tert-butyl α-<(3S^*,6R^*)-3-azido-2-oxo-6-phenylperhydroazepin-1-yl>acetate | 111743-03-4

• 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: tert-butyl α-<(3S^*,6R^*)-3-azido-2-oxo-6-phenylperhydroazepin-1-yl>acetate
• 英文别名: t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate；tert-butyl 2-[(3R,6S)-3-azido-2-oxo-6-phenylazepan-1-yl]acetate
• CAS: 111743-03-4
• 化学式: C₁₈H₂₄N₄O₃
• 分子量: 344.414
• InChiKey: PAISPYBAMGGCGB-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl α-<(3S^*,6R^*)-3-azido-2-oxo-6-phenylperhydroazepin-1-yl>acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 tert-butyl α-<(3S^*,6R^*)-3-amino-2-oxo-6-phenylperhydroazepin-1-yl>acetate
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives

  摘要：

  alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.

  DOI：

  10.1021/jm00397a027
• 作为产物：
  描述：

  ethyl 6-amino-5-phenylhexanoate 在 盐酸 、 sodium hydroxide 、 sodium azide 、 五氯化磷 、 溴 、 碘 、 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 10.0h， 生成 tert-butyl α-<(3S^*,6R^*)-3-azido-2-oxo-6-phenylperhydroazepin-1-yl>acetate
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives

  摘要：

  alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.

  DOI：

  10.1021/jm00397a027

文献信息

• Lactam derivatives and their use as hypotensive agents
  申请人：Sankyo Company Limited

  公开号：US04734410A1

  公开（公告）日：1988-03-29

  Compounds of formula (I): ##STR1## (wherein R.sup.1 and R.sup.3 are organic groups, A is a direct bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CO--CH.sub.2, --O--CH.sub.2 -- or --S--CH.sub.2 --, B is lower alkylene and n is 1-3) are valuable hypotensive agents which may be prepared by a condensation reaction of the corresponding compound having an amino group at the 3-position.

  化合物的式子为(I): ##STR1## (其中R.sup.1和R.sup.3为有机基团，A是直接键，--CH.sub.2 --，--CH.sub.2 CH.sub.2 --，--CO--CH.sub.2，--O--CH.sub.2 --或--S--CH.sub.2 --，B是低碳链烷基，n为1-3)是有价值的降压剂，可以通过相应化合物在3位具有氨基的缩合反应制备。
• YANAGISAWA, HIROAKI;ISHIHARA, SADAO;ANDO, AKIKO;KANAZAKI, TAKURO;MIYAMOTO+, J. MED. CHEM., 31,(1988) N 2, 422-428
  作者：YANAGISAWA, HIROAKI、ISHIHARA, SADAO、ANDO, AKIKO、KANAZAKI, TAKURO、MIYAMOTO+

  DOI：——

  日期：——
• Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-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/jm00397a027

  日期：1988.2

  alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.