1,2,3-Trimethoxy-5-(2-nitrovinyl)benzene [C11H13NO5]

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2017-11-16 00h:20m:58s (EST)

NO 2

O O

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Reaxys ID 2139334 View in Reaxys

1/3 CAS Registry Number: 40663-31-8 Chemical Name: 1-(3,4,5-trimethoxyphenyl)-2-nitroethene; (E)-1,2,3-trimethoxy-5-(2-nitrovinyl)benzene; (E)-1-nitro-2(3,4,5-trimethoxyphenyl)ethene; 3,4,5-trimethoxy-trans-β-nitrostyrene; trans-3,4,5-trimethoxy-β-nitrostyrene; 3,4,5-trimethoxyβ-nitrostyrene; 3,4,5-trimethoxy-β-nitrostyrene Linear Structure Formula: C11H13NO5 Molecular Formula: C11H13NO5 Molecular Weight: 239.228 Type of Substance: isocyclic InChI Key: PEPYBEJQAIGLRE-SNAWJCMRSA-N Note:

O O

E O

O N O

Substance Label (31) Label References 2e

González-Olvera; Vergara-Arenas; Negrón-Silva; Angeles-Beltrán; Lomas-Romero; Gutiérrez-Carrillo; Lara; Morales-Serna; RSC Advances; vol. 5; nb. 120; (2015); p. 99188 - 99192, View in Reaxys; Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165, View in Reaxys; Vergara-Arenas, Blanca Ivonne; Lomas-Romero, Leticia; Ángeles-Beltrán, Deyanira; Negrón-Silva, Guillermo Enrique; Gutiérrez-Carrillo, Atilano; Lara, Víctor Hugo; Morales-Serna, José Antonio; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2690 - 2694, View in Reaxys

2

Feng, Cheng-Tao; Zhu, Hui-Zhi; Li, Zhong; Luo, Zaigang; Wu, Song-Song; Ma, Shi-Tang; Tetrahedron Letters; vol. 57; nb. 7; (2016); p. 800 - 803, View in Reaxys; Mahato, Karuna; Bagdi, Prasanta Ray; Khan, Abu T.; Organic and Biomolecular Chemistry; vol. 15; nb. 26; (2017); p. 5625 - 5634, View in Reaxys

4r

Akondi, Adinarayana Murthy; Mekala, Sowmya; Kantam, Mannepalli Lakshmi; Trivedi, Rajiv; Raju Chowhan; Das, Amitava; New Journal of Chemistry; vol. 41; nb. 2; (2017); p. 873 - 878, View in Reaxys

2f

Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys

1s

Guo, Shuhui; Mi, Xueling; Tetrahedron Letters; vol. 58; nb. 30; (2017); p. 2881 - 2884, View in Reaxys

3c

Enders, Dieter; Tedeschi, Livio; Bats, Jan Willem; Angewandte Chemie - International Edition; vol. 39; nb. 24; (2000); p. 4605 - 4607, View in Reaxys; Luo, Zai-Gang; Xu, Feng; Fang, Yu-Yu; Liu, Peng; Xu, XueMei; Feng, Cheng-Tao; Li, Zhong; He, Jie; Research on Chemical Intermediates; vol. 42; nb. 6; (2016); p. 6079 - 6087, View in Reaxys

1

Guo, Sheng-Rong; Yuan, Yan-Qin; Synlett; vol. 26; nb. 14; (2015); p. 1961 - 1968; Art.No: ST-2015W0187-L, View in Reaxys

8c

Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys

6f

Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 3018, View in Reaxys

2c

Enders, Dieter; Tedeschi, Livio; Foerster, Dominik; Synthesis; nb. 9; (2006); p. 1447 - 1460, View in Reaxys; Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288, View in Reaxys

4d

Enders, Dieter; Hahn, Robert; Atodiresei, Iuliana; Advanced Synthesis and Catalysis; vol. 355; nb. 6; (2013); p. 1126 - 1136, View in Reaxys

3e

Jalal, Swapnadeep; Sarkar, Soumen; Bera, Krishnendu; Maiti, Sukhendu; Jana, Umasish; European Journal of Organic Chemistry; nb. 22; (2013); p. 4823 - 4828, View in Reaxys

4

Abdukader, Ablimit; Xue, Qicai; Lin, Aijun; Zhang, Ming; Cheng, Yixiang; Zhu, Chengjian; Tetrahedron Letters; vol. 54; nb. 44; (2013); p. 5898 - 5900, View in Reaxys

11a

Puerto Galvis, Carlos E.; Kouznetsov, Vladimir V.; Organic and Biomolecular Chemistry; vol. 11; nb. 42; (2013); p. 7372 - 7386, View in Reaxys

5c

Suzuki, Tomiko M.; Yamamoto, Masami; Fukumoto, Keiko; Akimoto, Yusuke; Yano, Kazuhisa; Journal of Catalysis; vol. 251; nb. 2; (2007); p. 249 - 257, View in Reaxys

3, Tab. 1, entry 6

Nyerges, Miklos; Somfai, Barbara; Toth, Judit; Toke, Laszlo; Dancso, Andras; Blasko, Gabor; Synthesis; nb. 12; (2005); p. 2039 - 2045; Art.No: P00405SS, View in Reaxys

Table 1. Product 10.

