N-[(1R,2S)-2-aminocyclohexyl]-5-chlorothiophene-2-carboxamide | 950677-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N-[(1R,2S)-2-aminocyclohexyl]-5-chlorothiophene-2-carboxamide
• CAS: 950677-99-3
• 化学式: C₁₁H₁₅ClN₂OS
• 分子量: 258.772
• InChiKey: RDTQSVQMUNAMJC-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[(1R,2S)-2-aminocyclohexyl]-5-chlorothiophene-2-carboxamide 、 4-(2-oxopyridin-1(2H)-yl)benzoic acid 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1R, 2S)-5-chloro-thiophene-2-carboxylic acid {2-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-cyclohexyl}-amide
  参考文献：
  名称：

  SAR and X-ray structures of enantiopure 1,2-cis-(1R,2S)-cyclopentyldiamine and cyclohexyldiamine derivatives as inhibitors of coagulation Factor Xa

  摘要：

  In the search of Factor Xa (FXa) inhibitors structurally different from the pyrazole-based series, we identified a viable series of enantiopure cis-(1R,2S)-cycloalkyldiamine derivatives as potent and selective inhibitors of FXa. Among them, cyclohexyldiamide 7 and cyclopentyldiamide 9 were the most potent neutral compounds, and had good anticoagulant activity comparable to the pyrazole-based analogs. Crystal structures of 7-FXa and 9-FXa illustrate binding similarities and differences between the five-and the six-membered core systems, and provide rationales for the observed SAR of PI and linker moieties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.029
• 作为产物：
  描述：

  N-((2S,1S)-2-羟基环己基)氨基甲酸叔丁酯 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-[(1R,2S)-2-aminocyclohexyl]-5-chlorothiophene-2-carboxamide
  参考文献：
  名称：

  SAR and X-ray structures of enantiopure 1,2-cis-(1R,2S)-cyclopentyldiamine and cyclohexyldiamine derivatives as inhibitors of coagulation Factor Xa

  摘要：

  In the search of Factor Xa (FXa) inhibitors structurally different from the pyrazole-based series, we identified a viable series of enantiopure cis-(1R,2S)-cycloalkyldiamine derivatives as potent and selective inhibitors of FXa. Among them, cyclohexyldiamide 7 and cyclopentyldiamide 9 were the most potent neutral compounds, and had good anticoagulant activity comparable to the pyrazole-based analogs. Crystal structures of 7-FXa and 9-FXa illustrate binding similarities and differences between the five-and the six-membered core systems, and provide rationales for the observed SAR of PI and linker moieties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.029