3(S)-<<(1R)-2-(benzylthio)-1-carboxyethyl>amino>-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-ethanoic acid | 95384-22-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3(S)-<<(1R)-2-(benzylthio)-1-carboxyethyl>amino>-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-ethanoic acid
• 英文别名: 1-carboxymethyl-3-[1-carboxy-2-benzylthio-(1R)-ethylamino]-2,3,4,5-tetrahydro-1H-[1]-3S-benzazepin-2-one；3(S)-{[(1R)-2-(benzylthio)-1-carboxyethyl]amino}-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-ethanoic acid；3-Benzylsulfanyl-2-(1-carboxymethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-propionic acid；(2R)-3-benzylsulfanyl-2-[[(3S)-1-(carboxymethyl)-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl]amino]propanoic acid
• CAS: 95384-22-8
• 化学式: C₂₂H₂₄N₂O₅S
• 分子量: 428.509
• InChiKey: XCJANLVRPWZEHK-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 3-amino-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one-1-acetate 在 sodium hydroxide 、 亚硝酸特丁酯 、 二丁基二氯化锡 、 sodium cyanoborohydride 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 51.25h， 生成 3(S)-<<(1R)-2-(benzylthio)-1-carboxyethyl>amino>-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-ethanoic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors: structure-activity profile of 1-benzazepin-2-one derivatives

  摘要：

  The preparation of a series of 3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid derivatives 5a-y by reductive amination of 2,3,4,5-tetrahydro-1H-1-benzazepine-2,3-dione (7) with L-amino acid derivatives is described. The compounds were tested for inhibition of angiotensin converting enzyme. The structure-activity profile of the series is discussed. Compound 5a was especially potent when tested in dogs for inhibition of angiotensin I pressor response, having an ID50 = 0.07 mg/kg po.

  DOI：

  10.1021/jm00149a010

文献信息

• 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
  申请人：Ciba-Geigy Corporation

  公开号：US04575503A1

  公开（公告）日：1986-03-11

  Variously substituted 1-carboxymethyl-3-(carboxymethylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin -2-ones and functional derivatives are angiotensin converting enzyme inhibitors and are useful as antihypertensive agents. Synthesis of, compositions and methods of treatment utilizing such compounds are included.

  取代基不同的1-羧甲基-3-(羧甲基氨基)-2,3,4,5-四氢-1H-[1]苯并氮杂䓬-2-酮及其功能性衍生物是血管紧张素转化酶抑制剂，并可作为抗高血压药使用。包括这些化合物的合成、组合物及治疗方法。
• STANTON, J. L.;WATTHEY, J. W. H.;DESAI, M. N.;FINN, B. M.;BABIARZ, J. E.;+, J. MED. CHEM., 1985, 28, N 11, 1603-1606
  作者：STANTON, J. L.、WATTHEY, J. W. H.、DESAI, M. N.、FINN, B. M.、BABIARZ, J. E.、+

  DOI：——

  日期：——
• Gewisse 3-Amino-1-benzazepin-2-on-1-alkansäuren, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0119954B1

  公开（公告）日：1990-03-14
• US4575503A
  申请人：——

  公开号：US4575503A

  公开（公告）日：1986-03-11
• Angiotensin converting enzyme inhibitors: structure-activity profile of 1-benzazepin-2-one derivatives
  作者：James L. Stanton、Jeffrey W. H. Watthey、Mahesh N. Desai、Barbara M. Finn、Joseph E. Babiarz、Hollis C. Tomaselli

  DOI：10.1021/jm00149a010

  日期：1985.11

  The preparation of a series of 3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid derivatives 5a-y by reductive amination of 2,3,4,5-tetrahydro-1H-1-benzazepine-2,3-dione (7) with L-amino acid derivatives is described. The compounds were tested for inhibition of angiotensin converting enzyme. The structure-activity profile of the series is discussed. Compound 5a was especially potent when tested in dogs for inhibition of angiotensin I pressor response, having an ID50 = 0.07 mg/kg po.