Sridhar Rao; Srinivas; Suresh Babu; Madhusudana Rao; Tetrahedron Letters; vol. 46; nb. 47; (2005); p. 8141 - 8143, View in Reaxys

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23 for 21h,i

Taylor, Edward C.; Liu, Bin; Journal of Organic Chemistry; vol. 68; nb. 26; (2003); p. 9938 - 9947, View in Reaxys

TriMeO-NS

Kaap, Sylvia; Quentin, Iris; Tamiru, Dereje; Shaheen, Mohammed; Eger, Kurt; Steinfelder, Hans Juergen; Biochemical Pharmacology; vol. 65; nb. 4; (2003); p. 603 - 610, View in Reaxys

8

Das, Jaya Prakash; Sinha, Pradipta; Roy, Sujit; Organic Letters; vol. 4; nb. 18; (2002); p. 3055 - 3058, View in Reaxys

3g

Liu, Ju-Tsung; Yao, Ching-Fa; Tetrahedron Letters; vol. 42; nb. 35; (2001); p. 6147 - 6150, View in Reaxys

2d

Fierro; Rezende; Sepulveda-Boza; Reyes-Parada; Cassels; Journal of Chemical Research - Part S; nb. 7; (2001); p. 294 - 296, View in Reaxys

2h

Enders, Dieter; Teschner, Pascal; Raabe, Gerhard; Runsink, Jan; European Journal of Organic Chemistry; nb. 23; (2001); p. 4463 - 4477, View in Reaxys

1j

Node, Manabu; Nishide, Kiyoharu; Imazato, Hitoshi; Kurosaki, Ryuichi; Inoue, Takehisa; Ikariya, Takao; Chemical Communications; nb. 22; (1996); p. 2559 - 2560, View in Reaxys

table 1, entry 6

Nyerges, Miklos; Balazs, Laszlo; Kadas, Istvan; Bitter, Istvan; Koevesdi, Istvan; Toeke, Laszlo; Tetrahedron; vol. 51; nb. 24; (1995); p. 6783 - 6788, View in Reaxys

1i

Torres; Cassels; Rezende; Synthetic Communications; vol. 25; nb. 8; (1995); p. 1239 - 1247, View in Reaxys

5f

Hassner; Rai; Dehaen; Synthetic Communications; vol. 24; nb. 12; (1994); p. 1669 - 1682, View in Reaxys

1d

Rama, Rajagopal; Srinivasan, Vankipuram R.; Heterocycles; vol. 32; nb. 1; (1991); p. 33 - 39, View in Reaxys

Table I entry 9

Sinhababu, Achintya K.; Borchardt, Ronald T.; Tetrahedron Letters; vol. 24; nb. 3; (1983); p. 227 - 230, View in Reaxys

1o

Seebach,D. et al.; Chemische Berichte; vol. 108; (1975); p. 1924 - 1945, View in Reaxys

76

Dore,J.-C. et al.; Chimica Therapeutica; vol. 6; (1971); p. 167 - 185, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.974

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

5

TPSA

73.51

Lipinski Number

4

Veber Number

2

Related Structure (1) Related Structure References Bezueglich der Konfiguration vgl. die Angaben im Artikel #trans!-βNitro-4-methoxystyrol (S. 2388).

Beilstein Handbook, View in Reaxys

Melting Point (9) 1 of 9

Melting Point [°C]

114 - 116

Location

supporting information

Vergara-Arenas, Blanca Ivonne; Lomas-Romero, Leticia; Ángeles-Beltrán, Deyanira; Negrón-Silva, Guillermo Enrique; Gutiérrez-Carrillo, Atilano; Lara, Víctor Hugo; Morales-Serna, José Antonio; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2690 - 2694, View in Reaxys 2 of 9

Melting Point [°C]

122 - 124

Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165, View in Reaxys 3 of 9

Melting Point [°C]

