4(S)-(2(S)-acetylamino-3-phenyl-propionylamino)-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid hydroxyamide

• 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: 4(S)-(2(S)-acetylamino-3-phenyl-propionylamino)-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid hydroxyamide
• 英文别名: (2S,3S,4S,5R)-4-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-N-hydroxy-5-(2-methoxyethoxy)-3-(2-methylpropyl)oxolane-2-carboxamide
• 化学式: C₂₃H₃₅N₃O₇
• 分子量: 465.547
• InChiKey: LXCRKXCDSKGGDS-GZMKSWLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 在 N-甲基吗啉 、 sodium chlorite 、 sodium dihydrogenphosphate 、 四丙基高钌酸铵 、 2-甲基-2-丁烯 、 4 A molecular sieve 、 四丁基氟化铵 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 19.0h， 生成 4(S)-(2(S)-acetylamino-3-phenyl-propionylamino)-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Tetrahydrofuran as a Scaffold for Peptidomimetics. Application to the Design and Synthesis of Conformationally Constrained Metalloproteinase Inhibitors

  摘要：

  Enantiopure functionalized tetrahydrofurans were synthesized as prototypical conformationally constrained analogs of acyclic succinic acid-based inhibitors of metalloproteinases. While preliminary docking study showed good congruence with a potent inhibitor, the biological results were disappointing. Molecular dynamics simulation revealed the weakness of the H-bond interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00687-6

文献信息

• Tetrahydrofuran as a Scaffold for Peptidomimetics. Application to the Design and Synthesis of Conformationally Constrained Metalloproteinase Inhibitors
  作者：Stephen Hanessian、Nicolas Moitessier、Serge Wilmouth

  DOI：10.1016/s0040-4020(00)00687-6

  日期：2000.9

  Enantiopure functionalized tetrahydrofurans were synthesized as prototypical conformationally constrained analogs of acyclic succinic acid-based inhibitors of metalloproteinases. While preliminary docking study showed good congruence with a potent inhibitor, the biological results were disappointing. Molecular dynamics simulation revealed the weakness of the H-bond interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.