3-[2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-propionic acid | 742073-13-8

• 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: 3-[2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-propionic acid
• 英文别名: 3-[2-(5-chlorothiophen-2-yl)-3H-benzimidazol-5-yl]propanoic acid
• CAS: 742073-13-8
• 化学式: C₁₄H₁₁ClN₂O₂S
• 分子量: 306.773
• InChiKey: GWMDOODXYNCUDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.98
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(3-oxo-morpholin-4-yl)-aniline 、 3-[2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-propionic 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 N-[3-Chloro-4-(3-oxo-morpholin-4-yl)-phenyl]-3-[2-(5-chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-propionamide
  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：

  3-(3,4-Diamino-phenyl)-propionic acid ethyl ester 在 sodium hydroxide 、 sodium hydrogensulfite 作用下， 以 N-甲基吡咯烷酮 、 甲醇 为溶剂， 反应 14.0h， 生成 3-[2-(5-Chloro-thiophen-2-yl)-1H-benzoimidazol-5-yl]-propionic 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