120 - 122

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Luo, Zai-Gang; Xu, Feng; Fang, Yu-Yu; Liu, Peng; Xu, Xue-Mei; Feng, Cheng-Tao; Li, Zhong; He, Jie; Research on Chemical Intermediates; vol. 42; nb. 6; (2016); p. 6079 - 6087, View in Reaxys 4 of 9

Melting Point [°C]

115 - 116

Location

supporting information

Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys 5 of 9

Melting Point [°C]

120

Location

supporting information

Jalal, Swapnadeep; Sarkar, Soumen; Bera, Krishnendu; Maiti, Sukhendu; Jana, Umasish; European Journal of Organic Chemistry; nb. 22; (2013); p. 4823 - 4828, View in Reaxys; Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 - 3018, View in Reaxys 6 of 9

Melting Point [°C]

121

Solvent (Melting Point)

chloroform

Location

supporting information

Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288, View in Reaxys 7 of 9

Melting Point [°C]

120 - 121

Seebach,D. et al.; Chemische Berichte; vol. 108; (1975); p. 1924 - 1945, View in Reaxys; Slotta; Szyszka; Journal fuer Praktische Chemie (Leipzig); vol. <2> 137; (1933); p. 339,349, View in Reaxys 8 of 9

Melting Point [°C]

120

Solvent (Melting Point)

methanol

Dore,J.-C. et al.; Chimica Therapeutica; vol. 6; (1971); p. 167 - 185, View in Reaxys 9 of 9

Melting Point [°C]

122 - 123

Solvent (Melting Point)

ethanol

Trager; Huitric; Journal of pharmaceutical sciences; vol. 54; nb. 10; (1965); p. 1552 - 1553, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties yellow

supporting information

yellow

References Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288, View in Reaxys; Jalal, Swapnadeep; Sarkar, Soumen; Bera, Krishnendu; Maiti, Sukhendu; Jana, Umasish; European Journal of Organic Chemistry; nb. 22; (2013); p. 4823 - 4828, View in Reaxys; Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys; VergaraArenas, Blanca Ivonne; Lomas-Romero, Leticia; Ángeles-Beltrán, Deyanira; Negrón-Silva, Guillermo Enrique; Gutiérrez-Carrillo, Atilano; Lara, Víctor Hugo; Morales-Serna, José Antonio; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2690 - 2694, View in Reaxys Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165, View in Reaxys; Luo, Zai-Gang; Xu, Feng; Fang, Yu-Yu; Liu, Peng; Xu, Xue-Mei; Feng, Cheng-Tao; Li, Zhong; He, Jie; Research on Chemical Intermediates; vol. 42; nb. 6; (2016); p. 6079 - 6087, View in Reaxys

NMR Spectroscopy (17) 1 of 17

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

1H

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

400

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Location

supporting information

Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288, View in Reaxys; Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165, View in Reaxys; Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L, View in Reaxys 2 of 17

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

Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 1082; Art.No: ST-2016-W0789-L, View in Reaxys 3 of 17

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

1H

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

400

Location

supporting information

Vergara-Arenas, Blanca Ivonne; Lomas-Romero, Leticia; Ángeles-Beltrán, Deyanira; Negrón-Silva, Guillermo Enrique; Gutiérrez-Carrillo, Atilano; Lara, Víctor Hugo; Morales-Serna, José Antonio; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2690 - 2694, View in Reaxys 4 of 17

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

13C

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

100.6

Location

supporting information

Vergara-Arenas, Blanca Ivonne; Lomas-Romero, Leticia; Ángeles-Beltrán, Deyanira; Negrón-Silva, Guillermo Enrique; Gutiérrez-Carrillo, Atilano; Lara, Víctor Hugo; Morales-Serna, José Antonio; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2690 - 2694, View in Reaxys 5 of 17

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

13C

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

100

Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165, View in Reaxys 6 of 17

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

1H

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

500

Luo, Zai-Gang; Xu, Feng; Fang, Yu-Yu; Liu, Peng; Xu, Xue-Mei; Feng, Cheng-Tao; Li, Zhong; He, Jie; Research on Chemical Intermediates; vol. 42; nb. 6; (2016); p. 6079 - 6087, View in Reaxys 7 of 17

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

13C

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

125

Luo, Zai-Gang; Xu, Feng; Fang, Yu-Yu; Liu, Peng; Xu, Xue-Mei; Feng, Cheng-Tao; Li, Zhong; He, Jie; Research on Chemical Intermediates; vol. 42; nb. 6; (2016); p. 6079 - 6087, View in Reaxys 8 of 17

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

1H

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

21.84

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys 9 of 17

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

13C

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

125

Location

supporting information

Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys 10 of 17

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

1H

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

400

Location

supporting information

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Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 - 3018, View in Reaxys 11 of 17

