(3S,6S,8AR)-6-((叔丁氧羰基)氨基)-5-氧代八氢吲哚嗪-3-羧酸 | 185121-42-0

• 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
• 中文名称: (3S,6S,8AR)-6-((叔丁氧羰基)氨基)-5-氧代八氢吲哚嗪-3-羧酸
• 英文名称: (3S,6S,8aR)-6-{[(tert-butoxy)carbonyl]amino}-5-oxo-octahydroindolizine-3-carboxylic acid
• 英文别名: (3S,6S,8aR)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylic acid
• CAS: 185121-42-0
• 化学式: C₁₄H₂₂N₂O₅
• 分子量: 298.339
• InChiKey: TUKCETWDNUERKW-UTLUCORTSA-N

物化性质

• 沸点：
  516.2±39.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6S,8AR)-6-((叔丁氧羰基)氨基)-5-氧代八氢吲哚嗪-3-羧酸 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 [(2S)-1-[[(3S,6S,8aR)-3-(benzylcarbamoyl)-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizin-6-yl]amino]-1-oxopropan-2-yl]azanium;chloride
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Evaluation of Conformationally Constrained Mimetics of the Second Mitochondria-Derived Activator of Caspase That Target the X-Linked Inhibitor of Apoptosis Protein/Caspase-9 Interaction Site

  摘要：

  A successful structure-based design of conformationally constrained second mitochondria-derived activator of caspase (Smac) mimetics that target the XIAP/caspase-9 interaction site is described. The most potent Smac mimetic 12d has a K-i of 350 nM for binding to the XIAP BIR3 domain protein. 12d is found to be effective in enhancing apoptosis induced by cisplatin in PC-3 human prostate cancer cells.

  DOI：

  10.1021/jm0499108
• 作为产物：
  描述：

  (3s,6s,8ar)-6-[(叔丁氧基羰基)氨基]-5-氧代八氢吲哚嗪-3-羧酸甲酯 在 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3S,6S,8AR)-6-((叔丁氧羰基)氨基)-5-氧代八氢吲哚嗪-3-羧酸
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Evaluation of Conformationally Constrained Mimetics of the Second Mitochondria-Derived Activator of Caspase That Target the X-Linked Inhibitor of Apoptosis Protein/Caspase-9 Interaction Site

  摘要：

  A successful structure-based design of conformationally constrained second mitochondria-derived activator of caspase (Smac) mimetics that target the XIAP/caspase-9 interaction site is described. The most potent Smac mimetic 12d has a K-i of 350 nM for binding to the XIAP BIR3 domain protein. 12d is found to be effective in enhancing apoptosis induced by cisplatin in PC-3 human prostate cancer cells.

  DOI：

  10.1021/jm0499108

文献信息

• Structure-Based Design, Synthesis, and Evaluation of Conformationally Constrained Mimetics of the Second Mitochondria-Derived Activator of Caspase That Target the X-Linked Inhibitor of Apoptosis Protein/Caspase-9 Interaction Site
  作者：Haiying Sun、Zaneta Nikolovska-Coleska、Chao-Yie Yang、Liang Xu、York Tomita、Krzysztof Krajewski、Peter P. Roller、Shaomeng Wang

  DOI：10.1021/jm0499108

  日期：2004.8.1

  A successful structure-based design of conformationally constrained second mitochondria-derived activator of caspase (Smac) mimetics that target the XIAP/caspase-9 interaction site is described. The most potent Smac mimetic 12d has a K-i of 350 nM for binding to the XIAP BIR3 domain protein. 12d is found to be effective in enhancing apoptosis induced by cisplatin in PC-3 human prostate cancer cells.