Query Query
Results
Date
1 substances in Reaxys
2017-10-28 13h:13m:57s (EST)
O
1. Query
O
Search as: As drawn
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.
1/7
2017-10-28 13:14:52
Reaxys ID 124062 View in Reaxys
1/1 CAS Registry Number: 55745-70-5 Chemical Name: 2,3-dihydro-benzofuran-5-carbaldehyde; 5benzofuran carboxaldehyde Linear Structure Formula: C9H8O2 Molecular Formula: C9H8O2 Molecular Weight: 148.161 Type of Substance: heterocyclic InChI Key: WEBVDBDZSOJGPB-UHFFFAOYSA-N Note:
O O
Substance Label (27) Label References 2
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/93719; (2006); (A1) English, View in Reaxys; Lemaire, Sebastien; Willemsens, Bert; Marko, Istvan E.; Synlett; nb. 5; (2007); p. 709 - 712, View in Reaxys; Chen, Wen; Yang, Li-Juan; Li, Yan; Wang, Xue-Quan; Wang, Shao-Jie; Wan, Wei-Chao; Zhang, HongBin; Yang, Xiao-Dong; Letters in Drug Design and Discovery; vol. 10; nb. 7; (2013); p. 561 - 571, View in Reaxys; Patent; Yunnan University; Yang Xiaodong; Zhang Hongbin; Chen Wen; Wang Xuequan; Yang Lijuan; Li Liang; (38 pag.); CN102766135; (2017); (B) Chinese, View in Reaxys
8
Ferguson, Jalisa; De Los Santos, Zeus; Devi, Narra; Van Meir, Erwin; Zingales, Sarah; Wang, Binghe; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 8; (2017); p. 1731 - 1736, View in Reaxys
2r
Zhang, Muliang; Li, Nan; Tao, Xingyu; Ruzi, Rehanguli; Yu, Shouyun; Zhu, Chengjian; Chemical Communications; vol. 53; nb. 73; (2017); p. 10228 - 10231, View in Reaxys
3
Jiang, Weiqin; Sui, Zhihua; Chen, Xin; Tetrahedron Letters; vol. 43; nb. 49; (2002); p. 8941 - 8945, View in Reaxys; Patent; USV LIMITED; SATHE, Dhananjay, Govind; BHISE, Nandu, Baban; GATNE, Parag, Sukumar; PATNEKAR, Subodh, Shashikant; DEORE, Raviraj, Bhatu; MAHAJAN, Anil, Dinkar; WO2010/41271; (2010); (A2) English, View in Reaxys; Zhang, Lianpeng; Lu, Ping; Wang, Yanguang; Organic and Biomolecular Chemistry; vol. 14; nb. 5; (2016); p. 1840 - 1840, View in Reaxys
5b
Chelli, Saloua; Troshin, Konstantin; Mayer, Peter; Lakhdar, Sami; Ofial, Armin R.; Mayr, Herbert; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10304 - 10313, View in Reaxys
Aldehyde-k
Patent; UNIVERSITY OF MYSORE; NATIONAL UNIVERSITY OF SINGAPORE; BANGALORE UNIVERSITY; CAMBRIDGE ENTERPRISE LTD; RANGAPPA, Kanchugarakoppal Subbegowda; BASAPPA; MOHAN, Chakrabhavi Dhananjaya; RANGAPPA, Shobith; BHARATHKUMAR, Hanumantharayappa; SETHI, Gautam; BENDER, Andreas; LOBIE, Peter Edward; HUI, Kam Man; KUMAR, Alan Prem; PANDEY, Vijay Kumar; FUCHS, Julian; SHANMUGAM, Muthu Kumaraswamy; BULUSU, Krishna; DAI, Xiaoyun; LI, Feng; DEIVASIGAMANI, Amudha; (28 pag.); US2016/214968; (2016); (A1) English, View in Reaxys
2t
Du, Guang-Fen; Wang, Ying; Gu, Cheng-Zhi; Dai, Bin; He, Lin; RSC Advances; vol. 5; nb. 45; (2015); p. 35421 - 35424, View in Reaxys
3(20)
Ryabukhin, Sergey V.; Panov, Dmitriy M.; Granat, Dmitry S.; Ostapchuk, Eugeniy N.; Kryvoruchko, Dmitriy V.; Grygorenko, Oleksandr O.; ACS Combinatorial Science; vol. 16; nb. 3; (2014); p. 146 - 153, View in Reaxys
A
Patent; DUTTA, Aloke K.; US2014/309427; (2014); (A1) English, View in Reaxys
