(2S)-N-(diphenylmethyl)-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidine-2-carboxamide;methanoic acid | 1186656-79-0

• 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: (2S)-N-(diphenylmethyl)-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidine-2-carboxamide;methanoic acid
• 英文别名: (2S)-N-benzhydryl-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidine-2-carboxamide
• CAS: 1186656-79-0
• 化学式: C₂₆H₃₄N₄O₃
• 分子量: 450.581
• InChiKey: QJFREKIHMCIWKO-NYVOZVTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-脯氨酸苄酯 在 N-甲基吗啉 、 palladium on carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-N-(diphenylmethyl)-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidine-2-carboxamide;methanoic acid
  参考文献：
  名称：

  Design, synthesis and evaluation of monovalent Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP

  摘要：

  We report the systematic rational design and synthesis of new monovalent Smac mimetics that bind preferentially to the BIR2 domain of the anti-apoptotic protein XIAP. Characterization of compounds in vitro (including 9i; ML101) led to the determination of key structural requirements for BIR2 binding affinity. Compounds 9h and 9j sensitized TRAIL-resistant breast cancer cells to apoptotic cell death, highlighting the value of these probe compounds as tools to investigate the biology of XIAP. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.049

文献信息

• Small molecule apoptosis promoters
  申请人：Hanson J. Gunnar

  公开号：US20080051389A1

  公开（公告）日：2008-02-28

  The invention provides small molecule mimics of the Smac peptide that are dimer- or dimer-like compounds having two amide-containing domains connected by a linker. These compounds are useful to promote apoptosis. The invention includes pharmaceutical compositions comprising such compounds and methods to use them to treat conditions including cancer and autoimmune disorders.

  本发明提供了Smac肽的小分子模拟物，这些模拟物是由两个含有酰胺结构域的化合物连接而成的二聚体或类二聚体化合物。这些化合物可用于促进细胞凋亡。本发明还包括包含这些化合物的制药组合物以及使用它们治疗包括癌症和自身免疫性疾病在内的疾病的方法。
• US7807699B2
  申请人：——

  公开号：US7807699B2

  公开（公告）日：2010-10-05
• Design, synthesis and evaluation of monovalent Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP
  作者：Marcos González-Lόpez、Kate Welsh、Darren Finlay、Robert J. Ardecky、Santhi Reddy Ganji、Ying Su、Hongbin yuan、Peter Teriete、Peter D. Mace、Stefan J. Riedl、Kristiina Vuori、John C. Reed、Nicholas D.P. Cosford

  DOI：10.1016/j.bmcl.2011.05.049

  日期：2011.7

  We report the systematic rational design and synthesis of new monovalent Smac mimetics that bind preferentially to the BIR2 domain of the anti-apoptotic protein XIAP. Characterization of compounds in vitro (including 9i; ML101) led to the determination of key structural requirements for BIR2 binding affinity. Compounds 9h and 9j sensitized TRAIL-resistant breast cancer cells to apoptotic cell death, highlighting the value of these probe compounds as tools to investigate the biology of XIAP. (C) 2011 Elsevier Ltd. All rights reserved.