linear Structure Formula: C20H19F3N8 Molecular Formula: C20H19F3N8 Molecular Weight: 428.42 InChI Key: VOTLZURATNBCQE-UHFFFAOYSA-N Note:

N N

N H

Substance Label (1) Label References 13

LogP

3.644

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

89.13

Lipinski Number

Veber Number

NMR Spectroscopy (1)

258/378

2017-11-11 00:22:14

1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Location

Page/Page column 103

Comment (NMR Spectroscopy)

Signals given

Page/Page column 103

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

20623289View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound RN

24140449; 1723797

Concomitants: Compound name

Penicillin-Streptomycin; Glutamine

Concomitants: Compound role

VPR; VPR

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Cells/Cell Lines

LNCaP clone FGC

Substance RN

20623289View in Reaxys

Substance Name

Measurement Parameter

IC50

259/378

2017-11-11 00:22:14

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Patent; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; (181 pag.); WO2010/92371; (A1); (2010), View in Reaxys 3 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Cells/Cell Lines

LNCaP clone FGC

Substance RN

20623289View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Patent; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; (181 pag.); WO2010/92371; (A1); (2010), View in Reaxys

Reaxys ID 31639373 View in Reaxys

128/181 Chemical Name: 1-benzyl-N-(3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-yl)-1H-pyrazole-4-carboxamide Linear Structure Formula: C25H28N6O Molecular Formula: C25H28N6O Molecular Weight: 428.537 InChI Key: NOJHMLGDGWPYAT-UHFFFAOYSA-N Note:

N H N

N O

Substance Label (1) Label References compound 3

Druglikeness (1) 1 of 1

LogP

2.698

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

69.19

Lipinski Number

260/378

2017-11-11 00:22:14

Veber Number

Crystal Property Description (1) Colour & Other Location Properties yellow

References

Paragraph 0667

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

Location

Paragraph 0667

Signals [ppm]

2.21; 2.25 - 2.4; 3.55; 5.39; 7.19; 7.27 - 7.39; 7.83; 8.06; 8.41; 9.69; 10.85

Kind of signal

s, 3H; m, 8H; s, 2H; s, 2H; d, 1H, J=1.2 Hz; m, 7H; s, 1H; s, 1H; s, 1H; s, 1H; s, 1H

NMR (DMSO-d6) δ 2.21 (s, 3H), 2.25-2.40 (m, 8H), 3.55 (s, 2H), 5.39 (s, 2H), 7.19 (d, 1H, J=1.2 Hz), 7.27-7.39 (m, 7H), 7.83 (s, 1H), 8.06 (s, 1H), 8.41 (s, 1H), 9.69 (s, 1H), 10.85 (s, 1H)

Patent; Phoenix Molecular Designs; DUNN, Sandra E.; JAYANTHAN, Aarthi; NAGIREDDY, Jaipal Reddy; ANNEDI, Subhash; VAN DRIE, John H.; DAYNARD, Timothy S.; HUYNH, My-my; (81 pag.); US2017/240549; (2017); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

Paragraph 0667

Peak

References

429 m/z

Reaxys ID 19332475 View in Reaxys

129/181

CAS Registry Number: 1166813-20-2 Linear Structure Formula: C19H17ClF3N7 Molecular Formula: C19H17ClF3N7 Molecular Weight: 435.839 InChI Key: MZDUDKZZKOVNNE-UHFFFAOYSA-N Note:

N N

N Cl F F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

261/378

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Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

Substance RN

19332475View in Reaxys

Substance Name

280

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.78

Measurement pX

6.11

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332475View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.78

Measurement pX

6.11

Target Name

androgen receptor [Rattus norvegicus]

262/378

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Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332475View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 13059875 View in Reaxys N

130/181 Linear Structure Formula: C25H26N8 Molecular Formula: C25H26N8 Molecular Weight: 438.535 InChI Key: OSDSSWSLYXXJIH-UHFFFAOYSA-N Note:

N N

N HN

NH 2

Patent-Specific Data (1) References Patent; SCHERING CORPORATION; WO2007/126964; (2007); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.283

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.75

Lipinski Number

Veber Number

Medchem (4) 1 of 4

Target Name

RAC-alpha serine/threonine-protein kinase [human]

Target Synonyms

akt1; pkb; pkb alpha; protein kinase b; protein kinase b alpha; proto-oncogene c-akt; rac; rac-alpha serine/threonine-protein kinase; rac-pk-alpha

Target Uniprot ID

p31749

263/378

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Target PDB ID

1h10; 1unp; 1unq; 1unr; 2uvm; 2uzr; 2uzs; 3cqu; 3cqw; 3mv5; 3mvh; 3o96; 3ocb; 3ow4; 3qkk; 3qkl; 3qkm; 4ejn; 4ekk; 4ekl; 4gv1

Target, Subunit, Species RAC-alpha serine/threonine-protein kinase [human]

2 of 4

Target Mutant/Chimera Details

RAC-alpha serine/threonine-protein kinase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against human AKT1 expressed in Sf9 cells using [gamma-33P]-ATP (0.25 uCi) and biotinylated peptide (1 uM) upon incubation for 2 h at RT in 50 mM Tris-HCl buffer, pH 7.5; Range = 0.00098 to 8.1 uM

Cells/Cell Lines

Sf9

Substance RN

13059875View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

8.1

Measurement pX

5.09

Target Name

RAC-beta serine/threonine-protein kinase

Target Synonyms

Target, Subunit, Species RAC-beta serine/threonine-protein kinase

3 of 4

Target Mutant/Chimera Details

RAC-beta serine/threonine-protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against AKT2

Substance RN

13059875View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-gamma serine/threonine-protein kinase

Target Synonyms

akt3 (rac-gamma serine/threonine-protein kinase); pkb gamma; pkbg; protein kinase akt-3; protein kinase b gamma; rac-gamma serine/threonine-protein kinase; rac-pk-gamma; stk-2

Target, Subunit, Species RAC-gamma serine/threonine-protein kinase Target Mutant/Chimera Details

RAC-gamma serine/threonine-protein kinase:Wild

Substance Action on Target

Inhibitor

264/378

2017-11-11 00:22:14

4 of 4

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against AKT3

Substance RN

13059875View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

RAC-alpha serine/threonine-protein kinase [human]

Target Synonyms

akt1; pkb; pkb alpha; protein kinase b; protein kinase b alpha; proto-oncogene c-akt; rac; rac-alpha serine/threonine-protein kinase; rac-pk-alpha

Target Uniprot ID

p31749

Target PDB ID

1h10; 1unp; 1unq; 1unr; 2uvm; 2uzr; 2uzs; 3cqu; 3cqw; 3mv5; 3mvh; 3o96; 3ocb; 3ow4; 3qkk; 3qkl; 3qkm; 4ejn; 4ekk; 4ekl; 4gv1

Target, Subunit, Species RAC-alpha serine/threonine-protein kinase [human] Target Mutant/Chimera Details

RAC-alpha serine/threonine-protein kinase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against human Akt1 expressed in Sf9 cells using Bio-ahx-RPRAASF (1 uM) as substrate using [gamma-33P]ATP (0.25 uCi) upon incubation in 50 mM Tris-HCl, pH 7.5 at RT for 2 h; Range = 0.00098 - 8.1 uM

Cells/Cell Lines

Sf9

Substance RN

13059875View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

8.1

Measurement pX

5.09

Patent; SCHERING CORPORATION; WO2007/126964; (2007); (A2) English, View in Reaxys

Reaxys ID 9299383 View in Reaxys

131/181 Chemical Name: 8-chloro-11-{4-[(1H-indol-3-yl)methyl]piperazino}-5H-dibenzo[b,e][1,4]diazepine Linear Structure Formula: C26H24ClN5 Molecular Formula: C26H24ClN5 Molecular Weight: 441.963 Type of Substance: heterocyclic InChI Key: XRRJUQKQCOYQDM-UHFFFAOYSA-N Note:

H N Cl N N N HN

Substance Label (1)

265/378

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Label

References

18b

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.682

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.66

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

135

Solvent (Melting Point)

methanol; H2O

Comment (Melting Point)

Crystallization with 1 Mol(s) methanol

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

266/378

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Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 220; 263; 291 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

61659; 20417; 15848

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Medchem (3) 1 of 3

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]spiperone (0.3 nM) binding to rat striatal membranes Dopamine receptor D2 at 1 uM after 15 min incubation at 37 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID

2 of 3

Substance RN

9299383View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

dopamine receptor d4.4 [human]

Target Synonyms

dopamine receptor d4.4

Target, Subunit, Species dopamine receptor d4.4 [human] Target Mutant/Chimera Details

dopamine receptor d4.4 [human]:Wild

267/378

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Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]spiperone (0.3 nM) binding to cloned human Dopamine receptor 4.4 expressed in CHO-K1 cells at the concentration of 1 uM

Biological Species/NCBI Human ID

3 of 3

Cells/Cell Lines

CHO-K1

Substance RN

9299383View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]ketanserin (0.5 nM) binding to rat cortical menbranes 5hydroxytryptamine 2A receptor at 1 uM after 15 min incubation at 37 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID Substance RN

9299383View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Ketanserin

Concomitants: Compound role

RAD

Reaxys ID 22690399 View in Reaxys

132/181

268/378

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CAS Registry Number: 1381992-14-8 Chemical Name: 6-({2-[4-(1H-indol-3-ylmethyl)piperazin-1yl]ethyl}propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol Linear Structure Formula: C28H38N4O Molecular Formula: C28H38N4O Molecular Weight: 446.636 InChI Key: UHRDDHPBSKWWGI-UHFFFAOYSA-N Note:

OH N N

Druglikeness (1) 1 of 1

LogP

3.861

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

45.74

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys Medchem (3) 1 of 3

Target Name

Dopamine 2 long receptor [Rattus norvegicus]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [Rattus norvegicus] Target Mutant/Chimera Details

Dopamine 2 long receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition constant of compound towards rat dopamine receptor D2L expressed in HEK 293 cells using [3H]Spiroperidol upon incubation at 30 degree C for 1 h in 50 mM TRISHCl, pH 7.4

Biological Species/NCBI Rattus norvegicus ID Cells/Cell Lines

HEK 293

269/378

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Substance RN

22690399View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

82.1

Deviation

7.1

Measurement pX

7.09

Concomitants: Compound name

[3H]SPIROPERIDOL

Concomitants: Compound role

RAD

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys 2 of 3

Target Name

D(3) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p19020

Target, Subunit, Species D(3) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(3) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition constant of compound towards rat dopamine receptor D3 expressed in HEK 293 cells using [3H]Spiroperidol upon incubation at 30 degree C for 1 h in 50 mM TRIS-HCl, pH 7.4

Biological Species/NCBI Rattus norvegicus ID Cells/Cell Lines

HEK 293

Substance RN

22690399View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

3.2

Deviation

0.32

Measurement pX

8.49

Concomitants: Compound name

[3H]SPIROPERIDOL

Concomitants: Compound role

RAD

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys 3 of 3

Target Name

Dopamine 2 long receptor [Rattus norvegicus]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [Rattus norvegicus] Target Mutant/Chimera Details

Dopamine 2 long receptor [Rattus norvegicus]:Wild

270/378

2017-11-11 00:22:14

Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity is the ratio of inhibition constant of compound towards rat dopamine receptor D2L to that of dopamine receptor D3 expressed in HEK 293 cells

Biological Species/NCBI Rattus norvegicus ID Cells/Cell Lines

HEK 293

Substance RN

22690399View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys

Reaxys ID 9302328 View in Reaxys

133/181 Chemical Name: 8-chloro-11-{4-[(5-hydroxy-1H-indol-3yl)methyl]piperazino}-5H-dibenzo[b,e][1,4]diazepine Linear Structure Formula: C26H24ClN5O Molecular Formula: C26H24ClN5O Molecular Weight: 457.962 Type of Substance: heterocyclic InChI Key: IMTHIGQRYFSTIP-UHFFFAOYSA-N Note:

H N Cl N N N HN

Substance Label (1) Label References 20

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.276

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

66.89

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow - brown

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- tetradeuteriomethanol scopy)

271/378

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Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 226; 264; 298 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

37153; 17378; 12882

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Medchem (3) 1 of 3

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

272/378

2017-11-11 00:22:14

Bioassay Details

In vitro percent inhibition of [3H]spiperone (0.3 nM) binding to rat striatal membranes Dopamine receptor D2 at 1 uM after 15 min incubation at 37 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID

2 of 3

Substance RN

9302328View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

dopamine receptor d4.4 [human]

