(3S,6S,10S)-[3-(benzhydrylcarbamoyl)-5-oxooctahydropyrrolo[1,2-a]azepin-6-yl]carbamic acid tert-butyl ester | 920267-47-6

• 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,10S)-[3-(benzhydrylcarbamoyl)-5-oxooctahydropyrrolo[1,2-a]azepin-6-yl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S,6S,9aS)-3-(benzhydrylcarbamoyl)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]carbamate
• CAS: 920267-47-6
• 化学式: C₂₈H₃₅N₃O₄
• 分子量: 477.604
• InChiKey: OXJXZBVFQFHGCY-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,6S,10S)-[3-(benzhydrylcarbamoyl)-5-oxooctahydropyrrolo[1,2-a]azepin-6-yl]carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Potent, Cell-Permeable, Conformationally Constrained Second Mitochondria Derived Activator of Caspase (Smac) Mimetic

  摘要：

  A potent, cell-permeable, conformationally constrained second mitochondria derived activator of caspase mimetic (SM-131, 2) has been designed, synthesized, and evaluated. Compound 2 binds to X-linked inhibitors of apoptosis proteins (XIAP) with a K-i of 61 nM in a competitive binding assay and directly antagonizes the XIAP inhibition of caspase-9 activity in a cell-free functional assay. Compound 2 achieves an IC50 of 100 nM in inhibition of cell growth and effectively induces cell death in the MDA-MB-231 human breast cancer cell line.

  DOI：

  10.1021/jm061108d
• 作为产物：
  描述：

  (3S,6S,9aS)-6-((tert-Butoxycarbonyl)amino)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid 、 二苯甲胺 在 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92%的产率得到(3S,6S,10S)-[3-(benzhydrylcarbamoyl)-5-oxooctahydropyrrolo[1,2-a]azepin-6-yl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Potent, Cell-Permeable, Conformationally Constrained Second Mitochondria Derived Activator of Caspase (Smac) Mimetic

  摘要：

  A potent, cell-permeable, conformationally constrained second mitochondria derived activator of caspase mimetic (SM-131, 2) has been designed, synthesized, and evaluated. Compound 2 binds to X-linked inhibitors of apoptosis proteins (XIAP) with a K-i of 61 nM in a competitive binding assay and directly antagonizes the XIAP inhibition of caspase-9 activity in a cell-free functional assay. Compound 2 achieves an IC50 of 100 nM in inhibition of cell growth and effectively induces cell death in the MDA-MB-231 human breast cancer cell line.

  DOI：

  10.1021/jm061108d

文献信息

• Design, Synthesis, and Evaluation of a Potent, Cell-Permeable, Conformationally Constrained Second Mitochondria Derived Activator of Caspase (Smac) Mimetic
  作者：Haiying Sun、Zaneta Nikolovska-Coleska、Jianfeng Lu、Su Qiu、Chao-Yie Yang、Wei Gao、Jennifer Meagher、Jeanne Stuckey、Shaomeng Wang

  DOI：10.1021/jm061108d

  日期：2006.12.1

  A potent, cell-permeable, conformationally constrained second mitochondria derived activator of caspase mimetic (SM-131, 2) has been designed, synthesized, and evaluated. Compound 2 binds to X-linked inhibitors of apoptosis proteins (XIAP) with a K-i of 61 nM in a competitive binding assay and directly antagonizes the XIAP inhibition of caspase-9 activity in a cell-free functional assay. Compound 2 achieves an IC50 of 100 nM in inhibition of cell growth and effectively induces cell death in the MDA-MB-231 human breast cancer cell line.