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

13C

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

100

Location

supporting information

Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 - 3018, View in Reaxys 12 of 17

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

13C

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

101

Location

supporting information

Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288, View in Reaxys 13 of 17

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

1H

Coupling Nuclei

1H

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

300

Location

supporting information

Jalal, Swapnadeep; Sarkar, Soumen; Bera, Krishnendu; Maiti, Sukhendu; Jana, Umasish; European Journal of Organic Chemistry; nb. 22; (2013); p. 4823 - 4828, View in Reaxys 14 of 17

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

13C

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

75

Location

supporting information

Jalal, Swapnadeep; Sarkar, Soumen; Bera, Krishnendu; Maiti, Sukhendu; Jana, Umasish; European Journal of Organic Chemistry; nb. 22; (2013); p. 4823 - 4828, View in Reaxys 15 of 17

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

1H

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Solvents (NMR Spectro- CDCl3 scopy) Das, Jaya Prakash; Sinha, Pradipta; Roy, Sujit; Organic Letters; vol. 4; nb. 18; (2002); p. 3055 - 3058, View in Reaxys 16 of 17

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- CDCl3 scopy) Das, Jaya Prakash; Sinha, Pradipta; Roy, Sujit; Organic Letters; vol. 4; nb. 18; (2002); p. 3055 - 3058, View in Reaxys 17 of 17

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Das, Jaya Prakash; Sinha, Pradipta; Roy, Sujit; Organic Letters; vol. 4; nb. 18; (2002); p. 3055 - 3058, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Location

supporting information

Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Location

supporting information

Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 - 3018, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165, View in Reaxys

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); spectrum

Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288, View in Reaxys; Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP, View in Reaxys

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 - 3018, View in Reaxys

Medchem (36) 1 of 36

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

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Bioassay Details

Target : rat pituitary GH3 tumor cellsBioassay : cells treated with title comp. for 24 h; fixed; methylene blue added for 30 min, pH 8.5; absorption measured at 650 nm in microplate reader

Substance RN

2139334View in Reaxys

Substance Name

1458445

Substance Dose

10 µM

Measurement Parameter

LC50

Unit

µM

Quantitative value

10

Measurement pX

5

Kaap, Sylvia; Quentin, Iris; Tamiru, Dereje; Shaheen, Mohammed; Eger, Kurt; Steinfelder, Hans Juergen; Biochemical Pharmacology; vol. 65; nb. 4; (2003); p. 603 - 610, View in Reaxys 2 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum fungicidal concentration of the compound dissolved in DMSO against Neisseria gonorrhoeae ATCC 49226 upon incubation for 24 h at 37 degree C by broth microdilution assay

Biological Species/NCBI Neisseria gonorrhoeae ATCC 49226 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MFC

Unit

µg/mL

Measurement Object

Minimum fungicidal concentration

Qualitative value

=

Quantitative value

8

Measurement pX

4.48

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 3 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Cryptococcus neoformans ATCC 90112 by disk diffusion susceptibility assay; MIC = 3.12 - 6.25 ug/ disk

Biological Species/NCBI Cryptococcus neoformans ATCC 90112 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 3.12 - 6.25 ug/disk

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

6.25

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 4 of 36

Bioassay Category

In Vitro (Efficacy)

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9/24

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Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Stenotrophomonas maltophilia ATCC 13637 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Stenotrophomonas maltophilia ATCC 13637 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 5 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Stenotrophomonas maltophilia ATCC 13637 by disk diffusion susceptibility assay

Biological Species/NCBI Stenotrophomonas maltophilia ATCC 13637 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

100

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 6 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Escherichia coli ATCC 25922 by disk diffusion susceptibility assay

Biological Species/NCBI Escherichia coli ATCC 25922 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

100

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 7 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Enterococcus faecalis ATCC 29212 by disk diffusion susceptibility assay; MIC = 50 - 100 ug/disk

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/24

2017-11-16 00:28:22


Biological Species/NCBI Enterococcus faecalis ATCC 29212 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 50 - 100 ug/disk

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

100

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 8 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Streptococcus pneumoniae ATCC 6303 by disk diffusion susceptibility assay; MIC = 3.12 - 6.25 ug/disk

Biological Species/NCBI Streptococcus pneumoniae ATCC 6303 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 3.12 - 6.25 ug/disk

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

6.25

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 9 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human ovary cancer OVCAR-3 cells

Biological Species/NCBI Human ID Cells/Cell Lines

NIH:OVCAR-3

Substance RN

2139334View in Reaxys

Measurement Parameter

GI50

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

=

Quantitative value

0.42

Measurement pX

5.75

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 10 of 36

Bioassay Category

In Vitro (Efficacy)

