(S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl ester | 847256-22-8

• 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: (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl ester
• CAS: 847256-22-8
• 化学式: C₂₀H₃₅N₃O₆
• 分子量: 413.514
• InChiKey: UKRBQTPKZFBJTR-KKUMJFAQSA-N

物化性质

• 沸点：
  592.5±50.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl ester 在 盐酸 、 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-1-[(S)-2-((S)-2-Amino-butyrylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid benzhydryl-amide; hydrochloride
  参考文献：
  名称：

  Structure-based design, synthesis and biochemical testing of novel and potent Smac peptido-mimetics

  摘要：

  Structure-based design, chemical synthesis and biochemical testing of a series of novel Smac peptido-mimetics as inhibitors of XIAP protein are described. The most potent compound, 6j, has a binding affinity (K-i value) of 24 nM to XIAP BIR3 protein and is 24 times more potent than the native Smac AVPI peptide. Further optimization of these potent Smac mimetics may ultimately lead to the development of a novel class of anticancer drugs for the treatment of human cancer by overcoming apoptosis-resistance of cancer cells through targeting the inhibitor of apoptosis proteins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.008
• 作为产物：
  描述：

  L-脯氨酸甲酯 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure-based design, synthesis and biochemical testing of novel and potent Smac peptido-mimetics

  摘要：

  Structure-based design, chemical synthesis and biochemical testing of a series of novel Smac peptido-mimetics as inhibitors of XIAP protein are described. The most potent compound, 6j, has a binding affinity (K-i value) of 24 nM to XIAP BIR3 protein and is 24 times more potent than the native Smac AVPI peptide. Further optimization of these potent Smac mimetics may ultimately lead to the development of a novel class of anticancer drugs for the treatment of human cancer by overcoming apoptosis-resistance of cancer cells through targeting the inhibitor of apoptosis proteins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.008