Target Synonyms

dopamine receptor d4.4

Target, Subunit, Species dopamine receptor d4.4 [human] Target Mutant/Chimera Details

dopamine receptor d4.4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]spiperone (0.3 nM) binding to cloned human Dopamine receptor 4.4 expressed in CHO-K1 cells at the concentration of 1 uM

Biological Species/NCBI Human ID

3 of 3

Cells/Cell Lines

CHO-K1

Substance RN

9302328View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

273/378

2017-11-11 00:22:14

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]ketanserin (0.5 nM) binding to rat cortical menbranes 5hydroxytryptamine 2A receptor at 1 uM after 15 min incubation at 37 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID Substance RN

9302328View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Ketanserin

Concomitants: Compound role

RAD

Reaxys ID 19332393 View in Reaxys

134/181

CAS Registry Number: 1166813-31-5 Linear Structure Formula: C19H18BrF2N7 Molecular Formula: C19H18BrF2N7 Molecular Weight: 462.3 InChI Key: DZRBIROXFUGWJH-UHFFFAOYSA-N Note:

N N

N Br F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

274/378

2017-11-11 00:22:14

Substance RN

19332393View in Reaxys

Substance Name

288

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.3

Measurement pX

5.48

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332393View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

3.3

Measurement pX

5.48

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

275/378

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Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332393View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 6165617 View in Reaxys

135/181 Chemical Name: 2-<2-<4-((5-fluoro-1H-indol-3-yl)methyl)-1-piperazinyl>ethyl>-2H-naphth<1,8-cd>isothiazole 1,1-dioxide Linear Structure Formula: C25H25FN4O2S Molecular Formula: C25H25FN4O2S Molecular Weight: 464.564 Type of Substance: heterocyclic InChI Key: VDYVPBAJQCJILV-UHFFFAOYSA-N Note:

N N O O

Substance Label (1) Label References 20

Malleron, Jean-Luc; Gueremy, Claude; Mignani, Serge; Peyronel, Jean-Francois; Truchon, Alain; et al.; Journal of Medicinal Chemistry; vol. 36; nb. 9; (1993); p. 1194 - 1202, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.117

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.03

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

Solvent (Melting Point)

acetonitrile

Malleron, Jean-Luc; Gueremy, Claude; Mignani, Serge; Peyronel, Jean-Francois; Truchon, Alain; et al.; Journal of Medicinal Chemistry; vol. 36; nb. 9; (1993); p. 1194 - 1202, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Malleron, Jean-Luc; Gueremy, Claude; Mignani, Serge; Peyronel, Jean-Francois; Truchon, Alain; et al.; Journal of Medicinal Chemistry; vol. 36; nb. 9; (1993); p. 1194 - 1202, View in Reaxys Medchem (4)

276/378

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1 of 4

Target Name

Sodium-dependent serotonin transporter [Rattus norvegicus]

Target Synonyms

5ht transporter; 5htt; slc6a4; sodium-dependent serotonin transporter; solute carrier family 6 member 4

Target Uniprot ID

p31652

Target, Subunit, Species Sodium-dependent serotonin transporter [Rattus norvegicus] Target Mutant/Chimera Details

Sodium-dependent serotonin transporter [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID

2 of 4

Organs/Tissues

brain cortex

Cells/Cell Lines

cells

Cell Fraction

Membrane

Substance RN

6165617View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

Quantitative value

Measurement pX

8.3

Concomitants: Compound RN

7467879; 612584

Concomitants: Compound name

[3H]-Paroxetine; Indalpine

Concomitants: Compound role

RAD; NSB

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

brain cortex

Cells/Cell Lines

cells

Cell Fraction

Membrane

277/378

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3 of 4

Substance RN

6165617View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Target Name

Alpha 1 adrenergic receptor [Rattus norvegicus]

Target Synonyms

alpha 1 adrenergic receptor

Target, Subunit, Species Alpha 1 adrenergic receptor [Rattus norvegicus] Target Mutant/Chimera Details

Alpha 1 adrenergic receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID

4 of 4

Organs/Tissues

brain cortex

Cells/Cell Lines

cells

Cell Fraction

Membrane

Substance RN

6165617View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

272944; 8728926

Concomitants: Compound name

Phentolamine; [3H]-Prazosin

Concomitants: Compound role

NSB; RAD

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus]

278/378

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Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

corpus striatum

Cells/Cell Lines

cells

Cell Fraction

Membrane

Substance RN

6165617View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

494008; 768345; 632204; 2820786

Concomitants: Compound name

Sulpiride; Prazosin; [3H]-Spiperone; Cinanserin

Concomitants: Compound role

NSB; COM; RAD; COM

Reaxys ID 21907482 View in Reaxys

136/181 CAS Registry Number: 1266605-65-5 Linear Structure Formula: C25H28F2N6O Molecular Formula: C25H28F2N6O Molecular Weight: 466.534 InChI Key: QLDMLILLPALAOJ-IQGLISFBSA-N Note:

N N N

F HN F

Druglikeness (1) 1 of 1

LogP

2.627

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

73.21

Lipinski Number

Veber Number

Medchem (14) 1 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

279/378

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Bioassay Details

In vitro minimum inhibitory concentration of compound against CANDIDA NEOFORMANS ATCC 36556 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

128

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 2 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against ASPERGILLUS FUMIGATUS ATCC 16424 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

Measurement pX

4.47

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 3 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against CANDIDA ALBICANS ATCC MYA-1003 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

128

Measurement pX

4.16

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 4 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

280/378

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Bioassay Details

In vitro minimum inhibitory concentration of compound against CANDIDA ALBICANS ATCC 90028 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

6.87

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 5 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against CANDIDA KRUSEI ATCC 6258 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

Measurement pX

5.07

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 6 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against CANDIDA ALBICANS ATCC 64548 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.5

Measurement pX

6.57

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 7 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

281/378

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Bioassay Details

In vitro minimum inhibitory concentration of compound against CANDIDA ALBICANS ATCC 36082 was determined using ALAMAR BLUE ASSAY

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.5

Measurement pX

6.57

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 307 - 310, View in Reaxys 8 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

274

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 9 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.54

Measurement pX

3.87

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 10 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

282/378

2017-11-11 00:22:14

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

1.07

Measurement pX

3.57

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 11 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

34.3

Measurement pX

2.07

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 12 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

274

Measurement pX

1.16

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 13 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

283/378

2017-11-11 00:22:14

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

1.07

Measurement pX

3.57

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 14 of 14

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

21907482View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

137

Measurement pX

1.47

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 31105801 View in Reaxys

137/181 Chemical Name: N-(2-(4-((1H-indol-3-yl)methyl)piperazin-1yl)-5-(trifluoromethyl)phenyl)furan-2-carboxamide Linear Structure Formula: C25H23F3N4O2 Molecular Formula: C25H23F3N4O2 Molecular Weight: 468.478 InChI Key: FFLVVHKDKKCYLU-UHFFFAOYSA-N Note:

F F

F O

N H

N NH

Substance Label (1) Label References 75

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Patent-Specific Data (1) References

284/378

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Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.408

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

64.51

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

Page/Page column 55

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

Page/Page column 55

References Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Medchem (1) 1 of 1

Target Name

Probable serine/threonine-protein kinase sky1

Target Synonyms

ddb_g0275627; probable serine/threonine-protein kinase sky1; sky1 (probable serine/ threonine-protein kinase sky1); srpk1-like kinase

Target, Subunit, Species Probable serine/threonine-protein kinase sky1 Target Mutant/Chimera Details

Probable serine/threonine-protein kinase sky1:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

31105801View in Reaxys

Substance Name

N-(2-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-5-(trifluoromethyl)phenyl)furan-2-carboxamide

Measurement Parameter

IC50

Unit

Quantitative value

74.9

Measurement pX

7.13

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

285/378

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Reaxys ID 12817239 View in Reaxys

138/181 Linear Structure Formula: C27H33N7O Molecular Formula: C27H33N7O Molecular Weight: 471.605 InChI Key: XTXCESRFEUTRRC-VWLOTQADSA-N Note:

NH 2

HN N

N N

Patent-Specific Data (1) References Patent; SCHERING CORPORATION; WO2007/11623; (2007); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.594

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

103.17

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry)

Molecular peak

References Patent; SCHERING CORPORATION; WO2007/11623; (2007); (A1) English, View in Reaxys

Reaxys ID 9301970 View in Reaxys

139/181 CAS Registry Number: 507263-43-6 Chemical Name: 8-chloro-11-{4-[(5-methoxy-1H-indol-3yl)methyl]piperazino}-5H-dibenzo[b,e][1,4]diazepine Linear Structure Formula: C27H26ClN5O Molecular Formula: C27H26ClN5O Molecular Weight: 471.989 Type of Substance: heterocyclic InChI Key: ZRIRCTNRDXEQKJ-UHFFFAOYSA-N Note:

H N Cl N N N HN

Substance Label (1) Label References 18a

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.597

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.89

Lipinski Number

Veber Number

286/378

2017-11-11 00:22:14

Melting Point (1) 1 of 1

Melting Point [°C]

150 - 156

Solvent (Melting Point)

methanol; H2O

Comment (Melting Point)

Crystallization with 1 Mol(s) methanol

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CD2Cl2 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

ethanol

287/378

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Absorption Maxima (UV/ 223; 264; 298 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

25118; 20892; 16218

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys Medchem (3) 1 of 3

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]spiperone (0.3 nM) binding to rat striatal membranes Dopamine receptor D2 at 1 uM after 15 min incubation at 37 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID

2 of 3

Substance RN

9301970View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

dopamine receptor d4.4 [human]

Target Synonyms

dopamine receptor d4.4

Target, Subunit, Species dopamine receptor d4.4 [human] Target Mutant/Chimera Details

dopamine receptor d4.4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]spiperone (0.3 nM) binding to cloned human Dopamine receptor 4.4 expressed in CHO-K1 cells at the concentration of 1 uM

Biological Species/NCBI Human ID Cells/Cell Lines

CHO-K1

Substance RN

9301970View in Reaxys

Measurement Parameter

% Inhibition

288/378

2017-11-11 00:22:14

3 of 3

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Spiperone

Concomitants: Compound role

RAD

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of [3H]ketanserin (0.5 nM) binding to rat cortical menbranes 5hydroxytryptamine 2A receptor at 1 uM after 15 min incubation at 37 degree C in pH 7.4

Biological Species/NCBI Rattus norvegicus ID Substance RN

9301970View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Deviation

Concomitants: Compound name

[3H]Ketanserin

Concomitants: Compound role

RAD

Reaxys ID 12051632 View in Reaxys

140/181 Linear Structure Formula: C29H27N5O2 Molecular Formula: C29H27N5O2 Molecular Weight: 477.566 InChI Key: BMOKEYVONUEXPM-UHFFFAOYSA-N Note:

O NH N

O N N

Substance Label (1) Label References 262

Patent; KUDOS PHARMACEUTICALS LIMITED; MAYBRIDGE LIMITED; WO2004/80976; (2004); (A1) English, View in Reaxys

289/378

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Patent-Specific Data (1) References Patent; KUDOS PHARMACEUTICALS LIMITED; MAYBRIDGE LIMITED; WO2004/80976; (2004); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.69

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

80.8

Lipinski Number

Veber Number

Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; KUDOS PHARMACEUTICALS LIMITED; MAYBRIDGE LIMITED; WO2004/80976; (2004); (A1) English, View in Reaxys

Medchem (4) 1 of 4

Target Name

Poly [ADP-ribose] polymerase [human]

Target Synonyms

poly

Target, Subunit, Species Poly [ADP-ribose] polymerase [human] Target Mutant/Chimera Details

Poly [ADP-ribose] polymerase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound (dissolved in DMSO) against Poly (ADP-Ribose) Polymerase from HELA cells upon incubation in 25 mM HEPES, pH 7.4 for 10 min at 30 degree C

Biological Species/NCBI Human ID Cells/Cell Lines

HeLa

Substance RN

12051632View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.1

Measurement pX

Patent; Kudos Pharmaceuticals Limited; Maybridge Limited; US2005/59663; (2005); (A1) English, View in Reaxys 2 of 4

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Potentiation factor is the ratio of inhibitory concentration (IC50) of the compound (200 nM) to that of control against human HeLa cells growth upon incubation for 6 h at 37 degree C using SRB assay

Biological Species/NCBI Human ID Cells/Cell Lines

HeLa

290/378

2017-11-11 00:22:14

Substance RN

12051632View in Reaxys

Measurement Parameter

PF50

Qualitative value

Quantitative value

Patent; Kudos Pharmaceuticals Limited; Maybridge Limited; US2005/59663; (2005); (A1) English, View in Reaxys 3 of 4