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11/24

2017-11-16 00:28:22


Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Escherichia coli ATCC 25922 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Escherichia coli ATCC 25922 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 11 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum fungicidal concentration of the compound dissolved in DMSO against Cryptococcus neoformans ATCC 90112 upon incubation for 48 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Cryptococcus neoformans ATCC 90112 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MFC

Unit

µg/mL

Measurement Object

Minimum fungicidal concentration

Qualitative value

=

Quantitative value

16

Measurement pX

4.17

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 12 of 36

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human prostate cancer DU-145 cells

Biological Species/NCBI Human ID Cells/Cell Lines

DU 145

Substance RN

2139334View in Reaxys

Measurement Parameter

GI50

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

=

Quantitative value

1

Measurement pX

5.38

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

12/24

2017-11-16 00:28:22


Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 13 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Enterobacter cloacae ATCC 13047 by disk diffusion susceptibility assay

Biological Species/NCBI Enterobacter cloacae ATCC 13047 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

100

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 14 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Cryptococcus neoformans ATCC 90112 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Cryptococcus neoformans ATCC 90112 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

16

Measurement pX

4.17

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 15 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human breast cancer MCF-7 cells; NA = Not available

Biological Species/NCBI Human ID Cells/Cell Lines

MCF-7

Substance RN

2139334View in Reaxys

Qualitative Results

NA = Not available

Measurement Parameter

GI50

Measurement Object

Growth inhibition

Qualitative value

ND

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

13/24

2017-11-16 00:28:22


16 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Staphylococcus aureus ATCC 29213 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Staphylococcus aureus ATCC 29213 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 17 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human melanoma cancer SK-MEL-5 cells

Biological Species/NCBI Human ID Cells/Cell Lines

SK-MEL V

Substance RN

2139334View in Reaxys

Qualitative Results

NA = Not available

Measurement Parameter

GI50

Measurement Object

Growth inhibition

Qualitative value

ND

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 18 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Enterobacter cloacae ATCC 13047 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Enterobacter cloacae ATCC 13047 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 19 of 36

Bioassay Category

In Vitro (Efficacy)

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14/24

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Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Micrococcus luteus presque isle 456 by disk diffusion susceptibility assay; MIC = 25 - 50 ug/disk

Biological Species/NCBI Micrococcus luteus PRESQUE ISLE 456 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 25 - 50 ug/disk

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

50

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 20 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Effective dose of the compound against murine leukemia P388 cells

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

P388 cell line

Substance RN

2139334View in Reaxys

Measurement Parameter

EC50

Unit

µg/mL

Measurement Object

Effective dose

Qualitative value

=

Quantitative value

1.1

Measurement pX

5.34

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 21 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human CNS cancer SF268 cells; NA = Not available

Biological Species/NCBI Human ID Cells/Cell Lines

SF268

Substance RN

2139334View in Reaxys

Qualitative Results

NA = Not available

Measurement Parameter

GI50

Measurement Object

Growth inhibition

Qualitative value

ND

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 22 of 36

Bioassay Category

In Vitro (Efficacy)

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15/24

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Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Candida albicans ATCC 90028 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

32

Measurement pX

3.87

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 23 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Neisseria gonorrhoeae ATCC 49226 by disk diffusion susceptibility assay; MIC = 0.78 - 1.56 ug/disk

Biological Species/NCBI Neisseria gonorrhoeae ATCC 49226 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 0.78 - 1.56 ug/disk

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

1.56

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 24 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human colon cancer KM20L2 cells

Biological Species/NCBI Human ID Cells/Cell Lines

KM-20L2

Substance RN

2139334View in Reaxys

Measurement Parameter

GI50

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

=

Quantitative value

1.3

Measurement pX

5.27

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys

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16/24

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25 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum fungicidal concentration of the compound dissolved in DMSO against Candida albicans ATCC 90028 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MFC

Unit

µg/mL

Measurement Object

Minimum fungicidal concentration

Qualitative value

=

Quantitative value

32

Measurement pX

3.87

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 26 of 36

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human renal cancer A498 cells

Biological Species/NCBI Human ID Cells/Cell Lines

A-498

Substance RN

2139334View in Reaxys

Qualitative Results

NA = Not available

Measurement Parameter

GI50

Measurement Object

Growth inhibition

Qualitative value

ND

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 27 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human lung-NSC cancer NCI-H460 cells

