(3R)-4-[2-(3-chlorophenyl)pyrrolidin-1-yl]-3-hydroxy-4-oxo-N-(2-thiophen-2-ylethyl)butanamide | 1218950-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R)-4-[2-(3-chlorophenyl)pyrrolidin-1-yl]-3-hydroxy-4-oxo-N-(2-thiophen-2-ylethyl)butanamide
• CAS: 1218950-22-1
• 化学式: C₂₀H₂₃ClN₂O₃S
• 分子量: 406.933
• InChiKey: JXKKCEXDWZYEOX-QRWMCTBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(3-氯苯基)吡咯烷 、 (R)-2-hydroxy-4-oxo-4-((2-(thiophen-2-yl)ethyl)amino)butanoic acid 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到(3R)-4-[2-(3-chlorophenyl)pyrrolidin-1-yl]-3-hydroxy-4-oxo-N-(2-thiophen-2-ylethyl)butanamide
  参考文献：
  名称：

  The discovery of novel tartrate-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A novel series of TNF-alpha convertase (TACE) inhibitors which are non-hydroxamate have been discovered. These compounds are bis-amides of L-tartaric acid (tartrate) and coordinate to the active site zinc in a tridentate manner. They are selective for TACE over other MMP's. We report the first X-ray crystal structure for a tartrate-based TACE inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.004

文献信息

• The discovery of novel tartrate-based TNF-α converting enzyme (TACE) inhibitors
  作者：Kristin E. Rosner、Zhuyan Guo、Peter Orth、Gerald W. Shipps、David B. Belanger、Tin Yau Chan、Patrick J. Curran、Chaoyang Dai、Yongqi Deng、Vinay M. Girijavallabhan、Liwu Hong、Brian J. Lavey、Joe F. Lee、Dansu Li、Zhidan Liu、Janeta Popovici-Muller、Pauline C. Ting、Henry Vaccaro、Li Wang、Tong Wang、Wensheng Yu、Guowei Zhou、Xiaoda Niu、Jing Sun、Joseph A. Kozlowski、Daniel J. Lundell、Vincent Madison、Brian McKittrick、John J. Piwinski、Neng -Yang Shih、M. Arshad Siddiqui、Corey O. Strickland

  DOI：10.1016/j.bmcl.2009.12.004

  日期：2010.2

  A novel series of TNF-alpha convertase (TACE) inhibitors which are non-hydroxamate have been discovered. These compounds are bis-amides of L-tartaric acid (tartrate) and coordinate to the active site zinc in a tridentate manner. They are selective for TACE over other MMP's. We report the first X-ray crystal structure for a tartrate-based TACE inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.