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Potentiation Factor is the ratio between inhibitory concentration of the control human HeLa cells growth to that of growth in presence of 200 nM compound for 72 h was determined by sulforhodamine B (SRB) assay

Cells/Cell Lines

HeLa

Substance RN

12051632View in Reaxys

Measurement Parameter

PF50

Measurement Object

Cell growth

Qualitative value

>=C

Quantitative value

Patent; KUDOS PHARMACEUTICALS LIMITED; MAYBRIDGE LIMITED; WO2004/80976; (2004); (A1) English, View in Reaxys 4 of 4

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HeLa

Substance RN

12051632View in Reaxys

Measurement Parameter

PF50

Measurement Object

Cell growth

Qualitative value

>=C

Quantitative value

Patent; Vincent Junior M Loh; Niall Morrison Barr Martin; Graeme Cameron Smith; Stephen Philip Jackson; Xiao-Ling Fan Cockcroft; Ian Timothy Williams Matthews; Keith Allan Menear; Frank Kerrigan; Alan Ashworth; US7449464; (B2); (2008), View in Reaxys

Reaxys ID 31105712 View in Reaxys

141/181

291/378

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Chemical Name: N-(2-(4-((1H-indol-3-yl)methyl)piperazin-1yl)-5-(trifluoromethyl)phenyl)picolinamide Linear Structure Formula: C26H24F3N5O Molecular Formula: C26H24F3N5O Molecular Weight: 479.505 InChI Key: HGUWBZCQIAPPLU-UHFFFAOYSA-N Note:

F F

F O

N H

N NH

Substance Label (1) Label References 38

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.545

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

64.26

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1Η NMR (400 MHz, DMSO) δ 11.031 (s, IH), 10.945 (s, IH), 8.771-8.768 (d, J = 1.4 Hz, IH), 8.270-8.260 (d, J = 4.4 Hz, IH), 8.177-8.158 (d, J = 7.7 Hz, IH), 8.115-8.092 (td, J = 7.7, 1.6 Hz, IH), 7.715-7.695 (d, J = 7.9 Hz, IH), 7.671-7.640 (ddd, J = 7.5, 4.8, 1.2 Hz, IH), 7.453 - 7.403 (m, 3H), 7.320-7.316 (d, J = 1.8 Hz, IH), 7.144-7.108 (t, J = 7.2 Hz, IH), 7.035-7.017 (t, J = 7.1 Hz, IH), 3.847 (s, 2H), 2.942 (s, 4H), 2.732 (s, 4H).

Location

Page/Page column 47

References Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Medchem (1) 1 of 1

Target Name

Probable serine/threonine-protein kinase sky1

Target Synonyms

ddb_g0275627; probable serine/threonine-protein kinase sky1; sky1 (probable serine/ threonine-protein kinase sky1); srpk1-like kinase

292/378

2017-11-11 00:22:14

Target, Subunit, Species Probable serine/threonine-protein kinase sky1 Target Mutant/Chimera Details

Probable serine/threonine-protein kinase sky1:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

31105712View in Reaxys

Substance Name

N-(2-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-5-(trifluoromethyl)phenyl)picolinamide

Measurement Parameter

IC50

Unit

Quantitative value

31.3

Measurement pX

7.5

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Reaxys ID 19332483 View in Reaxys

142/181

CAS Registry Number: 1166813-22-4 Linear Structure Formula: C19H17BrF3N7 Molecular Formula: C19H17BrF3N7 Molecular Weight: 480.29 InChI Key: JSNIQHXGQRJBCK-UHFFFAOYSA-N Note:

N N

N Br F F

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

399.9

Comment (NMR Spectroscopy)

Signals given

Molecular peak

References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

protein expression

Cells/Cell Lines

LN-CAP

293/378

2017-11-11 00:22:14

Substance RN

19332483View in Reaxys

Substance Name

281

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.8

Measurement pX

6.1

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81197; (2009); (A1) English, View in Reaxys 2 of 3

Target Name

androgen receptor [human]

Target Synonyms

androgen receptor; ar (androgen receptor); dhtr; dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p10275

Target PDB ID

Target, Subunit, Species androgen receptor [human]

3 of 3

Target Mutant/Chimera Details

androgen receptor [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

LN-CAP

Substance RN

19332483View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.8

Measurement pX

6.1

Target Name

androgen receptor [Rattus norvegicus]

Target Synonyms

androgen receptor; ar (androgen receptor); dihydrotestosterone receptor; nr3c4; nuclear receptor subfamily 3 group c member 4

Target Uniprot ID

p15207

Target PDB ID

1i37; 1i38; 1r4i; 1xnn; 2ihq; 2nw4; 3g0w

Target, Subunit, Species androgen receptor [Rattus norvegicus] Target Mutant/Chimera Details

androgen receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

294/378

2017-11-11 00:22:14

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound (dissolved in DMSO) against rat Androgen receptor by fluorescence polarisation (FP)-based competitive binding assay

Substance RN

19332483View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 22432078 View in Reaxys

143/181 CAS Registry Number: 1266605-77-9 Linear Structure Formula: C26H30F2N6O Molecular Formula: C26H30F2N6O Molecular Weight: 480.561 InChI Key: ZEAHDUPFIJMATC-NIYFSFCBSA-N Note:

N N

OH N

Druglikeness (1) 1 of 1

LogP

3.064

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

73.21

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

266

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

295/378

2017-11-11 00:22:14

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.26

Measurement pX

4.19

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.26

Measurement pX

4.19

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

4.16

Measurement pX

2.98

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

296/378

2017-11-11 00:22:14

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

66.59

Measurement pX

1.78

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.52

Measurement pX

3.89

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432078View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

66.59

Measurement pX

1.78

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 25844291 View in Reaxys

144/181

297/378

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CAS Registry Number: 1349521-83-0 Linear Structure Formula: C26H33FN6O2 Molecular Formula: C26H33FN6O2 Molecular Weight: 480.585 InChI Key: BZGZNRCUJNTVKR-UHFFFAOYSA-N Note:

HN F N N

NH N

O O

Druglikeness (1) 1 of 1

LogP

2.567

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

67.08

Lipinski Number

Veber Number

Medchem (4) 1 of 4

Target Name

5-Hydroxytryptamine 1A receptor

Target Synonyms

Target, Subunit, Species 5-Hydroxytryptamine 1A receptor

2 of 4

Target Mutant/Chimera Details

5-Hydroxytryptamine 1A receptor:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against 5-Hydroxytryptamine 1A receptor was determined

Substance RN

25844291View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

300

Measurement pX

6.52

Target Name

5-Hydroxytryptamine 1D receptor

Target Synonyms

5-ht-1d; 5-ht-1d-alpha; 5-ht1d; 5-hydroxytryptamine 1d receptor; 5-hydroxytryptamine receptor 1d; 5ht1d; cg7485; f1d; gpcr14; htr1d; htr1da; htrl (5-hydroxytryptamine 1d receptor); ocr (5-hydroxytryptamine 1d receptor); oct-tyrr; octyr99ab; rdc4; serotonin 1d alpha receptor; serotonin receptor 1d; tyr (5-hydroxytryptamine 1d receptor); tyr/oct-dro; tyramine/octopamine receptor; tyrr (5-hydroxytryptamine 1d receptor)

Target, Subunit, Species 5-Hydroxytryptamine 1D receptor Target Mutant/Chimera Details

5-Hydroxytryptamine 1D receptor:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against 5-hydroxytryptamine 1D receptor

298/378

2017-11-11 00:22:14

3 of 4

Substance RN

25844291View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

300

Measurement pX

6.52

Target Name

Sodium-dependent serotonin transporter [human]

Target Synonyms

5ht transporter; 5htt; htt (sodium-dependent serotonin transporter); sert; slc6a4; sodiumdependent serotonin transporter; solute carrier family 6 member 4

Target Uniprot ID

p31645

Target, Subunit, Species Sodium-dependent serotonin transporter [human] Target Mutant/Chimera Details

Sodium-dependent serotonin transporter [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against human Serotonin transporter was determined

Biological Species/NCBI Human ID

4 of 4

Substance RN

25844291View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

Quantitative value

Measurement pX

7.19

Target Name

5-Hydroxytryptamine 1B receptor

Target Synonyms

5-ht-1b; 5-ht-1d-beta; 5-ht1b; 5-ht1d subtype beta; 5-htr1b; 5-hydroxytryptamine 1b receptor; 5-hydroxytryptamine receptor 1b (5-hydroxytryptamine 1b receptor); 5ht1b; f01e11.5; htr1b; htr1db; s12 (5-hydroxytryptamine 1b receptor); serotonin 1d beta receptor; serotonin receptor 1b (5-hydroxytryptamine 1b receptor); tyra-2; tyramine receptor tyra-2

Target, Subunit, Species 5-Hydroxytryptamine 1B receptor Target Mutant/Chimera Details

5-Hydroxytryptamine 1B receptor:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against 5-Hydroxytryptamine 1B receptor was determined

Substance RN

25844291View in Reaxys

Measurement Parameter

IC50

Unit

Qualitative value

299/378

2017-11-11 00:22:14

Quantitative value

Measurement pX

7.3

Reaxys ID 22432084 View in Reaxys

145/181

N N

OH N

CAS Registry Number: 1266605-73-5 Chemical Name: (2R,3R)-2-(2,4-difluorophenyl)-3-[4-(5-fluoro-1H-indol-3-ylmethyl)-piperazin-1-yl]-1-(1H-1,2,4-triazol-1yl)butan-2-ol Linear Structure Formula: C25H27F3N6O Molecular Formula: C25H27F3N6O Molecular Weight: 484.524 InChI Key: VDCDFMWDUGKVSJ-CRICUBBOSA-N Note:

Druglikeness (1) 1 of 1

LogP

2.788

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

73.21

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) FAB (Fast atom bombardment); Spectrum

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID

300/378

2017-11-11 00:22:14

Substance RN

22432084View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

264

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432084View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.26

Measurement pX

4.19

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432084View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.52

Measurement pX

3.89

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432084View in Reaxys

301/378

2017-11-11 00:22:14

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

16.51

Measurement pX

2.38

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432084View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

66.04

Measurement pX

1.78

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432084View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.52

Measurement pX

3.89

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432084View in Reaxys

302/378

2017-11-11 00:22:14

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

33.02

Measurement pX

2.08

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 14181097 View in Reaxys

146/181 CAS Registry Number: 528859-48-5 Chemical Name: [851] N-[3-(4-methylpiperazin-1-yl)methyl-1Hindol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide; [19] N-[3-(4-methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5chloro-3-methylbenzo[b]thiophene-2-sulphonamide; N-[3-(4methylpiperazin-1-yl)methyl-1H-indol-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulphonamide Linear Structure Formula: C23H25ClN4O2S2 Molecular Formula: C23H25ClN4O2S2 Molecular Weight: 489.062 InChI Key: HYKSBOYHYALPPR-UHFFFAOYSA-N Note:

N N

O O

S NH

Substance Label (1) Label References 19

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys

Patent-Specific Data (3) Prophetic ComLocation in Patent References pound prophetic product

Claim

prophetic product

Patent; Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi; US2003/191124; (2003); (A1) English, View in Reaxys; Patent; Laboratorios del Dr. Esteve S.A.; EP2018861; (2009); (A1) English, View in Reaxys; Patent; Laboratorios del Dr. Esteve S.A.; EP2020230; (2009); (A1) English, View in Reaxys Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1902733; (2008); (A1) English, View in Reaxys Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.42

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

105.06

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

230

303/378

2017-11-11 00:22:14

1 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

δ 1.80-2.26(m, 8H); 2.04(s, 3H); 2.30(s 3H); 3.41(s, 2H); 6.89(dd, J=8.6, 1.5( Hz, 1H); 7.16(s, 1H); 7.22(d, J=8.6 H 1H); 7.29(s, 1H); 7.49(dd, J=8.7, 1.7 Hz, 1H); 7.90(d, J=1.7 Hz, 1H); 7.98(d, J=8.7 Hz, 1H); 10.13(bb, 1H) 10.93(s, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Comment (NMR Spectroscopy)

Signals given

Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys IR Spectroscopy (2) 1 of 2

Original Text (IR Spectroscopy)

2796, 1452, 1316, 1149, 1114, 1080, 1001, 810, 646, 559 1/cm

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 2 of 2

Patent; LABORATORIOS DEL DR. ESTEVE S.A.; WO2005/14000; (2005); (A1) English, View in Reaxys

Medchem (8) 1 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

304/378

2017-11-11 00:22:14

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Patent; Laboratorios del Dr. Esteve S.A.; EP2018861; (2009); (A1) English, View in Reaxys 2 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against human 5-hydroxytryptamine 6 receptor expressing HEK 293 cell line using [3H]-LSD as radioligand incubated at 37 degree C for 60 minutes

