1-<(tert-butoxycarbonyl)methyl>-3-azidoperhydroazepin-2-one | 99707-44-5

• 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-<(tert-butoxycarbonyl)methyl>-3-azidoperhydroazepin-2-one
• 英文别名: Tert-butyl 2-(3-azido-2-oxoazepan-1-yl)acetate
• CAS: 99707-44-5
• 化学式: C₁₂H₂₀N₄O₃
• 分子量: 268.316
• InChiKey: RCDBGTSKTZSBPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  95.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-<(tert-butoxycarbonyl)methyl>-3-azidoperhydroazepin-2-one 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 生成 (R)-2-((S)-1-Carboxymethyl-2-oxo-azepan-3-ylamino)-4-phenyl-butyric acid ethyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Conformationally restricted inhibitors of angiotensin-converting enzyme. Synthesis and computations

  摘要：

  A series of inhibitors of angiotensin converting enzyme (ACE, dipeptidyl carboxypeptidase, EC 3.4.15.1) is described which addresses certain conformational aspects of the enzyme-inhibitor interaction. In this study the alanylproline portion of the potent ACE inhibitor enalaprilat (2) is replaced by a series of monocyclic lactams containing the required recognition and binding elements. In order to more fully assess the lactam ring conformations and the key backbone angle psi as defined in 3 with respect to possible enzyme-bound conformations, a series of model lactams was investigated with use of molecular mechanics. The results point to a correlation between inhibitor potency (IC50) and the computed psi angle for the lowest energy conformation of the model compounds. Thus the psi angle as defined in 3 is an important determinant in the binding of inhibitors to ACE. The inhibition data in conjunction with the computational data have served to define a window of psi angles from 130 degrees to 170 degrees which seems to be acceptable to the ACE active site.

  DOI：

  10.1021/jm00152a014
• 作为产物：
  描述：

  3-Azidohexahydro-1H-azepin-2-on 、 碘乙酸叔丁酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-<(tert-butoxycarbonyl)methyl>-3-azidoperhydroazepin-2-one
  参考文献：
  名称：

  Conformationally restricted inhibitors of angiotensin-converting enzyme. Synthesis and computations

  摘要：

  A series of inhibitors of angiotensin converting enzyme (ACE, dipeptidyl carboxypeptidase, EC 3.4.15.1) is described which addresses certain conformational aspects of the enzyme-inhibitor interaction. In this study the alanylproline portion of the potent ACE inhibitor enalaprilat (2) is replaced by a series of monocyclic lactams containing the required recognition and binding elements. In order to more fully assess the lactam ring conformations and the key backbone angle psi as defined in 3 with respect to possible enzyme-bound conformations, a series of model lactams was investigated with use of molecular mechanics. The results point to a correlation between inhibitor potency (IC50) and the computed psi angle for the lowest energy conformation of the model compounds. Thus the psi angle as defined in 3 is an important determinant in the binding of inhibitors to ACE. The inhibition data in conjunction with the computational data have served to define a window of psi angles from 130 degrees to 170 degrees which seems to be acceptable to the ACE active site.

  DOI：

  10.1021/jm00152a014