methyl (3S,6S,11bR)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoyl]amino]-5-oxo-1,2,3,6,7,11b-hexahydropyrrolo[2,1-a][2]benzazepine-3-carboxylate | 1092575-92-2

• 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: methyl (3S,6S,11bR)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoyl]amino]-5-oxo-1,2,3,6,7,11b-hexahydropyrrolo[2,1-a][2]benzazepine-3-carboxylate
• CAS: 1092575-92-2
• 化学式: C₂₄H₃₃N₃O₆
• 分子量: 459.543
• InChiKey: YRGSLJBBEWSIMM-FZDIXFNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3S,6S,11bR)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoyl]amino]-5-oxo-1,2,3,6,7,11b-hexahydropyrrolo[2,1-a][2]benzazepine-3-carboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Tricyclic, Conformationally Constrained Small-Molecule Mimetics of Second Mitochondria-Derived Activator of Caspases

  摘要：

  A series of tricyclic, conformationally constrained Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 6 (WS-5) binds to XIAP, cIAP-1, and cIAP-2 with K-i of 18, 1.1, and 4.2 nM, respectively. Compound 6 antagonizes XIAP in a functional assay, induces cIAP-1 degradation, inhibits cell growth with an IC50 of 68 nM in the MDA-MB-231 cancer cell line, and effectively induces cancer cells to undergo apoptosis.

  DOI：

  10.1021/jm801146d
• 作为产物：
  描述：

  methyl (3S,6S,11bR)-6-amino-5-oxo-1,2,3,6,7,11b-hexahydropyrrolo[2,1-a][2]benzazepine-3-carboxylate 、 BOC-N-甲基-L-丙氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以105 mg的产率得到methyl (3S,6S,11bR)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoyl]amino]-5-oxo-1,2,3,6,7,11b-hexahydropyrrolo[2,1-a][2]benzazepine-3-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Tricyclic, Conformationally Constrained Small-Molecule Mimetics of Second Mitochondria-Derived Activator of Caspases

  摘要：

  A series of tricyclic, conformationally constrained Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 6 (WS-5) binds to XIAP, cIAP-1, and cIAP-2 with K-i of 18, 1.1, and 4.2 nM, respectively. Compound 6 antagonizes XIAP in a functional assay, induces cIAP-1 degradation, inhibits cell growth with an IC50 of 68 nM in the MDA-MB-231 cancer cell line, and effectively induces cancer cells to undergo apoptosis.

  DOI：

  10.1021/jm801146d

文献信息

• Design, Synthesis, and Evaluation of Tricyclic, Conformationally Constrained Small-Molecule Mimetics of Second Mitochondria-Derived Activator of Caspases
  作者：Bin Zhang、Zaneta Nikolovska-Coleska、Yan Zhang、Longchuan Bai、Su Qiu、Chao-Yie Yang、Haiying Sun、Shaomeng Wang、Yikang Wu

  DOI：10.1021/jm801146d

  日期：2008.12.11

  A series of tricyclic, conformationally constrained Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 6 (WS-5) binds to XIAP, cIAP-1, and cIAP-2 with K-i of 18, 1.1, and 4.2 nM, respectively. Compound 6 antagonizes XIAP in a functional assay, induces cIAP-1 degradation, inhibits cell growth with an IC50 of 68 nM in the MDA-MB-231 cancer cell line, and effectively induces cancer cells to undergo apoptosis.