(3S,6S,9aS)-6-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ester | 828295-61-0

• 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: (3S,6S,9aS)-6-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ester
• CAS: 828295-61-0
• 化学式: C₂₀H₃₃N₃O₆
• 分子量: 411.499
• InChiKey: SSRIOFJMXOKYBM-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• 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：

  (3S,6S,9aS)-6-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-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 (3S,6S,9aS)-6-[[(2S)-2-aminobutanoyl]amino]-N-benzhydryl-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxamide;hydrochloride
  参考文献：
  名称：

  Structure-Based Design of Potent, Conformationally Constrained Smac Mimetics

  摘要：

  A successful structure-based design and synthesis of a class of highly potent conformationally constrained Smac mimetics is described. The most potent compound has a Ki value of 25 nM binding to the XIAP BIR3 protein and is 23 times more potent than natural Smac peptides. These potent Smac mimetics can serve as powerful chemical and pharmacological tools to further elucidate the role of Smac and its cellular binding partners in apoptosis regulation and may be developed as a new class of anti-cancer drugs.

  DOI：

  10.1021/ja047438+
• 作为产物：
  描述：

  甲醇 、 BOC-L-2-氨基丁酸 、 (3S,6S,9aS)-tert-butyl 6-(tert-butoxycarbonylamino)-5-oxo-octahydro-1H-pyrrolo [1,2-a]azepine-3-carboxylate 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 二氯甲烷 为溶剂， 以91%的产率得到(3S,6S,9aS)-6-((S)-2-tert-Butoxycarbonylamino-butyrylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure-Based Design of Potent, Conformationally Constrained Smac Mimetics

  摘要：

  A successful structure-based design and synthesis of a class of highly potent conformationally constrained Smac mimetics is described. The most potent compound has a Ki value of 25 nM binding to the XIAP BIR3 protein and is 23 times more potent than natural Smac peptides. These potent Smac mimetics can serve as powerful chemical and pharmacological tools to further elucidate the role of Smac and its cellular binding partners in apoptosis regulation and may be developed as a new class of anti-cancer drugs.

  DOI：

  10.1021/ja047438+