Biological Species/NCBI Human ID Cells/Cell Lines

NCI-H460

Substance RN

2139334View in Reaxys

Measurement Parameter

GI50

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

=

Quantitative value

1.1

Measurement pX

5.34

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17/24

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Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 28 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Streptococcus pneumoniae ATCC 6303 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Streptococcus pneumoniae ATCC 6303 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 29 of 36

Target Name

Tubulin

Target Synonyms

tubulin

Target, Subunit, Species Tubulin Target Mutant/Chimera Details

Tubulin:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against tubulin polymerization

Substance RN

2139334View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

=

Quantitative value

4.5

Deviation

0.2

Measurement pX

5.35

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 30 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Staphylococcus aureus ATCC 29213 by disk diffusion susceptibility assay; MIC = 12.5 - 25 ug/disk

Biological Species/NCBI Staphylococcus aureus ATCC 29213 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 12.5 - 25 ug/disk

Measurement Parameter

MIC

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18/24

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Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

25

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 31 of 36

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human pancreatic cancer BXPC-3 cells

Biological Species/NCBI Human ID Cells/Cell Lines

BXPC-3

Substance RN

2139334View in Reaxys

Measurement Parameter

GI50

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

=

Quantitative value

1.4

Measurement pX

5.23

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 32 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Neisseria gonorrhoeae ATCC 49226 upon incubation for 24 h at 37 degree C by broth microdilution assay

Biological Species/NCBI Neisseria gonorrhoeae ATCC 49226 ID Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

4

Measurement pX

4.78

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 33 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Micrococcus luteus presque isle 456 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Micrococcus luteus PRESQUE ISLE 456 ID Substance RN

2139334View in Reaxys

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19/24

2017-11-16 00:28:22


Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 34 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Growth inhibition of the compound against human CNS cancer SF295 cells

Biological Species/NCBI Human ID Cells/Cell Lines

SF-295

Substance RN

2139334View in Reaxys

Measurement Parameter

GI50

Unit

µg/mL

Measurement Object

Growth inhibition

Qualitative value

=

Quantitative value

1.3

Measurement pX

5.27

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 35 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Candida albicans ATCC 90028 by disk diffusion susceptibility assay; MIC = 3.12 - 6.25 ug/disk

Biological Species/NCBI Candida albicans ATCC 90028 ID Substance RN

2139334View in Reaxys

Qualitative Results

MIC = 3.12 - 6.25 ug/disk

Measurement Parameter

MIC

Unit

µg

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

=

Quantitative value

6.25

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys 36 of 36

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration of the compound dissolved in DMSO against Enterococcus faecalis ATCC 29212 upon incubation for 24 h at 35 degree C by broth microdilution assay

Biological Species/NCBI Enterococcus faecalis ATCC 29212 ID

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2017-11-16 00:28:22


Substance RN

2139334View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Measurement Object

Minimum Inhibitory Concentration

Qualitative value

>

Quantitative value

64

Measurement pX

1

Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612, View in Reaxys

Reaxys ID 2623048 View in Reaxys

2/3 CAS Registry Number: 6316-70-7 Chemical Name: 3,4,5-trimethoxy-β-nitrostyrene; 1,2,3-trimethoxy-5-(2-nitroethenyl)benzene; 1,2,3-trimethoxy-5-(2-nitrovinyl)benzene; 2-(3,4,5-trimethoxyphenyl)-1-nitroethene; β-nitro-3,4,5-trimethoxystyrene; 3,4,5-trimethyl-β-nitrostyrene; 3,4,5-trimethoxy-β-nitro-styrene Linear Structure Formula: C11H13NO5 Molecular Formula: C11H13NO5 Molecular Weight: 239.228 Type of Substance: isocyclic InChI Key: PEPYBEJQAIGLRE-UHFFFAOYSA-N Note:

O O

O N O

O

Substance Label (23) Label References 1

Li, Guangxun; Wu, Lei; Lv, Gang; Liu, Hongxin; Fu, Qingquan; Zhang, Xiaomei; Tang, Zhuo; Chemical Communications; vol. 50; nb. 47; (2014); p. 6246 - 6248, View in Reaxys; Sharma, Pankaj; Kumar, A. Niggula P.; Senwar, Kishna R.; Forero-Doria, Oscar; Nachtigall, Fabiane M.; Santos, Leonardo S.; Shankaraiah; Journal of the Brazilian Chemical Society; vol. 28; nb. 4; (2017); p. 589 - 597, View in Reaxys

2h

Quintard, Adrien; Rodriguez, Jean; Organic Letters; vol. 19; nb. 3; (2017); p. 722 - 725, View in Reaxys

5a

Sridhar, Gattu; Somnath, Mudavath; Sharma, Gangavaram V. M.; Prashanth, Thodupunuri; Synthetic Communications; vol. 47; nb. 6; (2017); p. 551 - 556, View in Reaxys

