N-[(1R,2S)-2-aminocyclopentyl]-3,4-dichlorobenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(1R,2S)-2-aminocyclopentyl]-3,4-dichlorobenzamide
• 化学式: C₁₂H₁₄Cl₂N₂O
• 分子量: 273.162
• InChiKey: DYBLEHREQZNCEE-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-[(1R,2S)-2-aminocyclopentyl]-3,4-dichlorobenzamide 、 4-(2-oxopyridin-1(2H)-yl)benzoic acid 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S)-3,4-dichloro-phenyl-carboxylic acid {2-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-cyclopentyl}-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：

  (1S,2S)-反式-N-BOC-2-氨基环戊醇 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-aminocyclopentyl]-3,4-dichlorobenzamide
  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

文献信息

• SAR and X-ray structures of enantiopure 1,2-cis-(1R,2S)-cyclopentyldiamine and cyclohexyldiamine derivatives as inhibitors of coagulation Factor Xa
  作者：Jennifer X. Qiao、Chong-Hwan Chang、Daniel L. Cheney、Paul E. Morin、Gren Z. Wang、Sarah R. King、Tammy C. Wang、Alan R. Rendina、Joseph M. Luettgen、Robert M. Knabb、Ruth R. Wexler、Patrick Y.S. Lam

  DOI：10.1016/j.bmcl.2007.06.029

  日期：2007.8

  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.