2e
Sun, Haifeng; Zhu, Liyuan; Yang, Huicui; Qian, Wangke; Guo, Lin; Zhou, Shengbin; Gao, Bo; Li, Zeng; Zhou, Yu; Jiang, Hualiang; Chen, Kaixian; Zhen, Xuechu; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 21; nb. 4; (2013); p. 856 - 868, View in Reaxys
29bl
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; CHINTAREDDY, Venkat, R.; WO2013/33093; (2013); (A1) English, View in Reaxys
107
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
12
Sewgobind, Nishant V.; Wanner, Martin J.; Ingemann, Steen; De Gelder, Rene; Van Maarseveen, Jan H.; Hiemstra, Henk; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6405 - 6408, View in Reaxys
II
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2008/151170; (2008); (A2) English, View in Reaxys
FBA
Patent; Takeda Pharmaceutical Company Limited; EP1792899; (2007); (A1) English, View in Reaxys
IX
Patent; TEVA PHARMACEUTICAL FINE CHEMICALS S.R.L.; TEVA PHARMACEUTICALS USA, INC.; WO2007/76157; (2007); (A2) English, View in Reaxys
Va
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/103754; (2007); (A2) English, 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.
2/7
2017-10-28 13:14:52
41(R=3,4OCH2CH2)
Borthwick, Alan D.; Davies, Dave E.; Exall, Anne M.; Hatley, Richard J. D.; Hughes, Jennifer A.; Irving, Wendy R.; Livermore, David G.; Sollis, Steve L.; Nerozzi, Fabrizio; Valko, Klara L.; Allen, Michael J.; Perren, Marion; Shabbir, Shalia S.; Woollard, Patrick M.; Price, Mark A.; Journal of Medicinal Chemistry; vol. 49; nb. 14; (2006); p. 4159 - 4170, View in Reaxys
subst., tab. 1, entry 4
Siu, Jason; Baxendale, Ian R.; Lewthwaite, Russell A.; Ley, Steven V.; Organic and Biomolecular Chemistry; vol. 3; nb. 17; (2005); p. 3140 - 3160, View in Reaxys
4
Li, Xun; Branum, Shawn; Russell, Ronald K.; Jiang, Weiqin; Sui, Zhihua; Organic Process Research and Development; vol. 9; nb. 5; (2005); p. 640 - 645, View in Reaxys
50
Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro; Bioorganic and Medicinal Chemistry; vol. 12; nb. 16; (2004); p. 4313 - 4336, View in Reaxys
3b
Jiang, Weiqin; Alford, Vernon C.; Qiu, Yuhong; Bhattacharjee, Sheela; John, T. Matthew; HaynesJohnson, Donna; Kraft, Patricia J.; Lundeen, Scott G.; Sui, Zhihua; Bioorganic and Medicinal Chemistry; vol. 12; nb. 6; (2004); p. 1505 - 1515, View in Reaxys
2, R=3,4CH2CH2O-
Sui, Zhihua; Guan, Jihua; Macielag, Mark J.; Jiang, Weiqin; Qiu, Yuhong; Kraft, Patricia; Bhattacharjee, Sheela; John, T. Matthew; Craig, Elizabeth; Haynes-Johnson, Donna; Clancy, Joanna; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 4; (2003); p. 761 - 765, View in Reaxys
11b
Jiang, Weiqin; Sui, Zhihua; Macielag, Mark J.; Walsh, Shawn P.; Fiordeliso, James J.; Lanter, James C.; Guan, Jihua; Qiu, Yuhong; Kraft, Patricia; Bhattacharjee, Sheela; Craig, Elizabeth; Haynes-Johnson, Donna; John, T. Matthew; Clancy, Joanna; Journal of Medicinal Chemistry; vol. 46; nb. 3; (2003); p. 441 - 444, View in Reaxys
6
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori; Journal of Medicinal Chemistry; vol. 45; nb. 19; (2002); p. 4222 - 4239, View in Reaxys
