methyl (4S,7S,12bR)-7-(1,3-dioxoisoindol-2-yl)-6-oxo-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-carboxylate | 116330-65-5

• 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 (4S,7S,12bR)-7-(1,3-dioxoisoindol-2-yl)-6-oxo-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-carboxylate
• CAS: 116330-65-5
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: HRWLEAUQWDVBOA-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 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 (4S,7S,12bR)-7-(1,3-dioxoisoindol-2-yl)-6-oxo-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 methyl (4S,7S,12bR)-7-amino-6-oxo-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-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：

  [S(R*,R*)]-1-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylicacid, methyl ester 在 三氟甲磺酸 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到methyl (4S,7S,12bR)-7-(1,3-dioxoisoindol-2-yl)-6-oxo-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-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

• An acyl-iminium ion cyclization route to a novel conformationally restricted dipeptide mimic: applications to angiotensin-converting enzyme inhibition
  作者：Gary A. Flynn、Eugene L. Giroux、Richard C. Dage

  DOI：10.1021/ja00259a068

  日期：1987.12
• FLYNN, GARY A.;BEIGHT, DOUGLAS W.
  作者：FLYNN, GARY A.、BEIGHT, DOUGLAS W.

  DOI：——

  日期：——