N-<(cyclopent-2-enyl)acetyl>valine methyl ester | 173680-62-1

• 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-<(cyclopent-2-enyl)acetyl>valine methyl ester
• 英文别名: methyl (2S)-2-[(2-cyclopent-2-en-1-ylacetyl)amino]-3-methylbutanoate
• CAS: 173680-62-1
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: RXZGNSAGZCUWBK-KFJBMODSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<(cyclopent-2-enyl)acetyl>valine methyl ester 在 palladium on activated charcoal sodium azide 、 氢气 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 64.0h， 生成
  参考文献：
  名称：

  Progress towards new conformationally constrained HIV-1 protease inhibitors

  摘要：

  Two series of molecules containing a trisubstituted cyclopentyl group as the central unit were synthesized and evaluated as inhibitors of HIV-1 protease (HIV PR). In the first series of molecules (13-20), the central unit A, 3-(N-acyl)amino-2-hydroxy-1-cyclopentylacetyl, was designed so as to reproduce three of the central interactions found in the 'classical' complex HIV PR-JG365 inhibitor. Significant inhibitions (IC50 similar to 10 mu M) were obtained with compound 20 in which the central unit was elongated by Z-Ile-Phe at the N-terminus and by Val-OMe at the C-terminus. In the second series of molecules (21-28), the central unit B, 3-hydroxy-2-(N-acyl)amino-1-cyclopentylacetyl, was obtained in the first steps of the synthesis. Unexpectedly better inhibitions were observed with these derivatives (K-i = 2 mu M for compound 28). Docking and molecular dynamics simulations performed with compound 28 into HIV PR suggested that the HIV PR-28 complex should have a structure analogous to that of the recently described HIV PR-urea complex.

  DOI：

  10.1016/0223-5234(96)88308-5
• 作为产物：
  描述：

  2-环戊烯基-1-乙酸 、 L-缬氨酸甲酯盐酸盐 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 生成 N-<(cyclopent-2-enyl)acetyl>valine methyl ester
  参考文献：
  名称：

  Progress towards new conformationally constrained HIV-1 protease inhibitors

  摘要：

  Two series of molecules containing a trisubstituted cyclopentyl group as the central unit were synthesized and evaluated as inhibitors of HIV-1 protease (HIV PR). In the first series of molecules (13-20), the central unit A, 3-(N-acyl)amino-2-hydroxy-1-cyclopentylacetyl, was designed so as to reproduce three of the central interactions found in the 'classical' complex HIV PR-JG365 inhibitor. Significant inhibitions (IC50 similar to 10 mu M) were obtained with compound 20 in which the central unit was elongated by Z-Ile-Phe at the N-terminus and by Val-OMe at the C-terminus. In the second series of molecules (21-28), the central unit B, 3-hydroxy-2-(N-acyl)amino-1-cyclopentylacetyl, was obtained in the first steps of the synthesis. Unexpectedly better inhibitions were observed with these derivatives (K-i = 2 mu M for compound 28). Docking and molecular dynamics simulations performed with compound 28 into HIV PR suggested that the HIV PR-28 complex should have a structure analogous to that of the recently described HIV PR-urea complex.

  DOI：

  10.1016/0223-5234(96)88308-5