product run 6
Plotkin, Michael; Chen, Sanyou; Spoors, P. Grant; Tetrahedron Letters; vol. 41; nb. 14; (2000); p. 2269 2273, View in Reaxys
educt to 3a
Coleman, Paul J.; Hutchinson, John H.; Hunt, Cecilia A.; Lu, Ping; Delaporte, Enock; Rushmore, Tom; Tetrahedron Letters; vol. 41; nb. 31; (2000); p. 5803 - 5806, View in Reaxys
Patent-Specific Data (4) 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; SMITHKLINE BEECHAM CORPORATION; WO2007/103754; (2007); (A2) English, View in Reaxys
Claim
Patent; L'Oreal S.A.; US6451067; (2002); (B1) English, View in Reaxys; Patent; L'Oreal, S.A.; US6635090; (2003); (B1) English, View in Reaxys; Patent; L'Oreal S.A.; US6458168; (2002); (B1) English, View in Reaxys Patent; Takeda Chemical Industries, Ltd.; EP1199304; (2002); (A1) English, View in Reaxys
Druglikeness (1) 1 of 1
LogP
1.479
H Bond Donors
0
H Bond Acceptors
1
Rotatable Bonds
1
TPSA
26.3
Lipinski Number
4
Veber Number
2
Boiling Point (3) Boiling Point [°C] 93 - 96
Pressure (Boiling Point) [Torr]
References
0.2 - 0.3
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori; Journal of Medicinal Chemistry; vol. 45; nb. 19; (2002); p. 4222 - 4239, 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.
3/7
2017-10-28 13:14:52
110 - 112
1.5
Kelly, David P.; Jenkins, Margot J.; Journal of Organic Chemistry; vol. 49; nb. 3; (1984); p. 409 - 413, View in Reaxys
140 - 142
8
Baddeley et al.; Journal of the Chemical Society; (1956); p. 2455,246, View in Reaxys
Crystal Property Description (2) Colour & Other Location Properties yellow
supporting information
colourless
References Chelli, Saloua; Troshin, Konstantin; Mayer, Peter; Lakhdar, Sami; Ofial, Armin R.; Mayr, Herbert; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10304 - 10313, View in Reaxys Chen, Wen; Yang, Li-Juan; Li, Yan; Wang, Xue-Quan; Wang, Shao-Jie; Wan, WeiChao; Zhang, Hong-Bin; Yang, Xiao-Dong; Letters in Drug Design and Discovery; vol. 10; nb. 7; (2013); p. 561 - 571, View in Reaxys
NMR Spectroscopy (8) 1 of 8
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Chelli, Saloua; Troshin, Konstantin; Mayer, Peter; Lakhdar, Sami; Ofial, Armin R.; Mayr, Herbert; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10304 - 10313, View in Reaxys; Zhang, Muliang; Li, Nan; Tao, Xingyu; Ruzi, Rehanguli; Yu, Shouyun; Zhu, Chengjian; Chemical Communications; vol. 53; nb. 73; (2017); p. 10228 - 10231, View in Reaxys 2 of 8
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Zhang, Muliang; Li, Nan; Tao, Xingyu; Ruzi, Rehanguli; Yu, Shouyun; Zhu, Chengjian; Chemical Communications; vol. 53; nb. 73; (2017); p. 10228 - 10231, View in Reaxys 3 of 8
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100.6
Location
supporting information
Chelli, Saloua; Troshin, Konstantin; Mayer, Peter; Lakhdar, Sami; Ofial, Armin R.; Mayr, Herbert; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10304 - 10313, View in Reaxys 4 of 8
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
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.
