(3S,6S)-6-phthalimido-3-(2-thienyl)perhydro-1,4-thiazepin-5-one | 110221-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3S,6S)-6-phthalimido-3-(2-thienyl)perhydro-1,4-thiazepin-5-one
• 英文别名: 2-[(3S,6S)-5-oxo-3-thiophen-2-yl-1,4-thiazepan-6-yl]isoindole-1,3-dione
• CAS: 110221-61-9
• 化学式: C₁₇H₁₄N₂O₃S₂
• 分子量: 358.442
• InChiKey: AIULRAOXNRZXRU-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S)-3-[(2S)-2-amino-2-thiophen-2-ylethyl]sulfanyl-2-(1,3-dioxoisoindol-2-yl)propanoic acid;2,2,2-trifluoroacetic acid 、 N-甲基吗啉 以46%的产率得到
  参考文献：
  名称：

  YANAGISAWA, HIROAKI;ISHIHARA, SADAO;ANDO, AKIKO;KANAZAKI, TAKURO;MIYAMOTO+, J. MED. CHEM., 30,(1987) N 11, 1984-1991

  摘要：

  DOI：

文献信息

• Angiotensin-converting enzyme inhibitors. Perhydro-1,4-thiazepin-5-one derivatives
  作者：Hiroaki Yanagisawa、Sadao Ishihara、Akiko Ando、Takuro Kanazaki、Shuichi Miyamoto、Hiroyuki Koike、Yasuteru Iijima、Kiyoshi Oizumi、Yoichi Matsushita、Tadashi Hata

  DOI：10.1021/jm00394a009

  日期：1987.11

  alpha-[6-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-5-oxoperhydro -1,4-thiazepin-4-yl]acetic acids (monoester monoacids) and their dicarboxylic acids having the hydrophobic substituents at the 2- or 3-position of the thiazepinone ring were prepared and assayed for angiotensin-converting enzyme (ACE) inhibitory activity. The dicarboxylic acids having the pseudoequatorial amino groups at the 6-position and the pseudoequatorial hydrophobic substituents at the 2- or 3-position of the chair conformation of the thiazepinone ring had potent in vitro inhibitory activity. The monoester monoacids having the hydrophobic substituents at the 2-position suppressed pressor response to angiotensin I for a longer duration than those having the substituents at the 3-position when administered orally. The structure-activity relationship was studied by conformational energy calculations of the thiazepinone ring.