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Date
2 substances in Reaxys
2017-10-28 12h:47m:02s (EST)
O
1. Query
O
Search as: As drawn
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Reaxys ID 1635752 View in Reaxys
1/2 CAS Registry Number: 10035-16-2 Chemical Name: benzofuran-5-carbaldehyde; benzo[b]furan-5carboxaldehyde; 1-benzofuran-5-carbaldehyde; benzofuran-5carboxaldehyde; 5-benzofurancarboxaldehyde; 5-formylbenzofurane; 5-formylbenzofuran Linear Structure Formula: C9H6O2 Molecular Formula: C9H6O2 Molecular Weight: 146.145 Type of Substance: heterocyclic InChI Key: LLLBDLDNTMMZHL-UHFFFAOYSA-N Note:
O O
Substance Label (11) Label References 3
Yurtaeva; Tyrkov; Russian Journal of Organic Chemistry; vol. 52; nb. 2; (2016); p. 289 - 291; Zh. Org. Khim.; vol. 52; nb. 2; (2016); p. 305 - 307, View in Reaxys
III
Tyrkov; Sukhenko; Yurtaeva; Pharmaceutical Chemistry Journal; vol. 50; nb. 7; (2016); p. 436 - 439, View in Reaxys
o
Krishna, Reddy V.; Venkateswara, Rao J; Bhaskar, Reddy L.; Ram; Balram; Indian Journal of Chemistry Section B Organic and Medicinal Chemistry; vol. 54B; nb. 6; (2015); p. 791 - 797, View in Reaxys
B
Patent; DUTTA, Aloke K.; US2014/309427; (2014); (A1) English, View in Reaxys
24
Tani, Niina; Juvonen, Risto O.; Raunio, Hannu; Fashe, Muluneh; Leppänen, Jukka; Zhao, Bin; Tyndale, Rachel F.; Rahnasto-Rilla, Minna; Bioorganic and Medicinal Chemistry; vol. 22; nb. 23; (2014); p. 6655 6664, View in Reaxys
108
Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Taniguchi, Tomoya; Nomura, Takashi; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru; Phytochemistry; vol. 96; (2013); p. 132 - 147, View in Reaxys
120
Patent; PFIZER LIMITED; US2008/103130; (2008); (A1) English, View in Reaxys
10
Zajc, Barbara; Kake, Shivani; Organic Letters; vol. 8; nb. 20; (2006); p. 4457 - 4460, View in Reaxys; Ho, Jiau-Ching; Chen, Chiu-Ming; Row, Lie-Ching; Journal of Natural Products; vol. 68; nb. 12; (2005); p. 1773 - 1775, View in Reaxys
5a
Jiang, Weiqin; Guan, Jihua; Macielag, Mark J.; Zhang, Suying; Qiu, Yuhong; Kraft, Patricia; Bhattacharjee, Sheela; John, T. Matthew; Haynes-Johnson, Donna; Lundeen, Scott; Sui, Zhihua; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 2126 - 2133, View in Reaxys
12e
Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.; Tetrahedron; vol. 61; nb. 32; (2005); p. 7746 - 7755, View in Reaxys
12
Link; Sorensen; Tetrahedron Letters; vol. 41; nb. 48; (2000); p. 9213 - 9217, View in Reaxys
Patent-Specific Data (2) Location in Patent References Page/Page column
Patent; DUTTA, Aloke K.; US2014/309427; (2014); (A1) English, View in Reaxys; Patent; Kyoto University; National University Corporation Tokyo Medical and Dental University; Kinopharma, Inc.; HAGIWARA, Masatoshi; ONOGI, Hiroshi; KII, Isao; HOSOYA, Takamitsu; SUMIDA, Yuto; EP2881397; (2015); (A1) English, View in Reaxys Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2004/7491; (2004); (A1) English, View in Reaxys
Druglikeness (1) 1 of 1
LogP
1.761
H Bond Donors
0
H Bond Acceptors
1
Rotatable Bonds
1
TPSA
30.21
Lipinski Number
4
Veber Number
2
Derivative (1)
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Comment (Derivative)
References
2,4-Dinitrophenyl- Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys hydrazon Melting Point (2) 1 of 2
Melting Point [°C]
31.5 - 32
Solvent (Melting Point)
benzene; hexane
Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio; Heterocycles; vol. 38; nb. 11; (1994); p. 2463 - 2472, View in Reaxys 2 of 2