3l

Wang, Xiao; Wu, Lin; Yang, Peng; Song, Xiang-Jia; Ren, Hong-Xia; Peng, Lin; Wang, Li-Xin; Organic Letters; vol. 19; nb. 12; (2017); p. 3051 - 3054, View in Reaxys

4j

Rombola, Michael; Sumaria, Chintan S.; Montgomery, Thomas D.; Rawal, Viresh H.; Journal of the American Chemical Society; vol. 139; nb. 15; (2017); p. 5297 - 5300, View in Reaxys

2

Bhattacharjee, Suchandra; Khan, Abu T.; Tetrahedron Letters; vol. 57; nb. 27-28; (2016); p. 2994 - 2997, View in Reaxys

5

Yang, Changjiang; Liu, Wei; He, Zijian; He, Zhengjie; Organic Letters; vol. 18; nb. 19; (2016); p. 4936 4939, View in Reaxys

2d

Keene, Craig; Kuerti, Laszlo; Synthesis (Germany); vol. 45; nb. 13; (2013); p. 1719 - 1729; Art.No: SS-2013-C0260-FA, View in Reaxys; Acosta, Paola; Becerra, Diana; Goudedranche, Sébastien; Quiroga, Jairo; Constantieux, Thierry; Bonne, Damien; Rodriguez, Jean; Synlett; vol. 26; nb. 11; (2015); p. 1591 - 1595; Art.No: ST-2015-B0154-L, View in Reaxys

2i

Naciuk, Fabricio F.; Vargas, Debora Z.; D'oca, Caroline R. M.; Moro, Celso C.; Russowsky, Dennis; New Journal of Chemistry; vol. 39; nb. 3; (2015); p. 1643 - 1653, View in Reaxys

5e

Flores-Ferrndiz, Jess; Stiven, Alexander; Sotorros, Lia; Gmez-Bengoa, Enrique; Chinchilla, Rafael; Tetrahedron Asymmetry; vol. 26; nb. 17; (2015); p. 970 - 979; Art.No: 59347, View in Reaxys

3e

Balachandra, Biguvu; Shanmugam, Sivakumar; Muneeswaran, Thillaichidambaram; Ramakritinan, Muthiah; RSC Advances; vol. 5; nb. 79; (2015); p. 64781 - 64789, View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2c

Rahmani-Nezhad, Samira; Safavi, Maliheh; Pordeli, Mahboobeh; Ardestani, Sussan Kabudanian; Khosravani, Leila; Pourshojaei, Yaghoub; Mahdavi, Mohammad; Emami, Saeed; Foroumadi, Alireza; Shafiee, Abbas; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 562 - 569, View in Reaxys

2m

Wu, Lei; Li, Guangxun; Fu, Qingquan; Yu, Luoting; Tang, Zhuo; Organic and Biomolecular Chemistry; vol. 11; nb. 3; (2013); p. 443 - 447, View in Reaxys

27

Bourry, Anne; Pitard, Franck; Rigo, Benoit; Sanz, Gerard; Camus, Fabrice; Norberg, Bernadette; Durant, Francois; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 39; nb. 1; (2002); p. 109 - 118, View in Reaxys

2e (R3=H, R4,5,6=OCH3)

Brahmbhatt; Hirani; Pandya; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 3; (2000); p. 233 - 235, View in Reaxys

1. intermed. to 4

Silveira, Claudio C.; Bernardi, Carmem R.; Braga, Antonio L.; Kaufman, Teodoro S.; Tetrahedron Letters; vol. 40; nb. 27; (1999); p. 4969 - 4972, View in Reaxys

5c

Bobowski; West; Omecinsky; Journal of Heterocyclic Chemistry; vol. 29; nb. 1; (1992); p. 33 - 49, View in Reaxys

13

Kohno; Sasao; Murahashi; Bulletin of the Chemical Society of Japan; vol. 63; nb. 4; (1990); p. 1252 - 1254, View in Reaxys

11h

Hassner, Alfred; Dehaen, Wim; Journal of Organic Chemistry; vol. 55; nb. 20; (1990); p. 5505 - 5510, View in Reaxys

3

Tischer, Thomas; Toke, Laszlo; Toth, Gabor; Acta Chimica Hungarica; vol. 127; nb. 2; (1990); p. 171 172, View in Reaxys

precursor of 1

Dauzonne; Royer; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 4; (1986); p. 1628 - 1633, View in Reaxys

prod.18

Aranda,G.; Chimica Therapeutica; vol. 6; (1971); p. 262 - 267, View in Reaxys

7, R=3,4,5(OMe)3

Seebach,D.; Leitz,H.F.; Angewandte Chemie; vol. 83; (1971); p. 542 - 544, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.974