4/7
2017-10-28 13:14:52
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori; Journal of Medicinal Chemistry; vol. 45; nb. 19; (2002); p. 4222 - 4239, View in Reaxys; Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro; Bioorganic and Medicinal Chemistry; vol. 12; nb. 16; (2004); p. 4313 - 4336, View in Reaxys 5 of 8
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori; Journal of Medicinal Chemistry; vol. 45; nb. 19; (2002); p. 4222 - 4239, View in Reaxys; Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro; Bioorganic and Medicinal Chemistry; vol. 12; nb. 16; (2004); p. 4313 - 4336, View in Reaxys 6 of 8
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Location
Page 68
Comment (NMR Spectroscopy)
Signals given
Patent; Takeda Chemical Industries, Ltd.; EP1199304; (2002); (A1) English, View in Reaxys 7 of 8
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 36; nb. 23; (1993); p. 3700 - 3706, View in Reaxys 8 of 8
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Kelly, David P.; Jenkins, Margot J.; Journal of Organic Chemistry; vol. 49; nb. 3; (1984); p. 409 - 413, View in Reaxys IR Spectroscopy (2) 1 of 2
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
1686 cm**(-1)
Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 36; nb. 23; (1993); p. 3700 - 3706, View in Reaxys 2 of 2
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
1680 cm**(-1)
Kelly, David P.; Jenkins, Margot J.; Journal of Organic Chemistry; vol. 49; nb. 3; (1984); p. 409 - 413, 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.
5/7
2017-10-28 13:14:52
Medchem (2) 1 of 2
Target Mutant/Chimera Details
Cytochrome P450 2E1 [human]:Wild
Target Species (Bioactivity)
human
Target Subunit Proteins
Cytochrome P450 2E1 [human]
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibitory concentration of compound against recombinant human CYTOCHROME P450 2E1 expressed in insect cells using baculovirus expression system upon incubation in 100 mM TRIS-HCl, pH 7.4 at 37 degree C for 40 minutes using 10 uM 7-METHOXY-4-TRIFLUOROMETHYLCOUMARIN as substrate
Biological Species/NCBI Human ID Substance RN
124062View in Reaxys
Measurement Parameter
IC50
Unit
µM
Qualitative value
=
Quantitative value
7.7
Measurement pX
5.11
Target, Subunit, Species Cytochrome P450 2E1 [human]
2 of 2
Target Subunit Synonyms
4-nitrophenol 2-hydroxylase; cyp2e; cyp2e1 (cytochrome p450 2e1); cypiie1; cytochrome p450 2e1; cytochrome p450-j
Target Uniprot ID
p05181
Target PDB ID
3e4e; 3e6i; 3gph; 3koh; 3lc4; 3t3z
Compound name
7-METHOXY-4-TRIFLUOROMETHYLCOUMARIN
Compound role
SUB
Target Mutant/Chimera Details
Pteridine reductase 1 [Leishmania major]:Wild
Substance Action on Target
Inhibitor
Target Species (Bioactivity)
Leishmania major
Target Subunit Proteins
Pteridine reductase 1 [Leishmania major]
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Percent inhibition against Leishmania major pteridine reductase 1 at a compound concentration (dissolved in DMSO) of 500 uM
Biological Species/NCBI Leishmania major ID Substance RN
124062View in Reaxys
Qualitative Results
NI = No inhibition
Measurement Parameter
Activity
Qualitative value
NA
Measurement pX
1
Target, Subunit, Species Pteridine reductase 1 [Leishmania major] Target Subunit Synonyms
h region methotrexate resistance protein; hmtxr; l1063.01; lmjf23.0270; lmjf_23_0270; pteridine reductase 1; ptr1
Target Uniprot ID
q01782
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.
6/7
2017-10-28 13:14:52
Target PDB ID
1e7w; 1e92; 1w0c; 2bf7; 2bfa; 2bfm; 2bfo; 2bfp; 2qhx; 3h4v
Measurement Object
Inhibition
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.
7/7
2017-10-28 13:14:52