N-<(1,1-dimethylethoxy)carbonyl>-4(R)-(4-chlorophenoxy)-(S)-proline | 113507-43-0

• 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: N-<(1,1-dimethylethoxy)carbonyl>-4(R)-(4-chlorophenoxy)-(S)-proline
• 英文别名: (2S,4R)-4-(4-chlorophenoxy)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
• CAS: 113507-43-0
• 化学式: C₁₆H₂₀ClNO₅
• 分子量: 341.791
• InChiKey: XQRJMROGXSIXNT-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-<(1,1-dimethylethoxy)carbonyl>-4(R)-(4-chlorophenoxy)-(S)-proline 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 反应 36.0h， 生成 (2S,4R)-4-(4-Chloro-phenoxy)-1-(3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines

  摘要：

  The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described. These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition. The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril. The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.

  DOI：

  10.1021/jm00399a033
• 作为产物：
  描述：

  1-氯-4-氟苯 、 Boc-L-羟脯氨酸 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以0.65 g的产率得到N-<(1,1-dimethylethoxy)carbonyl>-4(R)-(4-chlorophenoxy)-(S)-proline
  参考文献：
  名称：

  Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines

  摘要：

  The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described. These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition. The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril. The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.

  DOI：

  10.1021/jm00399a033

文献信息

• SMITH, ELIZABETH M.;SWISS, GERALD F.;NEUSTADT, BERNARD R.;GOLD, ELIJAH H.+, J. MED. CHEM., 31,(1988) N 4, 875-885
  作者：SMITH, ELIZABETH M.、SWISS, GERALD F.、NEUSTADT, BERNARD R.、GOLD, ELIJAH H.+

  DOI：——

  日期：——