1-carboxymethyl-3-[1-carboxy-2-phenylthio-(1R)-ethylamino]-2,3,4,5-tetrahydro-1H-[1]-3S-benzazepin-2-one | 95384-24-0

• 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: 1-carboxymethyl-3-[1-carboxy-2-phenylthio-(1R)-ethylamino]-2,3,4,5-tetrahydro-1H-[1]-3S-benzazepin-2-one
• 英文别名: 2-(1-Carboxymethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-3-phenylsulfanyl-propionic acid；(2R)-2-[[(3S)-1-(carboxymethyl)-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl]amino]-3-phenylsulfanylpropanoic acid
• CAS: 95384-24-0
• 化学式: C₂₁H₂₂N₂O₅S
• 分子量: 414.482
• InChiKey: ZXTSTZUERUGEPU-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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 1-carboxymethyl-3-[1-carboxy-2-phenylthio-(1R)-ethylamino]-2,3,4,5-tetrahydro-1H-[1]-3S-benzazepin-2-one
  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

• 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.