[(2-Acetylsulfanyl-3-isopropyl-benzoyl)-cyclopentyl-amino]-acetic acid | 92399-66-1

• 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: [(2-Acetylsulfanyl-3-isopropyl-benzoyl)-cyclopentyl-amino]-acetic acid
• 英文别名: 2-[(2-acetylsulfanyl-3-propan-2-ylbenzoyl)-cyclopentylamino]acetic acid
• CAS: 92399-66-1
• 化学式: C₁₉H₂₅NO₄S
• 分子量: 363.478
• InChiKey: BGDRAIJPQRHWCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2-Acetylsulfanyl-3-isopropyl-benzoyl)-cyclopentyl-amino]-acetic acid 在 sodium hydroxide 作用下， 反应 2.0h， 以100%的产率得到[Cyclopentyl-(3-isopropyl-2-mercapto-benzoyl)-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids

  摘要：

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.

  DOI：

  10.1021/jm00381a012
• 作为产物：
  描述：

  N-环戊基甘氨酸叔丁酯 在 三甲基氯硅烷 、 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 [(2-Acetylsulfanyl-3-isopropyl-benzoyl)-cyclopentyl-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids

  摘要：

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.

  DOI：

  10.1021/jm00381a012

文献信息

• Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids
  作者：Paul R. Menard、John T. Suh、Howard Jones、Bernard Loev、Edward S. Neiss、Joyce Wilde、Alfred Schwab、William S. Mann

  DOI：10.1021/jm00381a012

  日期：1985.3

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.