Biological Species/NCBI Human ID Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Measurement Parameter

Activity

Qualitative value

Concomitants: Compound name

[3H]LSD

Concomitants: Compound role

RAD

Patent; Vidal, Ramon Merce; Mataro, Blas Andaluz; Constansa, Jordi Frigola; US2005/65202; (2005); (A1) English, View in Reaxys 3 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Antagonist

Substance Effect

antagonistic activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Antagonistic activity of the compound towards human 5-Hydroxytryptamine 6 receptor expressed in HEK 293 cells using [3H]-LSD (2.7nM) as radioligand

Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Qualitative Results

Not Published

305/378

2017-11-11 00:22:14

4 of 8

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Merce-Vidal, Ramon; Andaluz-Mataro, Blas; Frigola-Constansa, Jordi; US2003/191124; (2003); (A1) English, View in Reaxys 5 of 8

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

6 of 8

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

306/378

2017-11-11 00:22:14

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

7 of 8

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human]

8 of 8

Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-hydroxytryptamine receptor 6 [human]

Target Synonyms

5-ht-6; 5-ht6; 5-hydroxytryptamine receptor 6; htr6; serotonin receptor 6

Target Uniprot ID

p50406

Target, Subunit, Species 5-hydroxytryptamine receptor 6 [human] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 6 [human]:Wild

307/378

2017-11-11 00:22:14

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cells/Cell Lines

HEK 293

Substance RN

14181097View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 22432088 View in Reaxys

147/181 CAS Registry Number: 1266605-82-6 Linear Structure Formula: C26H27F2N7O Molecular Formula: C26H27F2N7O Molecular Weight: 491.543 InChI Key: VNEDIPQYIHKWLB-WXTAPIANSA-N Note:

N N N

N N

OH N

Druglikeness (1) 1 of 1

LogP

2.35

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

260

308/378

2017-11-11 00:22:14

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

2.03

Measurement pX

3.29

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

2.03

Measurement pX

3.29

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

65.1

Measurement pX

1.79

309/378

2017-11-11 00:22:14

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

260

Measurement pX

1.19

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

4.07

Measurement pX

2.99

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432088View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

65.1

Measurement pX

1.79

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

310/378

2017-11-11 00:22:14

Reaxys ID 22432085 View in Reaxys

148/181

N N

OH N

CAS Registry Number: 1266605-80-4 Linear Structure Formula: C26H30F2N6O2 Molecular Formula: C26H30F2N6O2 Molecular Weight: 496.56 InChI Key: UAFYUKBSJYTLOY-WXTAPIANSA-N Note:

Druglikeness (1) 1 of 1

LogP

2.542

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

82.44

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

258

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.5

Measurement pX

3.9

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

311/378

2017-11-11 00:22:14

3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.5

Measurement pX

3.9

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

8.06

Measurement pX

2.7

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

129

Measurement pX

1.49

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

312/378

2017-11-11 00:22:14

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.5

Measurement pX

3.9

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432085View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

32.22

Measurement pX

2.09

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 11992643 View in Reaxys

149/181

CAS Registry Number: 731825-08-4 Chemical Name: 9-(4,5-dimethyl-thiazol-2-yl)-4-[4-(1H-indol-3ylmethyl)-piperazin-1-yl]-5,6,7,8-tetrahydro-1,3,4b-triaza-fluorene Linear Structure Formula: C28H31N7S Molecular Formula: C28H31N7S Molecular Weight: 497.667 InChI Key: OHSSKNYHOIZQRB-UHFFFAOYSA-N Note:

N N

N S

Substance Label (1) Label References 111

Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys Druglikeness (1)

313/378

2017-11-11 00:22:14

1 of 1

LogP

4.853

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

94.11

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Comment (NMR Spectroscopy)

Signals given

Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) DCI (Desorption chemical ionization)

References

Molecular peak

Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys

Medchem (1) 1 of 1

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : daunomycin accumulationTarget : COR.L23/R cells of humanBioassay : tritiated daunomycin, cytotoxic anthracycline medium; test compound concentration 10-5000nM; cells incubated at 37C for 2h

Substance RN

11992643View in Reaxys

Substance Name

111

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.3

Measurement pX

5.48

Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys

Reaxys ID 25760769 View in Reaxys

150/181 CAS Registry Number: 1349661-17-1 Linear Structure Formula: C28H31N7S Molecular Formula: C28H31N7S Molecular Weight: 497.667 InChI Key: AMOXTCKQRAEICA-UHFFFAOYSA-N Note:

N N N

N S

Druglikeness (1) 1 of 1

LogP

4.485

H Bond Donors

314/378

2017-11-11 00:22:14

H Bond Acceptors

Rotatable Bonds

TPSA

94.11

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

Multidrug resistance protein 1

Target Synonyms

abc transporter abcb.4; abc transporter b family member 4 (multidrug resistance protein 1); abcb1 (multidrug resistance protein 1); abcb1a; abcb4 (multidrug resistance protein 1); at2g47000; atabcb4; atp-binding cassette sub-family b member 1; atp-binding cassette sub-family b member 1a; ben1 (multidrug resistance protein 1); benomyl resistance protein 1; bmr (multidrug resistance protein 1); bmr1; bsu24010; cao19.13047; cao19.5604; f14m4.17; k08e7.9; mdr1 (multidrug resistance protein 1); mdr1a; mdr1b (multidrug resistance protein 1); mdr3 (multidrug resistance protein 1); mdr4 (multidrug resistance protein 1); mrp1 (multidrug resistance protein 1); multidrug resistance protein 1; multidrug resistance protein 1a; multidrug resistance protein 3 (multidrug resistance protein 1); multidrug resistance protein 4 (multidrug resistance protein 1); multidrug resistance protein pgp-1; multidrug-efflux transporter 1; p-glycoprotein (multidrug resistance protein 1); p-glycoprotein 1 (multidrug resistance protein 1); p-glycoprotein 3 (multidrug resistance protein 1); pglycoprotein 4; p-glycoprotein a; p-glycoprotein-related protein 1; pgp-1 (multidrug resistance protein 1); pgp1 (multidrug resistance protein 1); pgp4; pgy-3; pgy1 (multidrug resistance protein 1); pgy3 (multidrug resistance protein 1)

Target, Subunit, Species Multidrug resistance protein 1 Target Mutant/Chimera Details

Multidrug resistance protein 1:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against P-Glycoprotein

Substance RN

25760769View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys 2 of 2

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against daunomycin accumulation in COR.L23/R cells expressing multiple drug resistance protein after incubation at 37 degree C for 2 hours in a medium containing tritiated daunomycin (0.3 uCi/mL) and anthracycline

Biological Species/NCBI Human ID Cells/Cell Lines

COR-L23/R

Substance RN

25760769View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

3.3

Measurement pX

5.48

Patent; XENOVA LIMITED; WO2004/65389; (2004); (A1) English, View in Reaxys

315/378

2017-11-11 00:22:14

Reaxys ID 22432075 View in Reaxys

151/181

N N

OH N

CAS Registry Number: 1266605-75-7 Linear Structure Formula: C25H27ClF2N6O Molecular Formula: C25H27ClF2N6O Molecular Weight: 500.979 InChI Key: VMVQVNNCFZWQTK-CRICUBBOSA-N Note:

Druglikeness (1) 1 of 1

LogP

3.249

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

73.21

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

256

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

4.2

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

316/378

2017-11-11 00:22:14

3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

4.2

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

7.98

Measurement pX

2.7

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

63.88

Measurement pX

1.8

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

317/378

2017-11-11 00:22:14

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

4.2

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432075View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

31.94

Measurement pX

2.1

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 22432093 View in Reaxys

152/181 N

N N

CAS Registry Number: 1266605-81-5 Linear Structure Formula: C25H27F2N9O Molecular Formula: C25H27F2N9O Molecular Weight: 507.546 InChI Key: OOYHOUHWHUVJMQ-CRICUBBOSA-N Note:

N N

OH N

Druglikeness (1) 1 of 1

LogP

2.078

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

122.96

Lipinski Number

318/378

2017-11-11 00:22:14

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

252

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

4.2

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

4.2

319/378

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Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

3.94

Measurement pX

3.01

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

126

Measurement pX

1.5

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.25

Measurement pX

4.2

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

320/378

2017-11-11 00:22:14

7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432093View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

63.05

Measurement pX

1.8

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 25120863 View in Reaxys

153/181

O N

Linear Structure Formula: C25H22F6N4O Molecular Formula: C25H22F6N4O Molecular Weight: 508.466 InChI Key: CIFOCVBJYGFAPD-UHFFFAOYSA-N Note:

F F F

F F

Druglikeness (1) 1 of 1

LogP

4.584

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.13

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

5-Hydroxytryptamine 2A receptor

Target Synonyms

Target, Subunit, Species 5-Hydroxytryptamine 2A receptor Target Mutant/Chimera Details

5-Hydroxytryptamine 2A receptor:Wild

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro affinity of the compound towards 5-hydroxytryptamine 2A receptor

Substance RN

25120863View in Reaxys

321/378

2017-11-11 00:22:14

2 of 3

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Sodium-dependent serotonin transporter

Target Synonyms

Target, Subunit, Species Sodium-dependent serotonin transporter

3 of 3

Target Mutant/Chimera Details

Sodium-dependent serotonin transporter:Wild

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro affinity of the compound towards serotonin transporter

Substance RN

25120863View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

5-Hydroxytryptamine 1A receptor

Target Synonyms

Target, Subunit, Species 5-Hydroxytryptamine 1A receptor Target Mutant/Chimera Details

5-Hydroxytryptamine 1A receptor:Wild

Substance Action on Target

Radioligand (/ligand)

Substance Effect

binding activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro affinity of the compound towards 5-hydroxytryptamine 1A receptor using [3H]5-methoxy-3-(di-n-propylamino)chroman as radioligand

Substance RN

25120863View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Reaxys ID 26087883 View in Reaxys

154/181

322/378

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F O

F NH 2

F F

Linear Structure Formula: C2HF3O2*C23H27FN4O Molecular Formula: C2HF3O2*C23H27FN4O Molecular Weight: 508.516 InChI Key: XOJZRTVYJDAINI-FSRHSHDFSA-N Note:

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.66

Lipinski Number

Veber Number

Medchem (1) 1 of 1

Target Name

Dipeptidyl peptidase 4 [human]

Target Synonyms

adabp; adcp-2; adcp2; adenosine deaminase complexing protein 2; cd26; dipeptidyl peptidase 4; dipeptidyl peptidase iv; dpp iv; dpp4; t-cell activation antigen cd26; tp103

Target Uniprot ID

p27487

Target PDB ID

1j2e; 1n1m; 1nu6; 1nu8; 1pfq; 1r9m; 1r9n; 1rwq; 1tk3; 1tkr; 1u8e; 1w1i; 1wcy; 1x70; 2ajl; 2bgn; 2bgr; 2bub; 2fjp; 2g5p; 2g5t; 2g63; 2hha; 2i03; 2i78; 2iit; 2iiv; 2jid; 2oag; 2ogz; 2ole; 2onc; 2oph; 2oqi; 2oqv; 2p8s; 2qjr; 2qky; 2qoe; 2qt9; 2qtb; 2rgu; 2rip; 3bjm; 3c43; 3c45; 3ccb; 3ccc; 3d4l; 3eio; 3f8s; 3g0b; 3g0c; 3g0d; 3g0g; 3h0c; 3hab; 3hac; 3kwf; 3kwj; 3nox; 3o95; 3o9v; 3oc0; 3opm; 3q0t; 3q8w; 3qbj; 3sww; 3sx4; 3vjk; 3vjl; 3vjm; 3w2t; 4a5s; 4dsa; 4dsz; 4dtc; 4g1f; 4j3j; 4jh0; 4kr0; 4l72; 4lko; 4n8d; 4n8e; 4pnz; 4pv7; 4qzv

Target, Subunit, Species Dipeptidyl peptidase 4 [human] Target Mutant/Chimera Details

Dipeptidyl peptidase 4 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory constant of the compound against 50 pM human Dipeptidyl peptidase 4 upon incubation in 100 mM Hepes buffer, pH 7.5 for 30 min at 35 degree C using 50 uM Gly-ProAMC as substrate

Substance RN

26087883View in Reaxys

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

Measurement pX

Reaxys ID 20725055 View in Reaxys

155/181

323/378

2017-11-11 00:22:14

Linear Structure Formula: C29H28N6O3 Molecular Formula: C29H28N6O3 Molecular Weight: 508.58 InChI Key: ZCIAWRZDKXSETI-UHFFFAOYSA-N Note:

