cis-2-(benzoylthio)cyclopentanecarboxylic acid | 99397-53-2

• 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: cis-2-(benzoylthio)cyclopentanecarboxylic acid
• 英文别名: (1S,2S)-2-benzoylsulfanylcyclopentane-1-carboxylic acid
• CAS: 99397-53-2
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: AIFPEAAIIWMBNU-MNOVXSKESA-N

物化性质

• 沸点：
  416.7±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-2-(benzoylthio)cyclopentanecarboxylic acid 在 ammonium hydroxide 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 <1S,2S>-1-<(2-mercaptocyclopentyl)carbonyl>-L-proline
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors as antihypertensive agents: 1-[(2-mercaptocycloalkyl)carbonyl]-L-prolines

  摘要：

  The synthesis of 1-[(2-mercaptocyclopentyl)carbonyl]-L-prolines, 1-[(2-mercaptocyclobutyl)carbonyl]-L-prolines and related benzoyl derivatives as pure isomers is described. The abilities of all the compounds to inhibit angiotensin converting enzyme (ACE) in vitro and in vivo and to lower the systolic blood pressure in renal hypertensive dogs were determined. Three of them, namely 1-[[2-(benzoylthio)cyclopentyl]carbonyl]-L-proline (10f(R,S], 1-[(2-mercaptocyclopentyl)carbonyl]-L-proline (10g(R,S], and 1-[[2-(benzoylthio)cyclobutyl]carbonyl]-L-proline (16f(R,S], were found to be as potent as captopril in reducing blood pressure. The influence of chirality and ring size on the ACE inhibition is described.

  DOI：

  10.1021/jm00153a017
• 作为产物：
  描述：

  2-甲氧羰基环戊酮 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 cis-2-(benzoylthio)cyclopentanecarboxylic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors as antihypertensive agents: 1-[(2-mercaptocycloalkyl)carbonyl]-L-prolines

  摘要：

  The synthesis of 1-[(2-mercaptocyclopentyl)carbonyl]-L-prolines, 1-[(2-mercaptocyclobutyl)carbonyl]-L-prolines and related benzoyl derivatives as pure isomers is described. The abilities of all the compounds to inhibit angiotensin converting enzyme (ACE) in vitro and in vivo and to lower the systolic blood pressure in renal hypertensive dogs were determined. Three of them, namely 1-[[2-(benzoylthio)cyclopentyl]carbonyl]-L-proline (10f(R,S], 1-[(2-mercaptocyclopentyl)carbonyl]-L-proline (10g(R,S], and 1-[[2-(benzoylthio)cyclobutyl]carbonyl]-L-proline (16f(R,S], were found to be as potent as captopril in reducing blood pressure. The influence of chirality and ring size on the ACE inhibition is described.

  DOI：

  10.1021/jm00153a017

文献信息

• 1-[(-2-Mercaptocycloalkyl)carbonyl]-L-proline derivatives, the process
  申请人：Gruppo Lepetit S.p.A.

  公开号：US04385062A1

  公开（公告）日：1983-05-24

  1-[(2-Mercaptocycloalkyl)carbonyl]-L-proline derivatives of the formula ##STR1## wherein R, R.sup.1, and R.sup.2, each independently, represent hydrogen or a (C.sub.1 -C.sub.4)alkyl radical, n represents the integer 1, 2, 3, 4, or 5, and, in each of the n (CR'.sub.2) groups, R' represents hydrogen or (C.sub.1 -C.sub.4)alkyl, are described as well as the process for their manufacture, the intermediates for their synthesis and their use as antihypertensive agents.

  该文描述了公式## STR1##的1-[(2-巯基环烷基)羰基]-L-脯氨酸衍生物，其中R、R.sup.1和R.sup.2，各自独立地表示氢或(C.sub.1-C.sub.4)烷基基团，n表示整数1、2、3、4或5，在n个(CR'.sub.2)基团中，R'表示氢或(C.sub.1-C.sub.4)烷基。此外，还描述了它们的制造过程、合成的中间体以及它们作为降压剂的用途。
• Angiotensin converting enzyme inhibitors as antihypertensive agents: 1-[(2-mercaptocycloalkyl)carbonyl]-L-prolines
  作者：Romeo Ciabatti、Giovanna Padova、Elvio Bellasio、Giorgio Tarzia、Adele Depaoli、Franco Battaglia、Mario Cellentani、Domenico Barone、Emiliana Baldoli

  DOI：10.1021/jm00153a017

  日期：1986.3

  The synthesis of 1-[(2-mercaptocyclopentyl)carbonyl]-L-prolines, 1-[(2-mercaptocyclobutyl)carbonyl]-L-prolines and related benzoyl derivatives as pure isomers is described. The abilities of all the compounds to inhibit angiotensin converting enzyme (ACE) in vitro and in vivo and to lower the systolic blood pressure in renal hypertensive dogs were determined. Three of them, namely 1-[[2-(benzoylthio)cyclopentyl]carbonyl]-L-proline (10f(R,S], 1-[(2-mercaptocyclopentyl)carbonyl]-L-proline (10g(R,S], and 1-[[2-(benzoylthio)cyclobutyl]carbonyl]-L-proline (16f(R,S], were found to be as potent as captopril in reducing blood pressure. The influence of chirality and ring size on the ACE inhibition is described.