N-(2-Mercapto-3-methylbenzoyl)-N-cyclopentylglycine | 83596-86-5

• 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-(2-Mercapto-3-methylbenzoyl)-N-cyclopentylglycine
• 英文别名: 2-[cyclopentyl-(3-methyl-2-sulfanylbenzoyl)amino]acetic acid
• CAS: 83596-86-5
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: HENWJMDWNWIQHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine t-butyl ester 在 三甲基氯硅烷 、 氨 、 sodium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.83h， 生成 N-(2-Mercapto-3-methylbenzoyl)-N-cyclopentylglycine
  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

• Aroyl-aminoacids, amides and esters thereof
  申请人：USV Pharmaceutical Corporation

  公开号：US04440941A1

  公开（公告）日：1984-04-03

  Compounds of the structure ##STR1## wherein: Q is oxygen, sulfur or imino. X and Y are hydrogen, halogen, hydroxy, alkoxy, trifluoromethyl, nitro, carboxy, cyano, sulfonamido, sulfhydryl, alkyl, alkenyl, alkynyl, alkanoyl, alkylmercapto, amino, alkylamino, dialkylamino, alkysulfinyl, and alkylsulfonyl and may be the same or different; R.sub.1 is hydrogen, alkanoyl, substituted alkanoyl wherein the substituent is hydroxy, amino or cycloalkyl, aroyl, arylalkanoyl, or cycloalkylcarbonyl, n is an integer from 1 to 4 inclusive, R.sub.2 and R.sub.3 are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, aryl, aralkyl, and substituted derivatives thereof wherein the substituents are hydroxy, amino, alkylamino, dialkylamino, alkoxy, halogen, hydroxy, mercapto, alkylmercapto and nitro, and may be the same or different; M is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, and hetero; and Z is hydroxy, amino, alkylamino, dialkylamino, or alkoxy, have angiotensin converting enzyme inhibitory activity.

  结构式为##STR1##的化合物，其中：Q为氧、硫或亚胺。X和Y为氢、卤素、羟基、烷氧基、三氟甲基、硝基、羧基、氰基、磺酰胺基、硫醇基、烷基、烯基、炔基、酰基、烷硫基、氨基、烷基氨基、二烷基氨基、烷基亚磺酰基和烷基磺酰基，可以相同也可以不同；R.sub.1为氢、烷酰基、取代烷酰基，其中取代基为羟基、氨基或环烷基、芳酰基、芳基烷酰基或环烷基羧酰基，n为1到4的整数，包括1和4，R.sub.2和R.sub.3为氢、烷基、烯基、炔基、环烷基、环烷基-烷基、芳基、芳基烷基和取代衍生物，其中取代基为羟基、氨基、烷基氨基、二烷基氨基、烷氧基、卤素、羟基、巯基、烷硫基和硝基，可以相同也可以不同；M为烷基、烯基、炔基、环烷基、环烷基烷基、芳基、芳基烷基和杂环基；Z为羟基、氨基、烷基氨基、二烷基氨基或烷氧基，具有血管紧张素转换酶抑制活性。
• Aroyl amino acids
  申请人：USV PHARMACEUTICAL CORPORATION

  公开号：EP0054936A1

  公开（公告）日：1982-06-30

  This invention relates to new chemical compounds possessing valuable pharmaceutical activity. It particularly relates to compounds possessing antihypertensive and angiotensin converting enzyme inhibitory activity and having the structure: wherein: Q is oxygen, sulfur or NH; X and Y are hydrogen, halogen, hydroxy, alkoxy, trifluoromethyl, nitro, carboxy, cyano, sulfonamido, sulfhydryl, alkyl, alkenyl, alkynyl, alkanoyl, alkylmercapto, amino, alkylamino, dialkylamino, alkylsulfinyl, and alkylsulfonyl and may be the same or different; R, is hydrogen, alkanoyl, substituted alkanoyl wherein the substituent is hydroxy, amino or cycloalkyl, aroyl, arylakanoyl, or cycloalkylcarbonyl, n is an integer from to 4 inclusive, R2 and R3 are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, aryl, aralkyl, and substituted derivatives thereof wherein the substituents are hydroxy, amino, alkylamino, dialkylamino, alkoxy, halogen, hydroxy, mercapto, alkylmercapto and nitro, and may be the same or different; M is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, aryl, aralkyl, and hetero; and Z is hydroxy, amino, alkylamino, dialkylamino, or alkoxy; and non-toxic pharmaceutically-acceptable salts of the said compounds.

  本发明涉及具有宝贵药物活性的新化合物。它特别涉及具有抗高血压和血管紧张素转换酶抑制活性并具有以下结构的化合物： 其中 Q 是氧、硫或 NH； X和Y是氢、卤素、羟基、烷氧基 X和Y是氢、卤素、羟基、烷氧基、三氟甲基、硝基、羧基、氰基、磺酰氨基 巯基、烷基、烯基、炔基、烷酰基、烷基巯基、氨基、烷基氨基、二烷基氨基、 烷基亚磺酰基和烷基磺酰基，可以相同或不同； R，是氢、烷酰基、取代基为羟基、氨基或环烷基、芳基、芳基烷酰基或环烷基羰基的取代烷酰基、 n 为 4（含 4）以下的整数、 R2 和 R3 为氢、烷基、烯基、炔基、环烷基、环烷基-烷基、芳基、芳烷基及其取代衍生物，其中取代基为羟基、氨基、烷基氨基、二烷基氨基、烷氧基、卤素、羟基、巯基、烷基巯基和硝基，可以相同或不同； M 是烷基、烯基、炔基、环烷基、环烷基-烷基、芳基、芳烷基和杂基；Z 是羟基、氨基、烷基氨基、二烷基氨基或烷氧基；以及上述化合物的无毒药学上可接受的盐。
• US4440941A
  申请人：——

  公开号：US4440941A

  公开（公告）日：1984-04-03
• 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.