O NH

N N

Druglikeness (1) 1 of 1

LogP

1.528

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

101.64

Lipinski Number

Veber Number

Mass Spectrometry (1) Location References Page/Page column 97

Patent; MERCK SHARP andamp;; DOHME CORP.; STUMP, Craig, A.; QUIGLEY, Amy, G.; THEBERGE, Cory, R.; WOOD, Michael, R.; WO2010/107605; (2010); (A1) English, View in Reaxys

Reaxys ID 22432087 View in Reaxys

156/181 CAS Registry Number: 1266605-83-7 Linear Structure Formula: C26H29F2N7O2 Molecular Formula: C26H29F2N7O2 Molecular Weight: 509.559 InChI Key: XWNWLUXBJDZSEX-WXTAPIANSA-N Note:

OH N

N N

OH N

Druglikeness (1) 1 of 1

LogP

2.566

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

105.8

Lipinski Number

Veber Number

Medchem (5) 1 of 5

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antifungalMIC80: title compound concentration at which fungal growth was inhibited by 80 %

Biological Species/NCBI Cryptococcus neoformans ID Substance RN

22432087View in Reaxys

Substance Name

Measurement Parameter

MIC80

324/378

2017-11-11 00:22:14

Unit

Qualitative value

Quantitative value

251

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 5

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antifungalMIC80: title compound concentration at which fungal growth was inhibited by 80 %

Biological Species/NCBI Aspergillus fumigatus ID Substance RN

22432087View in Reaxys

Substance Name

Measurement Parameter

MIC80

Unit

Qualitative value

Quantitative value

251

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 5

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antifungalMIC80: title compound concentration at which fungal growth was inhibited by 80 %

Biological Species/NCBI Pichia kudriavzevii ID Substance RN

22432087View in Reaxys

Substance Name

Measurement Parameter

MIC80

Unit

Qualitative value

Quantitative value

251

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 5

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antifungalMIC80: title compound concentration at which fungal growth was inhibited by 80 %

Biological Species/NCBI Candida albicans ID Substance RN

22432087View in Reaxys

Substance Name

325/378

2017-11-11 00:22:14

Measurement Parameter

MIC80

Unit

Quantitative value

31.4

Measurement pX

2.11

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 5

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antifungalSpecies : Candida albicans ATCC MYA-1003 MIC80: title compound concentration at which fungal growth was inhibited by 80 %

Biological Species/NCBI Candida albicans ID Substance RN

22432087View in Reaxys

Substance Name

Measurement Parameter

MIC80

Unit

Qualitative value

Quantitative value

251

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 22432091 View in Reaxys

157/181 O N

N N

OH N

CAS Registry Number: 1266605-79-1 Linear Structure Formula: C25H27F2N7O3 Molecular Formula: C25H27F2N7O3 Molecular Weight: 511.531 InChI Key: FAGHMIXGHHCEPF-CRICUBBOSA-N Note:

Druglikeness (1) 1 of 1

LogP

2.519

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

119.03

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

326/378

2017-11-11 00:22:14

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

250

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.24

Measurement pX

4.22

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.24

Measurement pX

4.22

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

327/378

2017-11-11 00:22:14

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

3.91

Measurement pX

3.01

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

62.56

Measurement pX

1.81

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.24

Measurement pX

4.22

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

328/378

2017-11-11 00:22:14

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432091View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

7.82

Measurement pX

2.71

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 31558258 View in Reaxys HN O

158/181

O Z

Chemical Name: methyl (Z)-3-(((3-((4-methylpiperazin-1yl)methyl)-1H-indol-5-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate Linear Structure Formula: C31H31N5O3 Molecular Formula: C31H31N5O3 Molecular Weight: 521.619 InChI Key: XNLAEVVAFHZWEB-ZIADKAODSA-N Note:

H N

Substance Label (1) Label References A15

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.076

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

89.7

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

197.2 - 201.8

Solvent (Melting Point)

methanol

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy)

329/378

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, mass spectrome- Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum Medchem (3) 1 of 3

Target Name

Vascular endothelial growth factor receptor 2

Target Synonyms

ek1 (vascular endothelial growth factor receptor 2); endothelial kinase receptor ek1; fetal liver kinase 1 (vascular endothelial growth factor receptor 2); fetal liver kinase 1b; flk-1; flk-1b; flk1 (vascular endothelial growth factor receptor 2); flk1b; kdr (vascular endothelial growth factor receptor 2); kdrb; kinase insert domain receptor; kinase insert domain receptor-b; kinase nyk; protein-tyrosine kinase receptor flk-1 (vascular endothelial growth factor receptor 2); protein-tyrosine kinase receptor flk-1b; quek 1; quek1; si:busm1-205d10.1; si:ch211-254j6.1; vascular endothelial growth factor receptor 2; vascular endothelial growth factor receptor 2 homolog b; vegfr-2; vegfr-2 homolog b; vegfr2 (vascular endothelial growth factor receptor 2)

Target, Subunit, Species Vascular endothelial growth factor receptor 2 Target Mutant/Chimera Details

Vascular endothelial growth factor receptor 2:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

31558258View in Reaxys

Substance Name

methyl (Z)-3-(((3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

Substance Dose

1 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

6.16

330/378

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Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

A-549 cell line

Substance RN

31558258View in Reaxys

Substance Name

methyl (Z)-3-(((3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

Measurement Parameter

IC50

Unit

μM

Quantitative value

7.4

Measurement pX

5.13

Target Name

Platelet-derived growth factor receptor beta

Target Synonyms

beta platelet-derived growth factor receptor; beta-type platelet-derived growth factor receptor; cd140 antigen-like family member b; pdgf-r-beta; pdgfr (platelet-derived growth factor receptor beta); pdgfr-1; pdgfr-beta; pdgfr1; pdgfrb; platelet-derived growth factor receptor 1; platelet-derived growth factor receptor beta

Target, Subunit, Species Platelet-derived growth factor receptor beta Target Mutant/Chimera Details

Platelet-derived growth factor receptor beta:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

31558258View in Reaxys

Substance Name

methyl (Z)-3-(((3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate

Measurement Parameter

IC50

Unit

Quantitative value

135.1

Measurement pX

6.87

Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 - 502, View in Reaxys

Reaxys ID 12065107 View in Reaxys

159/181 Chemical Name: 1-(4-{5-[6-amino-5-(2,6-dichloro-benzyloxy)pyridin-3-yl]-1H-indol-3-ylmethyl}-piperazin-1-yl)-ethanone Linear Structure Formula: C27H27Cl2N5O2 Molecular Formula: C27H27Cl2N5O2 Molecular Weight: 524.45 InChI Key: OYACPHQVNCYSTD-UHFFFAOYSA-N Note:

N NH 2

HN O

Cl N O

Patent-Specific Data (1) References Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

331/378

2017-11-11 00:22:14

Druglikeness (1) 1 of 1

LogP

4.781

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

87.48

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCI3) 5 2.07 (s, 3H), 2.51 (m, 4H), 3.44 (m, 2H), 3.63 (m, 2H), 3.78 (S, 2H), 4.68 (br s, 2H), 5.40 (s, 2H), 7.17 (d, J = 2.2 Hz, 1H), 7.26 (m, 1H), 7.38 (m, 5H), 7.88 (S, 1H), 8.00 (d, = 1.8Hz, 1H), 8.34 (brs, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

Medchem (4) 1 of 4

Target Name

Hepatocyte growth factor receptor

Target Synonyms

hepatocyte growth factor receptor; hgf receptor; hgf/sf receptor; met (hepatocyte growth factor receptor); proto-oncogene c-met; scatter factor receptor; sf receptor; tyrosine-protein kinase met

Target, Subunit, Species Hepatocyte growth factor receptor Target Mutant/Chimera Details

Hepatocyte growth factor receptor:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

12065107View in Reaxys

Substance Name

I-68

Measurement Parameter

IC50

Unit

µM

Quantitative value

2.18

Measurement pX

5.66

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys 2 of 4

Target Name

protein kinase

Target Synonyms

protein kinase

Target, Subunit, Species protein kinase Target Mutant/Chimera Details

protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

332/378

2017-11-11 00:22:14

3 of 4

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Protein kinase was determined

Substance RN

12065107View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Hepatocyte growth factor receptor

Target Synonyms

hepatocyte growth factor receptor; hgf receptor; hgf/sf receptor; met (hepatocyte growth factor receptor); proto-oncogene c-met; scatter factor receptor; sf receptor; tyrosine-protein kinase met

Target, Subunit, Species Hepatocyte growth factor receptor

4 of 4

Target Mutant/Chimera Details

Hepatocyte growth factor receptor:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against MET using poly(glu-tyr) (4:1) as substrate at pH 7.4 (50 mM Hepes buffer) with compound dissolved in DMSO determined by Met transphosphorylation assay

Substance RN

12065107View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

2.18

Measurement pX

5.66

Target Name

protein kinase

Target Synonyms

protein kinase

Target, Subunit, Species protein kinase Target Mutant/Chimera Details

protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Protein kinase was determined

Substance RN

12065107View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

333/378

2017-11-11 00:22:14

Reaxys ID 12065459 View in Reaxys

160/181 Chemical Name: 1-(4-{5-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-1H-indol-3-ylmethyl}-piperazin-1-yl)-ethanone Linear Structure Formula: C27H26ClF2N5O2 Molecular Formula: C27H26ClF2N5O2 Molecular Weight: 525.986 InChI Key: IFALZBXDPWLSSQ-UHFFFAOYSA-N Note:

N NH 2

HN O

F N O

Cl F

Patent-Specific Data (1) References Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.481

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

87.48

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCI3) 6 2.08 (s, 3H), 2.49 (m, 4H), 3.48 (m, 2H), 3.61 (m, 2H), 3.80 (s, 2H), 4.68 (s, 2H), 5.30(s, 2H), 7.02 (m, 1H), 7.20 (m, 2H), 7.41 (m, 3H), 7.89(8,1H), 8.06 (s, 1H), 8.63 (S, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

Medchem (4) 1 of 4

Target Name

Hepatocyte growth factor receptor

Target Synonyms

hepatocyte growth factor receptor; hgf receptor; hgf/sf receptor; met (hepatocyte growth factor receptor); proto-oncogene c-met; scatter factor receptor; sf receptor; tyrosine-protein kinase met

Target, Subunit, Species Hepatocyte growth factor receptor Target Mutant/Chimera Details

Hepatocyte growth factor receptor:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

12065459View in Reaxys

Substance Name

I-70

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.8

334/378

2017-11-11 00:22:14

Measurement pX

6.1

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys 2 of 4

Target Name

protein kinase

Target Synonyms

protein kinase

Target, Subunit, Species protein kinase

3 of 4

Target Mutant/Chimera Details

protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Protein kinase was determined

Substance RN

12065459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Hepatocyte growth factor receptor

Target Synonyms

hepatocyte growth factor receptor; hgf receptor; hgf/sf receptor; met (hepatocyte growth factor receptor); proto-oncogene c-met; scatter factor receptor; sf receptor; tyrosine-protein kinase met

Target, Subunit, Species Hepatocyte growth factor receptor

4 of 4

Target Mutant/Chimera Details

Hepatocyte growth factor receptor:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against MET using poly(glu-tyr) (4:1) as substrate at pH 7.4 (50 mM Hepes buffer) with compound dissolved in DMSO determined by Met transphosphorylation assay

Substance RN

12065459View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.8

Measurement pX

6.1

Target Name

protein kinase

Target Synonyms

protein kinase

Target, Subunit, Species protein kinase Target Mutant/Chimera Details

protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

335/378

2017-11-11 00:22:14

Bioassay Details

Inhibitory activity of the compound against Protein kinase was determined

Substance RN

12065459View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

Reaxys ID 12065502 View in Reaxys

161/181 Chemical Name: 1-(4-{5-[5-amino-6-(2-chloro-3,6-difluoro-benzyloxy)-pyrazin-2-yl]-1H-indol-3-ylmethyl}-piperazin-1-yl)-ethanone Linear Structure Formula: C26H25ClF2N6O2 Molecular Formula: C26H25ClF2N6O2 Molecular Weight: 526.973 InChI Key: WREGOQQTMQTCDW-UHFFFAOYSA-N Note:

F HN

O N

F N

NH 2

Patent-Specific Data (1) References Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

4.046

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

100.37

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCI3) 6 2.08 (s, 3H), 2.55 (m, 4H), 3.45 (m, 2H), 3.64(m, 2H), 3.81 (s, 2H), 4.78 (s, 2H), 5.71(s, 2H), 7.08 (m, 1H), 7.18 (m, 2H), 7.31 (d, 1H), 7.79(d, 1H), 8.04 (s, 1H), 8.22 (s, 1H), 8.49(s, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

