benzyl (3S,6S,10aR)-8-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxylate | 957136-22-0

• 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: benzyl (3S,6S,10aR)-8-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxylate
• CAS: 957136-22-0
• 化学式: C₂₃H₃₂N₂O₆
• 分子量: 432.517
• InChiKey: WCLNEGQNIRUOME-RNLLHNEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  benzyl (3S,6S,10aR)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-2,3,6,7,10,10a-hexahydro-1H-pyrrolo[1,2-a]azocine-3-carboxylate 在 9λ²-borabicyclo[3.3.1]nonane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以25%的产率得到benzyl (3S,6S,9R,10aR)-6-(tert-butoxycarbonylamino)-9-hydroxy-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxylate
  参考文献：
  名称：

  Nonpeptidic and Potent Small-Molecule Inhibitors of cIAP-1/2 and XIAP Proteins

  摘要：

  A series of compounds were designed and synthesized as antagonists of cIAP-1/2 and XIAP based upon our previously identified lead compound SM-122 (1). The most potent of these (7) binds to XIAP, cIAP-1, and cIAP-2 proteins with K(i) values of 36, <1, and <1.9 nM, respectively. Consistent with its potent binding affinities to IAPs, 7 effectively antagonizes XIAP in a cell-free caspase-9 functional assay, efficiently induces cIAP-1 degradation in cells at concentrations as low as 10 nM, and triggers activation of caspases and PARP cleavage in the MDA-MB-231 breast cancer cell line. Compound 7 potently inhibits cell growth in the MDA-MB-231 cancer cell line with an IC(50) value of 200 nM and is 9 times more potent than compound 1.

  DOI：

  10.1021/jm100487z