methyl (2S)-1-[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoyl]-2,3-dihydropyrrole-2-carboxylate | 114486-37-2

• 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 (2S)-1-[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoyl]-2,3-dihydropyrrole-2-carboxylate
• CAS: 114486-37-2
• 化学式: C₂₃H₂₀N₂O₅
• 分子量: 404.422
• InChiKey: AVQKDMLSBPPVEJ-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoyl]-2,3-dihydropyrrole-2-carboxylate 在 三氟甲磺酸 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到methyl (3S,6S,11bR)-6-(1,3-dioxoisoindol-2-yl)-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
• 作为产物：
  描述：

  methyl (2S)-2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoyl]amino]-5,5-dimethoxypentanoate 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以88%的产率得到methyl (2S)-1-[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoyl]-2,3-dihydropyrrole-2-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