Melting Point [°C]
36 - 37
Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys Crystal Property Description (5) Colour & Other Location Properties
References
brown
Patent; DUTTA, Aloke K.; US2014/309427; (2014); (A1) English, View in Reaxys
Paragraph 0075
colourless
Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Taniguchi, Tomoya; Nomura, Takashi; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru; Phytochemistry; vol. 96; (2013); p. 132 147, View in Reaxys
yellow
Patent; Cole, Derek Cecil; Asselin, Magda; Boschelli, Diane Harris; Wissner, Allan; Wang, Yanong Daniel; Prashad, Amarnauth Shastrie; Dushin, Russell; US2007/287738; (2007); (A1) English, View in Reaxys; Patent; WYETH; WO2009/76571; (2009); (A1) English, View in Reaxys
orange
Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Iwashita, Hiroki; Uno, Yumiko; Onishi, Tomohiro; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret P.; Snell, Gyorgy P.; Takizawa, Masayuki; Itoh, Fumio; Kori, Masakuni; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6270 - 6286, View in Reaxys
light-yellow
Patent; SCHERING CORPORATION; PHARMACOPEIA, INC.; WO2004/11418; (2004); (A1) English, View in Reaxys; Patent; PHARMACOPEIA, INC.; WO2004/33440; (2004); (A1) English, View in Reaxys
NMR Spectroscopy (9) 1 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Original Text (NMR Spectroscopy)
1H
NMR (500 MHz, CDCl3): δ 10.07 (s, 1H), 8.15 (d, J=1.2 Hz, 1H), 7.87 (dd, J=1.5, 8.6 Hz, 1H), 7.73 (d, J=2.4 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H), 6.90 (m, 1H)
Location
Paragraph 0076
Signals [ppm]
10.07; 8.15; 7.87; 7.73; 7.62; 6.9
Kind of signal
s, 1H; d, J=1.2 Hz, 1H; dd, J=1.5, 8.6 Hz, 1H; d, J=2.4 Hz, 1H; d, J=8.5 Hz, 1H; m, 1H
Patent; DUTTA, Aloke K.; US2014/309427; (2014); (A1) English, View in Reaxys 2 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
125
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Original Text (NMR Spectroscopy)
13C
Location
Paragraph 0077
Signals [ppm]
191.7; 158.2; 146.7; 132.2; 125.7; 124.6; 112.1; 107.2
NMR (125 MHz, CDCl3): δ 191.7, 158.2, 146.7, 132.2, 125.7, 124.6, 112.1, 107.2
Patent; DUTTA, Aloke K.; US2014/309427; (2014); (A1) English, View in Reaxys 3 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Taniguchi, Tomoya; Nomura, Takashi; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru; Phytochemistry; vol. 96; (2013); p. 132 - 147, View in Reaxys 4 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.; Tetrahedron; vol. 61; nb. 32; (2005); p. 7746 - 7755, View in Reaxys 5 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.; Tetrahedron; vol. 61; nb. 32; (2005); p. 7746 - 7755, View in Reaxys 6 of 9
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.; Tetrahedron; vol. 61; nb. 32; (2005); p. 7746 - 7755, View in Reaxys 7 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy)
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Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio; Heterocycles; vol. 38; nb. 11; (1994); p. 2463 - 2472, View in Reaxys 8 of 9
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)
1H-1H
Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio; Heterocycles; vol. 38; nb. 11; (1994); p. 2463 - 2472, View in Reaxys 9 of 9
Description (NMR Spec- NMR troscopy) Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys
IR Spectroscopy (3) 1 of 3
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
CHCl3
Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.; Tetrahedron; vol. 61; nb. 32; (2005); p. 7746 - 7755, View in Reaxys 2 of 3
