[2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-acetic acid | 666817-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-acetic acid
• 英文别名: [2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetic acid；2-[2-(5-chlorothiophen-2-yl)-3H-benzimidazol-5-yl]acetic acid
• CAS: 666817-40-9
• 化学式: C₁₃H₉ClN₂O₂S
• 分子量: 292.746
• InChiKey: XDSQHQMKKUKCEX-UHFFFAOYSA-N

物化性质

• 沸点：
  565.3±60.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氨基苯基)吗啡啉-3-酮 、 [2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-acetic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-N-[4-(3-oxo-morpholin-4-yl)-phenyl]-acetamide
  参考文献：
  名称：

  Halothiophene benzimidazoles as P1 surrogates of inhibitors of blood coagulation factor Xa

  摘要：

  Neutral weak halothiophene benzimidazole inhibitors of the serine protease factor Xa were identified via screening of a compound library. The X-ray crystal structure of representative 3a bound to human fXa confirmed the S1 binding mode. Starting from 3a a series of halothiophene benzimidazoles was synthesized and investigated for their factor Xa inhibitory activity. This led to potent and selective achiral inhibitors against fXa such as compounds 9k and 9w. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.097
• 作为产物：
  描述：

  5-氯噻吩-2-甲醛 在 sodium hydroxide 、 sodium hydrogensulfite 作用下， 以 N-甲基吡咯烷酮 、 甲醇 为溶剂， 生成 [2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-acetic acid
  参考文献：
  名称：

  Halothiophene benzimidazoles as P1 surrogates of inhibitors of blood coagulation factor Xa

  摘要：

  Neutral weak halothiophene benzimidazole inhibitors of the serine protease factor Xa were identified via screening of a compound library. The X-ray crystal structure of representative 3a bound to human fXa confirmed the S1 binding mode. Starting from 3a a series of halothiophene benzimidazoles was synthesized and investigated for their factor Xa inhibitory activity. This led to potent and selective achiral inhibitors against fXa such as compounds 9k and 9w. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.097

文献信息

• Benzimidazole derivatives
  申请人：Dorsch Dieter

  公开号：US20050272740A1

  公开（公告）日：2005-12-08

  Novel compounds of the formula I in which D, X, X′, W, Y, T and R 1 are as defined in Patent claim 1, are inhibitors of coagulation factor Xa and can be employed for the prophylaxis and/or therapy of thromboembolic diseases and for the treatment of tumours.

  公式I中的新化合物，其中D、X、X'、W、Y、T和R1如专利申请1所定义，是凝血因子Xa的抑制剂，可用于预防和/或治疗血栓性疾病以及治疗肿瘤。
• BENZIMIDAZOLDERIVATE
  申请人：MERCK PATENT GmbH

  公开号：EP1558247A1

  公开（公告）日：2005-08-03
• US7566789B2
  申请人：——

  公开号：US7566789B2

  公开（公告）日：2009-07-28
• [DE] BENZIMIDAZOLDERIVATE<br/>[EN] BENZIMIDAZOLE DERIVATIVES<br/>[FR] DERIVES DE BENZIMIDAZOLE
  申请人：MERCK PATENT GMBH

  公开号：WO2004017963A1

  公开（公告）日：2004-03-04

  Neue verbindungen der formel I Wori D, X, X‘, W, Y, T und R1 die in patentanspruch 1 angegebene Bedeutung haben, Sind inhibitoren des koagulationsfaktors Xa und können zur Prophylaxe und/oder Terapie von thromboembolischen Erkrankungen und zur Behandlung von tumoren eingesetzt werden.
• Halothiophene benzimidazoles as P1 surrogates of inhibitors of blood coagulation factor Xa
  作者：Werner W.K.R Mederski、Dieter Dorsch、Soheila Anzali、Johannes Gleitz、Bertram Cezanne、Christos Tsaklakidis

  DOI：10.1016/j.bmcl.2004.04.097

  日期：2004.7

  Neutral weak halothiophene benzimidazole inhibitors of the serine protease factor Xa were identified via screening of a compound library. The X-ray crystal structure of representative 3a bound to human fXa confirmed the S1 binding mode. Starting from 3a a series of halothiophene benzimidazoles was synthesized and investigated for their factor Xa inhibitory activity. This led to potent and selective achiral inhibitors against fXa such as compounds 9k and 9w. (C) 2004 Elsevier Ltd. All rights reserved.