Medchem (4) 1 of 4

Target Name

Hepatocyte growth factor receptor

Target Synonyms

hepatocyte growth factor receptor; hgf receptor; hgf/sf receptor; met (hepatocyte growth factor receptor); proto-oncogene c-met; scatter factor receptor; sf receptor; tyrosine-protein kinase met

Target, Subunit, Species Hepatocyte growth factor receptor

336/378

2017-11-11 00:22:14

Target Mutant/Chimera Details

Hepatocyte growth factor receptor:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

12065502View in Reaxys

Substance Name

II-64

Measurement Parameter

IC50

Unit

µM

Quantitative value

1.5

Measurement pX

5.82

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys 2 of 4

Target Name

protein kinase

Target Synonyms

protein kinase

Target, Subunit, Species protein kinase

3 of 4

Target Mutant/Chimera Details

protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Protein kinase was determined

Substance RN

12065502View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Target Name

Hepatocyte growth factor receptor

Target Synonyms

hepatocyte growth factor receptor; hgf receptor; hgf/sf receptor; met (hepatocyte growth factor receptor); proto-oncogene c-met; scatter factor receptor; sf receptor; tyrosine-protein kinase met

Target, Subunit, Species Hepatocyte growth factor receptor Target Mutant/Chimera Details

Hepatocyte growth factor receptor:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against MET using poly(glu-tyr) (4:1) as substrate at pH 7.4 (50 mM Hepes buffer) with compound dissolved in DMSO determined by Met transphosphorylation assay

Substance RN

12065502View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

1.5

337/378

2017-11-11 00:22:14

4 of 4

Measurement pX

5.82

Target Name

protein kinase

Target Synonyms

protein kinase

Target, Subunit, Species protein kinase Target Mutant/Chimera Details

protein kinase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of the compound against Protein kinase was determined

Substance RN

12065502View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; SUGEN, INC.; WO2004/76412; (2004); (A2) English, View in Reaxys

Reaxys ID 26194769 View in Reaxys

162/181 Linear Structure Formula: C28H30F2N6O3 Molecular Formula: C28H30F2N6O3 Molecular Weight: 536.581 InChI Key: BYDDVYPSKQEEAJ-UQDIGLKLSA-N Note:

N N F

N E

Druglikeness (1) 1 of 1

LogP

2.514

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

110.51

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

338/378

2017-11-11 00:22:14

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

239

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

119

Measurement pX

1.53

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

119

Measurement pX

1.53

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

339/378

2017-11-11 00:22:14

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

239

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

239

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

119

Measurement pX

1.53

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

26194769View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

340/378

2017-11-11 00:22:14

Qualitative value

Quantitative value

239

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 22432082 View in Reaxys

163/181

N N

OH N

CAS Registry Number: 1266605-76-8 Linear Structure Formula: C25H27BrF2N6O Molecular Formula: C25H27BrF2N6O Molecular Weight: 545.43 InChI Key: IQNKQOUNDLEETD-CRICUBBOSA-N Note:

Druglikeness (1) 1 of 1

LogP

3.425

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

73.21

Lipinski Number

Veber Number

Medchem (7) 1 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Cryptococcus neoformans ATCC 36556 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Cryptococcus neoformans ATCC 36556 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

235

Measurement pX

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 2 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 90028 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

341/378

2017-11-11 00:22:14

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.23

Measurement pX

4.24

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 3 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 36082 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 36082 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.23

Measurement pX

4.24

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 4 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida krusei ATCC 6258 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Pichia kudriavzevii ATCC 6258 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

1.83

Measurement pX

3.34

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 5 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC MYA-1003 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC MYA-1003 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

342/378

2017-11-11 00:22:14

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

29.34

Measurement pX

2.14

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 6 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Candida albicans ATCC 64548 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Candida albicans ATCC 64548 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

0.23

Measurement pX

4.24

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys 7 of 7

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro minimum inhibitory concentration of compound against Aspergillus fumigatus ATCC 16424 upon incubation for 72 hour by Micro-plate reader assay

Biological Species/NCBI Aspergillus fumigatus ATCC 16424 ID Substance RN

22432082View in Reaxys

Measurement Parameter

MIC80

Unit

µmol/mL

Measurement Object

Growth inhibition

Qualitative value

Quantitative value

7.33

Measurement pX

2.74

Na, Young Min; Bulletin of the Korean Chemical Society; vol. 31; nb. 11; (2010); p. 3467 - 3470, View in Reaxys

Reaxys ID 28817958 View in Reaxys

164/181

343/378

2017-11-11 00:22:14

Chemical Name: N-(2-(4-((1H-indol-3-yl)methyl)piperazin-1yl)-5-(trifluoromethyl)phenyl)-5-(pyridin-4-yl)furan-2-carboxamide Linear Structure Formula: C30H26F3N5O2 Molecular Formula: C30H26F3N5O2 Molecular Weight: 545.564 InChI Key: PXTGGKHRMSAKSB-UHFFFAOYSA-N Note:

N H

N N NH

Substance Label (2) Label References 74

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Patent; THE UNIVERSITY OF NOTTINGHAM; NEWSOUTH INNOVATIONS PTY LIMITED; BATES, David; MORRIS, Jonathan; WO2015/159103; (2015); (A1) English, View in Reaxys

Patent-Specific Data (2) References Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys Patent; THE UNIVERSITY OF NOTTINGHAM; NEWSOUTH INNOVATIONS PTY LIMITED; BATES, David; MORRIS, Jonathan; WO2015/159103; (2015); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

5.109

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

77.4

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

Page/Page column 55

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

‘H NMR (300 MHz; CDC13) 6 2.82 (br s, 4H), 2.97 (m, 4H),3.82 (s, 2H), 7.06 (d, J 3.7 Hz, 1H), 7.08-7.13 (m, 2H), 7.17-7.23 (m, 1H), 7.30 (d, J = 8.2 Hz, 111), 7.3 5-7.40 (m, 3H),

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7.72 (d, J= 8.0 Hz, 111), 7.75-7,77 (m, 2H), 8.30 (s, 1H), 8.78-8.80 (m, 211), 8.86 (d, J= 1.8 Hz, 111), 9.68 (s, 111). Location

Page/Page column 55

Patent; THE UNIVERSITY OF NOTTINGHAM; NEWSOUTH INNOVATIONS PTY LIMITED; BATES, David; MORRIS, Jonathan; WO2015/159103; (2015); (A1) English, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Page/Page column 55

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

electrospray ionisation (ESI); high resolution mass spectrometry (HRMS); spectrum

Page/Page column 55

Patent; THE UNIVERSITY OF NOTTINGHAM; NEWSOUTH INNOVATIONS PTY LIMITED; BATES, David; MORRIS, Jonathan; WO2015/159103; (2015); (A1) English, View in Reaxys

Medchem (2) 1 of 2

Target Name

SRSF protein kinase 1

Target Synonyms

serine/arginine-rich protein-specific kinase 1; sfrs protein kinase 1; sr-protein-specific kinase 1; srpk1 (srsf protein kinase 1); srsf protein kinase 1

Target, Subunit, Species SRSF protein kinase 1 Target Mutant/Chimera Details

SRSF protein kinase 1:Wild

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

28817958View in Reaxys

Measurement Parameter

IC50

Unit

Quantitative value

164

Measurement pX

6.79

Patent; THE UNIVERSITY OF NOTTINGHAM; NEWSOUTH INNOVATIONS PTY LIMITED; BATES, David; MORRIS, Jonathan; WO2015/159103; (2015); (A1) English, View in Reaxys 2 of 2

Target Name

Probable serine/threonine-protein kinase sky1

Target Synonyms

ddb_g0275627; probable serine/threonine-protein kinase sky1; sky1 (probable serine/ threonine-protein kinase sky1); srpk1-like kinase

Target, Subunit, Species Probable serine/threonine-protein kinase sky1 Target Mutant/Chimera Details

Probable serine/threonine-protein kinase sky1:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

28817958View in Reaxys

Substance Name

N-(2-(4-((1H-indol-3-yl)methyl)piperazin-1-yl)-5-(trifluoromethyl)phenyl)-5-(pyridin-4-yl)furan-2-carboxamide

Measurement Parameter

IC50

345/378

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Unit

Quantitative value

164.4

Measurement pX

6.79

Patent; EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer; (83 pag.); WO2017/64512; (2017); (A1) English, View in Reaxys

Reaxys ID 12251232 View in Reaxys

165/181 Chemical Name: 3-{4-[[1-(2,6-dimethylphenyl)-1H-tetrazol-5yl]-(3-trifluoromethylphenyl)methyl]piperazin-1-ylmethyl}-1H-indole Linear Structure Formula: C30H30F3N7 Molecular Formula: C30H30F3N7 Molecular Weight: 545.61 InChI Key: CKAZCJFSWDKTAZ-UHFFFAOYSA-N Note:

F HN

F N

N N

Substance Label (1) Label References 150

Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys

Patent-Specific Data (1) References Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

5.95

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

65.87

Lipinski Number

Veber Number

Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys

Medchem (4) 1 of 4

Target Name

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

p97639

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [Rattus norvegicus] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Antagonist

Bioassay Category

In Vitro (Efficacy)

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Bioassay Name

Ca2+ mobilisation

Cells/Cell Lines

CHO-K1

Substance RN

12251232View in Reaxys

Substance Name

150

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

2815775

Concomitants: Compound name

Probenecid; [Fura-2]

Concomitants: Compound role

COM; MAR

Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys 2 of 4

Target Name

Melanin-concentrating hormone receptor 1 [human]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

q99705

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [human] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Antagonist

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Ca2+ mobilisation

Cells/Cell Lines

CHO-K1

Substance RN

12251232View in Reaxys

Substance Name

150

Measurement Parameter

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

2815775

Concomitants: Compound name

Probenecid; [Fura-2]

Concomitants: Compound role

COM; MAR

Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys

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3 of 4

Target Name

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

p97639

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [Rattus norvegicus] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

12251232View in Reaxys

Substance Name

150

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

5368869; 2835835

Concomitants: Compound name

Phosphoramidon; Pefabloc; Trypsin inhibitor

Concomitants: Compound role

COM; COM; COM

Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys 4 of 4

Target Name

Melanin-concentrating hormone receptor 1 [human]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

q99705

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [human] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

12251232View in Reaxys

Substance Name

150

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Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

5368869; 2835835

Concomitants: Compound name

Phosphoramidon; Pefabloc; Trypsin inhibitor

Concomitants: Compound role

COM; COM; COM

Patent; AMGEN, INC.; WO2005/19167; (2005); (A2) English, View in Reaxys

Reaxys ID 25024367 View in Reaxys

166/181 Linear Structure Formula: C30H30F3N7 Molecular Formula: C30H30F3N7 Molecular Weight: 545.61 InChI Key: CKAZCJFSWDKTAZ-NDEPHWFRSA-N Note:

HN N N

F F F

Druglikeness (1) 1 of 1

LogP

5.95

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

65.87

Lipinski Number

Veber Number

Medchem (5) 1 of 5

Target Name

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

p97639

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [Rattus norvegicus] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

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2 of 5

Bioassay Details

In vitro inhibition against rat Melanin-concentrating hormone receptor 1 mediated intracellular calcium response in CHOK1-Gqi cells detected using FLIPR

Cells/Cell Lines

CHO-K1-GQI

Substance RN

25024367View in Reaxys

Measurement Parameter

Unit

µM

Measurement Object

Melanin-concentrating hormone receptor 1 mediated intracellular calcium response in CHO1-Gqi cells

Qualitative value

Quantitative value

100

Measurement pX

Target Name

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

p97639

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [Rattus norvegicus]

3 of 5

Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition against rat Melanin-concentrating hormone receptor 1 mediated intracellular calcium response in HEK 293 cells

Cells/Cell Lines

HEK 293

Substance RN

25024367View in Reaxys

Measurement Parameter

Unit

µM

Measurement Object

Melanin-concentrating hormone receptor 1 mediated intracellular calcium response in HEK 293 cells

Qualitative value

Quantitative value

Measurement pX

Target Name

Melanin-concentrating hormone receptor 1 [human]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

q99705

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [human] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [human]:Wild

Target Species (Bioactivity)

human

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4 of 5

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition against 0.2 nM 125I native-MCH binding to human Melanin concentrating hormone receptor 1 expressed in HEK 293 cells after incubation at 30 degree C for 90 min

Cells/Cell Lines

HEK 293

Substance RN

25024367View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Target Name

Melanin-concentrating hormone receptor 1 [human]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

q99705

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [human]

5 of 5

Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition against human Melanin-concentrating hormone receptor 1 mediated intracellular calcium response in CHOK1-Gqi cells detected using FLIPR