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Comment (IR Spectroscopy)
1702 cm**(-1)
Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio; Heterocycles; vol. 38; nb. 11; (1994); p. 2463 - 2472, View in Reaxys 3 of 3
Description (IR Spectroscopy)
IR
Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys Mass Spectrometry (3) Description (Mass Comment (Mass Spectrometry) Spectrometry) spectrum
References Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.; Tetrahedron; vol. 61; nb. 32; (2005); p. 7746 - 7755, View in Reaxys
LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)
Molecular peak
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2004/7491; (2004); (A1) English, View in Reaxys
Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
UV/VIS
Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys Isolation from Natural Product (2) Isolation from References Natural Product fresh flowers of Ho, Jiau-Ching; Chen, Chiu-Ming; Row, Lie-Ching; Journal of Natural Products; vol. 68; nb. 12; (2005); p. Tetrapanax papy- 1773 - 1775, View in Reaxys riferus (Hook) K. Koch (Araliaceae)
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collected from Miaoli County, Taiwan aus Stereum sub- Bu'Lock,J.D. et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 1037 - 1046, View in Reaxys pileatum Medchem (5) 1 of 5
Target Mutant/Chimera Details
Cytochrome P450 2A6 [human]:Wild
Substance Action on Target
Inhibitor
Target Species (Bioactivity)
human
Target Subunit Proteins
Cytochrome P450 2A6 [human]
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
In vitro inhibitory concentration of compound against human CYTOCHROME P450 2A6 expressed in baculovirus infected insect cells upon incubation for 10 mins at 37 degree C in presence of 0.33 mM NADPH
Substance RN
1635752View in Reaxys
Measurement Parameter
IC50
Unit
µM
Qualitative value
=
Quantitative value
0.4
Measurement pX
6.4
Target, Subunit, Species Cytochrome P450 2A6 [human] Tani, Niina; Juvonen, Risto O.; Raunio, Hannu; Fashe, Muluneh; Leppänen, Jukka; Zhao, Bin; Tyndale, Rachel F.; Rahnasto-Rilla, Minna; Bioorganic and Medicinal Chemistry; vol. 22; nb. 23; (2014); p. 6655 - 6664, View in Reaxys
2 of 5
Target Subunit Synonyms
1,4-cineole 2-exo-monooxygenase (cytochrome p450 2a6); coumarin 7-hydroxylase; cyp2a3; cyp2a6; cypiia6; cytochrome p450 2a6; cytochrome p450 iia3; cytochrome p450(i)
Target Uniprot ID
p11509
Target PDB ID
1z10; 1z11; 2fdu; 2fdv; 2fdw; 2fdy; 3ebs; 3t3q; 3t3r; 4ejj; 4rui
Target Mutant/Chimera Details
Cytochrome P450 2A6:Wild
Substance Action on Target
Inhibitor
Target Subunit Proteins
Cytochrome P450 2A6
Substance Effect
inhibitory activity
Bioassay Category
Metabolism/Transport
Bioassay Details
In vitro inhibition constant of compound against nicotine (30 uM and 300 uM) oxidation by CYTOCHROME P450 2A6 in supersomes in presence of 1 mM NADPH upon incubation in 50 mM Tris-HCl, pH 7.4 for 15 mins at 37 degree C
Cells/Cell Lines
supersomes
Substance RN
1635752View in Reaxys
Qualitative Results
Competitive inhibition
Measurement Parameter
Ki
Unit
µM
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Qualitative value
=
Quantitative value
5.5
Measurement pX
5.26
Target, Subunit, Species Cytochrome P450 2A6 Tani, Niina; Juvonen, Risto O.; Raunio, Hannu; Fashe, Muluneh; Leppänen, Jukka; Zhao, Bin; Tyndale, Rachel F.; Rahnasto-Rilla, Minna; Bioorganic and Medicinal Chemistry; vol. 22; nb. 23; (2014); p. 6655 - 6664, View in Reaxys
3 of 5
Target Subunit Synonyms
