(1S, 2R)-{2-[(5-chloro-thiophene-2-carbonyl)-amino]-cyclopentyl}-carbamic acid tert-butyl ester | 630386-08-2

• 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: (1S, 2R)-{2-[(5-chloro-thiophene-2-carbonyl)-amino]-cyclopentyl}-carbamic acid tert-butyl ester
• 英文别名: (1S, 2R)-{2-[(5-chlorothiophene-2-carbonyl)amino]cyclopentyl}carbamic acid tert-butyl ester；tert-butyl N-[(1S,2R)-2-[(5-chlorothiophene-2-carbonyl)amino]cyclopentyl]carbamate
• CAS: 630386-08-2
• 化学式: C₁₅H₂₁ClN₂O₃S
• 分子量: 344.862
• InChiKey: DAVUDXAQOCAHER-ZJUUUORDSA-N

物化性质

• 沸点：
  500.6±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S, 2R)-{2-[(5-chloro-thiophene-2-carbonyl)-amino]-cyclopentyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 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-piperidin-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 、 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 (1S, 2R)-{2-[(5-chloro-thiophene-2-carbonyl)-amino]-cyclopentyl}-carbamic acid tert-butyl ester
  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

• [EN] 1,1-DISUBSTITUTED CYCLOALKYL DERIVATIVES AS FACTOR XA INHIBITORS<br/>[FR] DERIVES CYCLOALKYLES 1,1-DISUBSTITUES UTILISES EN TANT QU'INHIBITEURS DU FACTEUR XA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099276A1

  公开（公告）日：2003-12-04

  The present application describes 1,1-disubstituted cycloalkyl compounds and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.

  本申请描述了1,1-二取代环烷基化合物及其衍生物，或其药用可接受的盐形式，这些化合物对于Xa因子的抑制剂具有用处。
• [EN] LACTAM-CONTAINING CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS<br/>[FR] DIAMINES CYCLIQUES CONTENANT DU LACTAME ET LEURS DERIVES UTILISES EN TANT QU'INHIBITEURS DU FACTEUR XA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2004082687A1

  公开（公告）日：2004-09-30

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trysin-like serine proteases, specifically factor Xa.

  本申请描述了含有内酰胺的环状二胺及其衍生物的化合物，化学式如下：或其药用可接受的盐形式，其中M是非芳香族碳环或杂环。本发明的化合物可用作特异性抑制try sin-like丝氨酸蛋白酶，特别是Xa因子。
• Lactam-containing cyclic diamines and derivatives as factor Xa inhibitors
  申请人：——

  公开号：US20040204454A1

  公开（公告）日：2004-10-14

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: P 4 -M-M 4 I or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I：P4-M-M4I或其药学上可接受的盐形式的含有内酰胺的环状二胺及其衍生物，其中M是非芳香性碳环或杂环。本发明化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是因子Xa的抑制剂。
• LACTAM CONTAINING CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS
  申请人：Qiao X Jennifer

  公开号：US20070135428A1

  公开（公告）日：2007-06-14

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: P 4 -M-M 4 I or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I：P4-M-M4I或其药学上可接受的盐形式的含有内酰胺的环状二胺及其衍生物，其中M为非芳香族碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是Xa因子的抑制剂。
• US7205318B2
  申请人：——

  公开号：US7205318B2

  公开（公告）日：2007-04-17