Cells/Cell Lines

CHO-K1-GQI

Substance RN

25024367View in Reaxys

Measurement Parameter

Unit

µM

Measurement Object

inhibition against human Melanin-concentrating hormone receptor 1

Qualitative value

Quantitative value

100

Measurement pX

Target Name

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]

Target Synonyms

g-protein coupled receptor 24; gpr24; mch receptor 1; mch-1r; mch-r1; mch1r; mchr; mchr-1; mchr1; melanin-concentrating hormone receptor 1; slc-1; slc1; somatostatin receptor-like protein

Target Uniprot ID

p97639

Target, Subunit, Species Melanin-concentrating hormone receptor 1 [Rattus norvegicus] Target Mutant/Chimera Details

Melanin-concentrating hormone receptor 1 [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

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Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition against 0.2 nM 125I native-MCH binding to rat Melanin concentrating hormone receptor 1 expressed in HEK 293 cells after incubation at 30 degree C for 90 min

Cells/Cell Lines

HEK 293

Substance RN

25024367View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Reaxys ID 22981168 View in Reaxys O

CAS Registry Number: 1403360-01-9 Linear Structure Formula: C27H27F3N6O4 Molecular Formula: C27H27F3N6O4 Molecular Weight: 556.544 InChI Key: PRQPTJGEDHERPW-UHFFFAOYSA-N Note:

N O

167/181

N N

F F

Patent-Specific Data (1) References Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAWANO, Yoshikazu; HARAGUCHI, Yoshikazu; SASAKI, Hirofumi; UEMATSU, Yukitaka; TSUBOUCHI, Hidetsugu; YATA, Hiromi; SHIMIZU, Hiroshi; KOHASHI, Kazuho; ITOTANI, Motohiro; TAI, Kuninori; TAKEMURA, Isao; HAYASHI, Mikayo; HASHIZUME, Hiroyuki; MATSUBA, Miki; NAKAMURA, Izuru; CHEN, Xiuhao; MATSUMOTO, Makoto; WO2012/141338; (2012); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

6.996

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

104.37

Lipinski Number

Veber Number

Mass Spectrometry (1) Location References Page/Page column 346

Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAWANO, Yoshikazu; HARAGUCHI, Yoshikazu; SASAKI, Hirofumi; UEMATSU, Yukitaka; TSUBOUCHI, Hidetsugu; YATA, Hiromi; SHIMIZU, Hiroshi; KOHASHI, Kazuho; ITOTANI, Motohiro; TAI, Kuninori; TAKEMURA, Isao; HAYASHI, Mikayo; HASHIZUME, Hiroyuki; MATSUBA, Miki; NAKAMURA, Izuru; CHEN, Xiuhao; MATSUMOTO, Makoto; WO2012/141338; (2012); (A1) English, View in Reaxys

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Reaxys ID 380252 View in Reaxys

168/181 CAS Registry Number: 103401-68-9 Chemical Name: 1,4-bis-(5-benzyloxy-indol-3-ylmethyl)-piperazine; 1,4-Bis-(5-benzyloxy-indol-3-ylmethyl)-piperazin Linear Structure Formula: C36H36N4O2 Molecular Formula: C36H36N4O2 Molecular Weight: 556.707 Type of Substance: heterocyclic InChI Key: CGCRHVIYJGBKHL-UHFFFAOYSA-N Note:

NH O N

N O HN

Druglikeness (1) 1 of 1

LogP

6.592

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

56.52

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

229 - 230

Solvent (Melting Point)

dimethylformamide

Koo et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 179,183, View in Reaxys

Reaxys ID 27604342 View in Reaxys

169/181 Chemical Name: 4-{4-[(4-((1H-indol-3-yl)methyl)piperazin-1yl)methyl]-1H-1,2,3-triazol-1-yl}-2,8-bis(trifluoromethyl)quinoline Linear Structure Formula: C27H23F6N7 Molecular Formula: C27H23F6N7 Molecular Weight: 559.517 InChI Key: MPXYFBKYQYXTLZ-UHFFFAOYSA-N Note:

N N

F F N

F F

Substance Label (1) Label References 23

Druglikeness (1) 1 of 1

LogP

4.793

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

65.87

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

92 - 93

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Solvent (Melting Point)

neat (no solvent, solid phase)

Location

supporting information

Crystal Property Description (1) Colour & Other Location Properties brown

supporting information

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

75.5

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

282

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Location

supporting information

Description (IR Spectroscopy)

ATR (attenuated total reflectance); Intensity of IR bands; Bands

Location

supporting information

Hamann, Anton R.; De Kock, Carmen; Smith, Peter J.; Van Otterlo, Willem A.L.; Blackie, Margaret A.L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 23; (2014); p. 5466 - 5469, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

References

supporting information

Medchem (1) 1 of 1

Substance Effect

Antiplasmodic

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration of compound against growth of PLASMODIUM FALCIPARUM NF54, CHLOROQUINE-SUSCEPTIBLE upon incubation at RT for 24 hrs

Biological Species/NCBI chloroquine susceptible Plasmodium falciparum NF54 ID Substance RN

27604342View in Reaxys

Measurement Parameter

IC50

Unit

µg/mL

Measurement Object

PARASITE GROWTH

Qualitative value

Quantitative value

0.708

Measurement pX

5.9

Reaxys ID 12637634 View in Reaxys

170/181

O N O

N N

Linear Structure Formula: C31H40FN7O2 Molecular Formula: C31H40FN7O2 Molecular Weight: 561.703 InChI Key: QXDUUKULQWPOKB-UHFFFAOYSA-N Note:

N F

Substance Label (1) Label References Final compound 129

Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/67139; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/67139; (2006); (A1) English, View in Reaxys Druglikeness (1)

355/378

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1 of 1

LogP

3.662

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

70.65

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

Alpha-2A adrenergic receptor [human]

Target Synonyms

adra2a; adra2r; adrar; alpha-2 adrenergic receptor subtype c10; alpha-2a adrenergic receptor; alpha-2a adrenoceptor; alpha-2a adrenoreceptor; alpha-2aar

Target Uniprot ID

p08913

Target, Subunit, Species Alpha-2A adrenergic receptor [human] Target Mutant/Chimera Details

Alpha-2A adrenergic receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

12637634View in Reaxys

Substance Name

129

Substance Dose

1.00000E-09 M

Measurement Parameter

pIC50

Quantitative value

7.3

Measurement pX

7.3

Concomitants: Compound RN

886303; 97277

Concomitants: Compound name

Oxymetazoline; [3H]-Rauwolscine

Concomitants: Compound role

NSB; RAD

Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/67139; (2006); (A1) English, View in Reaxys 2 of 2

Target Name

Alpha-2C adrenergic receptor [human]

Target Synonyms

adra2c; adra2l2; adra2rl2; alpha-2 adrenergic receptor subtype c4; alpha-2c adrenergic receptor; alpha-2c adrenoceptor; alpha-2c adrenoreceptor; alpha-2car

Target Uniprot ID

p18825

Target, Subunit, Species Alpha-2C adrenergic receptor [human] Target Mutant/Chimera Details

Alpha-2C adrenergic receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

356/378

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Bioassay Name

Binding

Cells/Cell Lines

CHO

Cell Fraction

Membrane

Substance RN

12637634View in Reaxys

Substance Name

129

Substance Dose

1.00000E-09 M

Measurement Parameter

pIC50

Quantitative value

8.7

Measurement pX

8.7

Concomitants: Compound RN

97277

Concomitants: Compound name

[3H]-Rauwolscine; Spiroxatrine

Concomitants: Compound role

RAD; NSB

Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/67139; (2006); (A1) English, View in Reaxys

Reaxys ID 14142573 View in Reaxys

171/181 CAS Registry Number: 273726-92-4 Chemical Name: 4'-Trifluoromethyl-biphenyl-2-carboxylic acid {4-[4-(5-fluoro-1H-indol-3-ylmethyl)-piperazin-1-yl]-phenyl}amide Linear Structure Formula: C33H28F4N4O Molecular Formula: C33H28F4N4O Molecular Weight: 572.605 InChI Key: FOZRZYXMBRQARJ-UHFFFAOYSA-N Note:

F F

F N N HN

NH O

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Claim

Patent; SmithKline Beecham Corporation; US6552022; (2003); (B1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

7.809

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

51.37

Lipinski Number

Veber Number

Reaxys ID 5217660 View in Reaxys

172/181

357/378

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CAS Registry Number: 75410-87-6 Linear Structure Formula: C22H22N4*2C4H4O4 Molecular Formula: 2C4H4O4*C22H22N4 Molecular Weight: 574.59 Type of Substance: heterocyclic InChI Key: UCVXLJPWDABHAA-BTJKTKAUSA-N Note:

2 O

OH NH

N N

Substance Label (1) Label References IVa-dimaleate

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

109.76

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

132 - 134

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

5217660View in Reaxys

Substance Name

IVa-dimaleate

Qualitative Results

active on the central seretoninergic system, and possesses a number of properties typical of the tricyclic antidepressants

Measurement Parameter

Qualitative

Reaxys ID 22690421 View in Reaxys

173/181 Chemical Name: D-429; 6-({2-[4-(1H-indol-3-ylmethyl)piperazin-1-yl]ethyl}propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol tetrahydrochloride Linear Structure Formula: C28H38N4O*4ClH Molecular Formula: C28H38N4O*4ClH Molecular Weight: 592.48 InChI Key: BFOCHSDORYDSCA-UHFFFAOYSA-N Note:

OH 4

N N

HCl

Druglikeness (1) 1 of 1

LogP

4.373

H Bond Donors

358/378

2017-11-11 00:22:14

H Bond Acceptors

Rotatable Bonds

TPSA

45.74

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

180 - 185

Solvent (Melting Point)

water

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys Medchem (2) 1 of 2

Target Name

Dopamine 2 long receptor [Rattus norvegicus]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [Rattus norvegicus] Target Mutant/Chimera Details

Dopamine 2 long receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

22690421View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

82.1

Deviation

7.10000

Measurement pX

7.09

Concomitants: Compound RN

632204; 1551655; 84272

Concomitants: Compound name

[3H]-Spiperone; (+)-Butaclamol; L-(+)-Ascorbic acid

Concomitants: Compound role

RAD; NSB; COM

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys 2 of 2

Target Name

D(3) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p19020

Target, Subunit, Species D(3) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(3) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

359/378

2017-11-11 00:22:14

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

HEK 293

Cell Fraction

Membrane

Substance RN

22690421View in Reaxys

Substance Name

Measurement Parameter

Unit

Quantitative value

3.2

Deviation

0.320000

Measurement pX

8.49

Concomitants: Compound RN

632204; 1551655; 84272

Concomitants: Compound name

[3H]-Spiperone; (+)-Butaclamol; L-(+)-Ascorbic acid

Concomitants: Compound role

RAD; NSB; COM

Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 55; nb. 12; (2012); p. 5826 - 5840, View in Reaxys

Reaxys ID 12462459 View in Reaxys

174/181 Linear Structure Formula: C33H33N9OS Molecular Formula: C33H33N9OS Molecular Weight: 603.751 InChI Key: DFIWUWMJFIQXAV-UHFFFAOYSA-N Note:

N N H 2N

N N

Patent-Specific Data (1) References Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/105778; (2005); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

3.06

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

165.15

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

360/378

2017-11-11 00:22:14

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Molecular peak

Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/105778; (2005); (A2) English, View in Reaxys

Reaxys ID 26222075 View in Reaxys

175/181 Linear Structure Formula: C36H49N7O4 Molecular Formula: C36H49N7O4 Molecular Weight: 643.83 InChI Key: KQWBTESXIVPLNI-CLTPBEKXSA-N Note:

HN O

H N

H 2N O

N H

N N

Druglikeness (1) 1 of 1

LogP

3.901

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

148.58

Lipinski Number

Veber Number

Medchem (5) 1 of 5

Target Name

Somatostatin receptor type 3 [human]

Target Synonyms

somatostatin receptor type 3; ss-3-r; ss3-r; ss3r; ssr-28; sstr3

Target Uniprot ID

p32745

Target, Subunit, Species Somatostatin receptor type 3 [human] Target Mutant/Chimera Details

Somatostatin receptor type 3 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against binding of [125I]Try11 Somatostatin to human somatostatin receptor type 3 in CHO-K1 cells upon incubation at 25 degree C for 30 minutes; Range is 30 pM to 3 uM

Biological Species/NCBI Human ID Cells/Cell Lines

CHO-K1

Substance RN

26222075View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

361/378

2017-11-11 00:22:14

2 of 5

Quantitative value

Measurement pX

5.52

Concomitants: Compound name

[125I]Tyr11 Somatostatin

Concomitants: Compound role

RAD

Target Name

Somatostatin receptor type 4 [human]

