2-(acetylthio)cyclopentanecarboxylic acid | 80969-54-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: 2-(acetylthio)cyclopentanecarboxylic acid
• 英文别名: (2-acetylthio)-cyclopentane carboxylic acid；2-Acetylsulfanylcyclopentane-1-carboxylic acid
• CAS: 80969-54-6
• 化学式: C₈H₁₂O₃S
• 分子量: 188.247
• InChiKey: KBWPBCUGEVTNKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-(acetylthio)cyclopentanecarboxylic acid 在 sodium hydroxide 、 氯化亚砜 作用下， 反应 34.0h， 生成 1-<<2-(acetylthio)cyclopentyl>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：

  1-环戊烯-1-甲酸乙酯 、 1-环戊烯羧酸 、 硫代乙酸 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 2-(acetylthio)cyclopentanecarboxylic acid
  参考文献：
  名称：

  1-[(-2-Mercaptocycloalkyl)carbonyl]-L-proline derivatives, the process

  摘要：

  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。

  公开号：

  US04385062A1

文献信息

• PYRROLIDINE AND THIAZOLE DERIVATIVES WITH METALLO-BETA-LACTAMASE INHIBITORY PROPERTIES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0970062A2

  公开（公告）日：2000-01-12
• US4385062A
  申请人：——

  公开号：US4385062A

  公开（公告）日：1983-05-24
• US4496743A
  申请人：——

  公开号：US4496743A

  公开（公告）日：1985-01-29
• [EN] PYRROLIDINE AND THIAZOLE DERIVATIVES WITH METALLO-BETA-LACTAMASE INHIBITORY PROPERTIES<br/>[FR] DERIVES DE PYRROLIDINE ET THIAZOLE AUX PROPRIETES INHIBANT LA BETA-LACTAMASE METALLIQUE
  申请人：——

  公开号：WO1998040056A2

  公开（公告）日：1998-09-17

  [EN] A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a beta -lactam antibiotic, a therapeutically effective amount of an amino acid derivative or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof.
  [FR] Méthode de traitement d'infections bactériennes chez les humains et les animaux consiste à administrer, en association avec une beta -lactamine, une quantité thérapeutiquement efficace d'un dérivé d'acide aminé ou un sel pharmaceutiquement acceptable, un solvate ou un ester hydrolysable in vivo de ce dernier.
• 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.