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

5

TPSA

73.51

Lipinski Number

4

Veber Number

2

Melting Point (6) 1 of 6

Melting Point [°C]

120 - 123

Solvent (Melting Point)

isopropyl alcohol

Zheng, Can-Hui; Chen, Jun; Liu, Jia; Zhou, Xiao-Tian; Liu, Na; Shi, Duo; Huang, Jing-Jing; Lv, Jia-Guo; Zhu, Ju; Zhou, You-Jun; Archiv der Pharmazie; vol. 345; nb. 6; (2012); p. 454 - 462, View in Reaxys 2 of 6

Melting Point [°C]

124 - 125

Solvent (Melting Point)

isopropyl alcohol

Mur Blanch, Nuria; Chabot, Guy G.; Quentin, Lionel; Scherman, Daniel; Bourg, Stephane; Dauzonne, Daniel; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 22 - 32, View in Reaxys 3 of 6

Melting Point [°C]

121 - 123

Rodriguez, Jose M.; Dolors Pujol; Tetrahedron Letters; vol. 52; nb. 21; (2011); p. 2629 - 2632, View in Reaxys 4 of 6

Melting Point [°C]

125.5 - 126.5

Solvent (Melting Point)

propan-2-ol

Dauzonne; Royer; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 4; (1986); p. 1628 - 1633, View in Reaxys 5 of 6

Melting Point [°C]

120 - 121

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Spaeth; Monatshefte fuer Chemie; vol. 40; (1919); p. 138; Monatshefte fuer Chemie; vol. 42; (1921); p. 263, View in Reaxys 6 of 6

Melting Point [°C]

119 - 120

Solvent (Melting Point)

ethanol

Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 92; (1915); p. 200, View in Reaxys Crystal Property Description (2) Colour & Other References Properties yellow

Zheng, Can-Hui; Chen, Jun; Liu, Jia; Zhou, Xiao-Tian; Liu, Na; Shi, Duo; Huang, Jing-Jing; Lv, JiaGuo; Zhu, Ju; Zhou, You-Jun; Archiv der Pharmazie; vol. 345; nb. 6; (2012); p. 454 - 462, View in Reaxys

gelbe Blaettchen oder Nadeln

Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 92; (1915); p. 200, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

1H

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

300

Mur Blanch, Nuria; Chabot, Guy G.; Quentin, Lionel; Scherman, Daniel; Bourg, Stephane; Dauzonne, Daniel; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 22 - 32, View in Reaxys; Qian, Wangke; Lu, Weijian; Sun, Haifeng; Li, Zeng; Zhu, Liyuan; Zhao, Rui; Zhang, Lei; Zhou, Shengbin; Zhou, Yu; Jiang, Hualiang; Zhen, Xuechu; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; nb. 15; (2012); p. 4862 - 4871, 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]

75

Mur Blanch, Nuria; Chabot, Guy G.; Quentin, Lionel; Scherman, Daniel; Bourg, Stephane; Dauzonne, Daniel; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 22 - 32, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

sodium chloride

Mur Blanch, Nuria; Chabot, Guy G.; Quentin, Lionel; Scherman, Daniel; Bourg, Stephane; Dauzonne, Daniel; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 22 - 32, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum

Mur Blanch, Nuria; Chabot, Guy G.; Quentin, Lionel; Scherman, Daniel; Bourg, Stephane; Dauzonne, Daniel; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 22 - 32, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation); Negative ion

Qian, Wangke; Lu, Weijian; Sun, Haifeng; Li, Zeng; Zhu, Liyuan; Zhao, Rui; Zhang, Lei; Zhou, Shengbin; Zhou, Yu; Jiang, Hualiang; Zhen, Xuechu; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; nb. 15; (2012); p. 4862 - 4871, View in Reaxys

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spectroscopy; Spectrum

Reaxys ID 9908449 View in Reaxys

3/3 Linear Structure Formula: C11H13NO5 Molecular Formula: C11H13NO5 Molecular Weight: 239.228 Type of Substance: isocyclic InChI Key: PEPYBEJQAIGLRE-PLNGDYQASA-N Note:

O O

Z O

O

N O

Substance Label (1) Label References 4a

Pradhan, Prasun K.; Dey, Sumit; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 35; nb. 7; (2005); p. 913 - 922, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.974

H Bond Donors

0

H Bond Acceptors

0

Rotatable Bonds

5

TPSA

73.51

Lipinski Number

4

Veber Number

2

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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