Target Synonyms

somatostatin receptor type 4; ss-4-r; ss4-r; ss4r; sstr4

Target Uniprot ID

p31391

Target, Subunit, Species Somatostatin receptor type 4 [human] Target Mutant/Chimera Details

Somatostatin receptor type 4 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against binding of [125I]Try11 somatostatin to human somatostatin receptor type 4 in CHO-K1 cells upon incubation at 25 degree C for 30 minutes, pH 7.8; Range is 30 pM to 3 uM

Biological Species/NCBI Human ID

3 of 5

Cells/Cell Lines

CHO-K1

Substance RN

26222075View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

5.52

Concomitants: Compound name

[125I]Tyr11 Somatostatin

Concomitants: Compound role

RAD

Target Name

Somatostatin receptor type 5 [human]

Target Synonyms

somatostatin receptor type 5; ss-5-r; ss5-r; ss5r; sstr5

Target Uniprot ID

p35346

Target, Subunit, Species Somatostatin receptor type 5 [human] Target Mutant/Chimera Details

Somatostatin receptor type 5 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against binding of [125I]Try11 Somatostatin to human somatostatin receptor type 5 in CHO-K1 cells upon incubation at 25 degree C for 30 minutes, pH 7.8; Range is 30 pM to 3 uM

362/378

2017-11-11 00:22:14

Biological Species/NCBI Human ID

4 of 5

Cells/Cell Lines

CHO-K1

Substance RN

26222075View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

5.52

Concomitants: Compound name

[125I]Tyr11 Somatostatin

Concomitants: Compound role

RAD

Target Name

Somatostatin receptor type 1 [human]

Target Synonyms

somatostatin receptor type 1; srif-2; ss-1-r; ss1-r; ss1r; sstr1

Target Uniprot ID

p30872

Target, Subunit, Species Somatostatin receptor type 1 [human] Target Mutant/Chimera Details

Somatostatin receptor type 1 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against binding of [125I]Try11 Somatostatin to human somatostatin receptor type 1 in CHO-K1 cells upon incubation at 25 degree C for 30 minutes; Range is 30 pM to 3 uM

Biological Species/NCBI Human ID

5 of 5

Cells/Cell Lines

CHO-K1

Substance RN

26222075View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

5.52

Concomitants: Compound name

[125I]Tyr11 Somatostatin

Concomitants: Compound role

RAD

Target Name

Somatostatin receptor type 2 [human]

Target Synonyms

somatostatin receptor type 2; srif-1; ss-2-r; ss2-r; ss2r; sstr2

Target Uniprot ID

p30874; p30874-1

Target, Subunit, Species Somatostatin receptor type 2 [human] Target Mutant/Chimera Details

Somatostatin receptor type 2 [human]:Wild

363/378

2017-11-11 00:22:14

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration against binding of [125I]Try11 Somatostatin to human somatostatin receptor type 2 in CHO-K1 cells upon incubation at 25 degree C for 30 minutes; Range is 30 pM to 3 uM

Biological Species/NCBI Human ID Cells/Cell Lines

CHO-K1

Substance RN

26222075View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

Measurement pX

5.52

Concomitants: Compound name

[125I]Tyr11 Somatostatin

Concomitants: Compound role

RAD

Reaxys ID 28884180 View in Reaxys

176/181

F 3 F N

H 2N S

OH F

Chemical Name: N6-(2-(4-((5-fluoro-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine trifluoroacetic acid Linear Structure Formula: C25H35FN6S*3C2HF3O2 Molecular Formula: 3C2HF3O2*C25H35FN6S Molecular Weight: 812.729 InChI Key: JRYRIQZLHDAUMS-UHFFFAOYSA-N Note:

Substance Label (1) Label References 14a

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

129.96

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Location data

References

HPLC (High performance liquid chromatography)

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

supporting information

364/378

2017-11-11 00:22:14

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); spectrum

References Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Medchem (3) 1 of 3

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Substance RN

28884180View in Reaxys

Substance Name

N%6&-(2-(4-((5-fluoro-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N%6&-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine trifluoroacetic acid

Substance Dose

0 - 250 μM

Measurement Parameter

% Reduction

Qualitative value

Active

Target Name

D(3) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p19020

Target, Subunit, Species D(3) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(3) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

28884180View in Reaxys

Substance Name

N%6&-(2-(4-((5-fluoro-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N%6&-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine trifluoroacetic acid

Measurement Parameter

Unit

Quantitative value

12.1

365/378

2017-11-11 00:22:14

Measurement pX

7.92

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-spiroperidol

Concomitants: Compound role

RAD

Target Name

Dopamine 2 long receptor [Rattus norvegicus]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [Rattus norvegicus] Target Mutant/Chimera Details

Dopamine 2 long receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

28884180View in Reaxys

Substance Name

N%6&-(2-(4-((5-fluoro-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N%6&-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine trifluoroacetic acid

Measurement Parameter

Unit

Quantitative value

854

Measurement pX

6.07

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-spiroperidol

Concomitants: Compound role

RAD

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Reaxys ID 28884191 View in Reaxys

177/181

O O

3 F F

H 2N S

OH F

Chemical Name: N6-(2-(4-((5-methoxy-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine Linear Structure Formula: C26H38N6OS*3C2HF3O2 Molecular Formula: 3C2HF3O2*C26H38N6OS Molecular Weight: 824.765 InChI Key: PWNHFSBIYOLUKO-UHFFFAOYSA-N Note:

Substance Label (1) Label References

366/378

2017-11-11 00:22:14

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

139.19

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Location data

References

HPLC (High performance liquid chromatography)

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

supporting information

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

600

Medchem (3) 1 of 3

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Substance RN

28884191View in Reaxys

Substance Name

N%6&-(2-(4-((5-methoxy-1H-indol-3-yl)methyl)-piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine

Substance Dose

0 - 250 μM

Measurement Parameter

% Reduction

Qualitative value

Active

Target Name

D(3) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p19020

Target, Subunit, Species D(3) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(3) dopamine receptor [Rattus norvegicus]:Wild

367/378

2017-11-11 00:22:14

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

28884191View in Reaxys

Substance Name

N%6&-(2-(4-((5-methoxy-1H-indol-3-yl)methyl)-piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine

Measurement Parameter

Unit

Quantitative value

15.9

Measurement pX

7.8

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-spiroperidol

Concomitants: Compound role

RAD

Target Name

Dopamine 2 long receptor [Rattus norvegicus]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [Rattus norvegicus] Target Mutant/Chimera Details

Dopamine 2 long receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

28884191View in Reaxys

Substance Name

N%6&-(2-(4-((5-methoxy-1H-indol-3-yl)methyl)-piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine

Measurement Parameter

Unit

Quantitative value

1636

Measurement pX

5.79

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-spiroperidol

Concomitants: Compound role

RAD

368/378

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Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Reaxys ID 28884202 View in Reaxys

178/181 O

HN Br

3 F F

OH F

H 2N S

Chemical Name: N6-(2-(4-((5-bromo-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Linear Structure Formula: C25H35BrN6S*3C2HF3O2 Molecular Formula: 3C2HF3O2*C25H35BrN6S Molecular Weight: 873.635 InChI Key: PEOOBDRKXRIHJA-UHFFFAOYSA-N Note:

Substance Label (1) Label References 5b

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

129.96

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

600

Target Name

D(3) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(3) dopamine receptor; dopamine d3 receptor; drd3

Target Uniprot ID

p19020

Target, Subunit, Species D(3) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(3) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

369/378

2017-11-11 00:22:14

Substance RN

28884202View in Reaxys

Substance Name

N%6&-(2-(4-((5-bromo-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N%6&-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

Measurement Parameter

Unit

Quantitative value

12.9

Measurement pX

7.89

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-spiroperidol

Concomitants: Compound role

RAD

Target Name

Dopamine 2 long receptor [Rattus norvegicus]

Target Synonyms

dopamine 2 long receptor

Target, Subunit, Species Dopamine 2 long receptor [Rattus norvegicus] Target Mutant/Chimera Details

Dopamine 2 long receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK 293

Substance RN

28884202View in Reaxys

Substance Name

N%6&-(2-(4-((5-bromo-1H-indol-3-yl)methyl)piperazin-1-yl)ethyl)-N%6&-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

Measurement Parameter

Unit

Quantitative value

376

Measurement pX

6.42

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-spiroperidol

Concomitants: Compound role

RAD

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9179 - 9195, View in Reaxys

Reaxys ID 24253630 View in Reaxys

179/181

370/378

2017-11-11 00:22:14

Linear Structure Formula: C27H26ClN5O*(x)ClH Molecular Formula: C27H26ClN5O*(x)ClH InChI Key: XNEJSWDOGCZTKT-UHFFFAOYSA-N Note:

HN N -1 HCl

N N Cl N H

Druglikeness (1) 1 of 1

LogP

6.109

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.89

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO-K1

Cell Fraction

Membrane

Substance RN

24253630View in Reaxys

Substance Name

18a

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

6.35

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone; L 754870

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

371/378

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2 of 3

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

brain cortex

Cell Fraction

Membrane

Substance RN

24253630View in Reaxys

Substance Name

18a

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

6.23

Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 3

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

corpus striatum

372/378

2017-11-11 00:22:14

Cell Fraction

Membrane

Substance RN

24253630View in Reaxys

Substance Name

18a

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

5.57

Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Reaxys ID 24253631 View in Reaxys

180/181 Linear Structure Formula: C26H24ClN5*(x)ClH Molecular Formula: C26H24ClN5*(x)ClH InChI Key: AKCDDCBYMGUBNF-UHFFFAOYSA-N Note:

HN N

-1 HCl

Cl HN

Druglikeness (1) 1 of 1

LogP

6.194

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.66

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

373/378

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Bioassay Name

Binding

Cells/Cell Lines

CHO-K1

Cell Fraction

Membrane

Substance RN

24253631View in Reaxys

Substance Name

18b

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

6.02

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone; L 754870

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 2 of 3

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

brain cortex

Cell Fraction

Membrane

Substance RN

24253631View in Reaxys

Substance Name

18b

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

6.41

374/378

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Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 3

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

Substance RN

24253631View in Reaxys

Substance Name

18b

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

Reaxys ID 24253633 View in Reaxys

181/181

375/378

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Linear Structure Formula: C26H24ClN5O*(x)ClH Molecular Formula: C26H24ClN5O*(x)ClH InChI Key: HKHFDBLPEKODJO-UHFFFAOYSA-N Note:

HN N -1 HCl

N N Cl N H

Druglikeness (1) 1 of 1

LogP

5.788

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

66.89

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

Dopamine 4 receptor variant D4.4 [human]

Target Synonyms

dopamine 4 receptor variant d4.4

Target, Subunit, Species Dopamine 4 receptor variant D4.4 [human] Target Mutant/Chimera Details

Dopamine 4 receptor variant D4.4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Cells/Cell Lines

CHO-K1

Cell Fraction

Membrane

Substance RN

24253633View in Reaxys

Substance Name

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

6.07

Concomitants: Compound RN

632204

Concomitants: Compound name

[3H]-Spiperone; L 754870

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 2 of 3

Target Name

5-hydroxytryptamine receptor 2A [Rattus norvegicus]

376/378

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Target Synonyms

5-ht-2; 5-ht-2a; 5-hydroxytryptamine receptor 2a; htr2; htr2a; serotonin receptor 2a

Target Uniprot ID

p14842

Target PDB ID

4oaj

Target, Subunit, Species 5-hydroxytryptamine receptor 2A [Rattus norvegicus] Target Mutant/Chimera Details

5-hydroxytryptamine receptor 2A [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

brain cortex

Cell Fraction

Membrane

Substance RN

24253633View in Reaxys

Substance Name

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

6.63

Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys 3 of 3

Target Name

D(2) dopamine receptor [Rattus norvegicus]

Target Synonyms

d(2) dopamine receptor; dopamine d2 receptor; drd2

Target Uniprot ID

p61169

Target, Subunit, Species D(2) dopamine receptor [Rattus norvegicus] Target Mutant/Chimera Details

D(2) dopamine receptor [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

corpus striatum

Cell Fraction

Membrane

377/378

2017-11-11 00:22:14

Substance RN

24253633View in Reaxys

Substance Name

Substance Dose

1 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Deviation

Measurement pX

5.82

Concomitants: Compound RN

4913068; 5384418

Concomitants: Compound name

[3H]-Ketanserin; Methysergide

Concomitants: Compound role

RAD; NSB

Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576, View in Reaxys

378/378

2017-11-11 00:22:14