[(S)-1-((1S,3aR,4S,6aS)-4-Fluoro-1-{1-[hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butylcarbamoyl}-hexahydro-cyclopenta[c]pyrrole-2-carbonyl)-2-methyl-propyl]-carbamic acid isopropyl ester | 628729-10-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: [(S)-1-((1S,3aR,4S,6aS)-4-Fluoro-1-{1-[hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butylcarbamoyl}-hexahydro-cyclopenta[c]pyrrole-2-carbonyl)-2-methyl-propyl]-carbamic acid isopropyl ester
• CAS: 628729-10-2
• 化学式: C₃₁H₄₇FN₄O₆
• 分子量: 590.736
• InChiKey: KZWZOCPDTKMMKK-WHPSSRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  137.07
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-((1S,3aR,4S,6aS)-4-Fluoro-1-{1-[hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butylcarbamoyl}-hexahydro-cyclopenta[c]pyrrole-2-carbonyl)-2-methyl-propyl]-carbamic acid isopropyl ester 在 戴斯-马丁氧化剂 作用下， 以90%的产率得到((S)-1-{(1S,3aR,4S,6aS)-4-Fluoro-1-[1-((S)-1-phenyl-ethylaminooxalyl)-butylcarbamoyl]-hexahydro-cyclopenta[c]pyrrole-2-carbonyl}-2-methyl-propyl)-carbamic acid isopropyl ester
  参考文献：
  名称：

  Synthesis and evaluation of tripeptidyl α-Ketoamides as human rhinovirus 3C protease inhibitors

  摘要：

  We describe herein the synthesis and biological evaluation of a series of tripeptidyl alpha-ketoamides as human rhinovirus (HRV) 3C protease inhibitors. The most potent inhibitor discussed in this manuscript, 41, exhibited impressive enzyme inhibitory activity as well as antiviral activity against HRV-14. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00753-4
• 作为产物：
  描述：

  (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester 在 palladium dihydroxide sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 [(S)-1-((1S,3aR,4S,6aS)-4-Fluoro-1-{1-[hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butylcarbamoyl}-hexahydro-cyclopenta[c]pyrrole-2-carbonyl)-2-methyl-propyl]-carbamic acid isopropyl ester
  参考文献：
  名称：

  Synthesis and evaluation of tripeptidyl α-Ketoamides as human rhinovirus 3C protease inhibitors

  摘要：

  We describe herein the synthesis and biological evaluation of a series of tripeptidyl alpha-ketoamides as human rhinovirus (HRV) 3C protease inhibitors. The most potent inhibitor discussed in this manuscript, 41, exhibited impressive enzyme inhibitory activity as well as antiviral activity against HRV-14. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00753-4