(1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester | 667468-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester
• 英文别名: 2-O-benzyl 3-O-ethyl (3S,3aS,6R,6aR)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2,3-dicarboxylate
• CAS: 667468-11-3
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: QAWXMUWTWFMRRF-JONQDZQNSA-N

物化性质

• 沸点：
  476.0±45.0 °C(predicted)
• 密度：
  1.265±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(1S,3aR,4S,6aS)-4-Fluoro-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl 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,6as)-1-乙基-2-(苯基甲基)酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester 、 (1S,3aR,4S,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl 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

文献信息

• Discovery of a novel bicycloproline P2 bearing peptidyl α-ketoamide LY514962 as HCV protease inhibitor
  作者：Yvonne Yip、Frantz Victor、Jason Lamar、Robert Johnson、Q.May Wang、Donna Barket、John Glass、Ling Jin、Lifei Liu、Daryl Venable、Mark Wakulchik、Congping Xie、Beverly Heinz、Elcira Villarreal、Joe Colacino、Nathan Yumibe、Mark Tebbe、John Munroe、Shu-Hui Chen

  DOI：10.1016/j.bmcl.2003.09.074

  日期：2004.1

  We describe herein the design, syntheses and evaluation of a number of bicycloproline P2 bearing HCV protease inhibitors endowed with impressive enzyme potency, enzyme selectivity, cellular activity and favorable ADME profiles. (C) 2003 Elsevier Ltd. All rights reserved.
• Peptidomimetic protease inhibitors and intermediates for their preparation As treatment for HCV infection
  申请人：Vertex Pharmaceuticals Inc.

  公开号：EP2368877B1

  公开（公告）日：2014-05-07
• US7820671B2
  申请人：——

  公开号：US7820671B2

  公开（公告）日：2010-10-26