cytochrome p450 2a6
Measurement Object
NICOTINE OXIDATION
Target Mutant/Chimera Details
Cytochrome P450 2A6 [human]:Wild
Substance Action on Target
Inhibitor
Target Species (Bioactivity)
human
Target Subunit Proteins
Cytochrome P450 2A6 [human]
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
In vitro inhibition constant of compound against human CYTOCHROME P450 2A6 expressed in baculovirus infected insect cells upon incubation for 10 mins at 37 degree C in presence of 0.33 mM NADPH
Substance RN
1635752View in Reaxys
Qualitative Results
Competitive inhibition
Measurement Parameter
Qualitative
Unit
µM
Qualitative value
=
Quantitative value
0.07
Target, Subunit, Species Cytochrome P450 2A6 [human] Tani, Niina; Juvonen, Risto O.; Raunio, Hannu; Fashe, Muluneh; Leppänen, Jukka; Zhao, Bin; Tyndale, Rachel F.; Rahnasto-Rilla, Minna; Bioorganic and Medicinal Chemistry; vol. 22; nb. 23; (2014); p. 6655 - 6664, View in Reaxys
4 of 5
Target Subunit Synonyms
1,4-cineole 2-exo-monooxygenase (cytochrome p450 2a6); coumarin 7-hydroxylase; cyp2a3; cyp2a6; cypiia6; cytochrome p450 2a6; cytochrome p450 iia3; cytochrome p450(i)
Target Uniprot ID
p11509
Target PDB ID
1z10; 1z11; 2fdu; 2fdv; 2fdw; 2fdy; 3ebs; 3t3q; 3t3r; 4ejj; 4rui
Target Mutant/Chimera Details
Cytochrome P450 2A6:Wild
Substance Action on Target
Inhibitor
Target Subunit Proteins
Cytochrome P450 2A6
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Half maximal inactivation rate constant of compound against CYTOCHROME P450 2A6 using 10 uM coumarin as substrate upon incubation in 50 mM Tris-HCl, pH 7.4 for 10 mins at 37 degree C in presence of 0.33 mM NADPH
Substance RN
1635752View in Reaxys
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Qualitative Results
Range = 2.4 uM to 22 uM
Measurement Parameter
Ki
Unit
µM
Quantitative value
2.4 - 22
Measurement pX
5.62
Target, Subunit, Species Cytochrome P450 2A6 Tani, Niina; Juvonen, Risto O.; Raunio, Hannu; Fashe, Muluneh; Leppänen, Jukka; Zhao, Bin; Tyndale, Rachel F.; Rahnasto-Rilla, Minna; Bioorganic and Medicinal Chemistry; vol. 22; nb. 23; (2014); p. 6655 - 6664, View in Reaxys
5 of 5
Target Subunit Synonyms
cytochrome p450 2a6
Target Mutant/Chimera Details
Cytochrome P450 2A6:Wild
Substance Action on Target
Inhibitor
Target Subunit Proteins
Cytochrome P450 2A6
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Maximum inactivation rate constant of compound against CYTOCHROME P450 2A6 using 10 uM coumarin as substrate upon incubation in 50 mM Tris-HCl, pH 7.4 for 10 mins at 37 degree C in presence of 0.33 mM NADPH
Substance RN
1635752View in Reaxys
Qualitative Results
Range = 0.08 min-1 to 0.22 min-1
Measurement Parameter
kinact
Unit
min-1
Qualitative value
R
Quantitative value
0.08
Target, Subunit, Species Cytochrome P450 2A6 Tani, Niina; Juvonen, Risto O.; Raunio, Hannu; Fashe, Muluneh; Leppänen, Jukka; Zhao, Bin; Tyndale, Rachel F.; Rahnasto-Rilla, Minna; Bioorganic and Medicinal Chemistry; vol. 22; nb. 23; (2014); p. 6655 - 6664, View in Reaxys Target Subunit Synonyms
cytochrome p450 2a6
Reaxys ID 9995520 View in Reaxys
2/2 (13)CH
Linear Structure Formula: C8 6O2 Molecular Formula: C9H6O2 Molecular Weight: 147.134 Type of Substance: heterocyclic InChI Key: LLLBDLDNTMMZHL-PTQBSOBMSA-N Note:
O O 13 C H
Druglikeness (1) 1 of 1
LogP
1.761
H Bond Donors
0
H Bond Acceptors
1
Rotatable Bonds
1
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TPSA
30.21
Lipinski Number
4
Veber Number
2
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