di-tert-butyl 1-(1-(1,3-dimethyl-2,4,6-trioxo-hexahydropyrimidin-5-yl)propan-2-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate | 1396178-56-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: di-tert-butyl 1-(1-(1,3-dimethyl-2,4,6-trioxo-hexahydropyrimidin-5-yl)propan-2-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate
• 英文别名: ditert-butyl 1-[1-(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)propan-2-yl]-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate
• CAS: 1396178-56-5
• 化学式: C₃₀H₄₀N₄O₇
• 分子量: 568.67
• InChiKey: WNKFTTYVPDBKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 1-(1-(1,3-dimethyl-2,4,6-trioxo-hexahydropyrimidin-5-yl)propan-2-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 以98%的产率得到tert-butyl 1-(1-(1,3-dimethyl-2,4,6-trioxo-hexahydropyrimidin-5-yl)propan-2-yl)-1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carboxylate
  参考文献：
  名称：

  Design and synthesis of Pictet–Spengler condensation products that exhibit oncogenic-RAS synthetic lethality and induce non-apoptotic cell death

  摘要：

  A series of Pictet-Spengler condensation derivatives (tetrahydro-beta-carbolines) was designed, synthesized and evaluated for lethality against a panel of seven cancer cell lines. Seven compounds (2a, 13, 20, 21, 27, 29 and 34) showed lethality in at least five cell lines. Among these, compound 27 showed a unique selectivity towards oncogenic-RAS expressing BJ-TERT/LT/ST/RAS(V12) tumor cells, compared to non-transformed BJ-TERT cells. Further investigation revealed that 27 induces cell death without activation of caspases. This represents a useful new probe of non-apoptotic cell death and oncogenic-RAS synthetic lethality. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.077
• 作为产物：
  描述：

  ethyl 2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)propanoate 在 4-二甲氨基吡啶 、 二氢吡啶 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 L-脯氨酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 56.0h， 生成 di-tert-butyl 1-(1-(1,3-dimethyl-2,4,6-trioxo-hexahydropyrimidin-5-yl)propan-2-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate
  参考文献：
  名称：

  Design and synthesis of Pictet–Spengler condensation products that exhibit oncogenic-RAS synthetic lethality and induce non-apoptotic cell death

  摘要：

  A series of Pictet-Spengler condensation derivatives (tetrahydro-beta-carbolines) was designed, synthesized and evaluated for lethality against a panel of seven cancer cell lines. Seven compounds (2a, 13, 20, 21, 27, 29 and 34) showed lethality in at least five cell lines. Among these, compound 27 showed a unique selectivity towards oncogenic-RAS expressing BJ-TERT/LT/ST/RAS(V12) tumor cells, compared to non-transformed BJ-TERT cells. Further investigation revealed that 27 induces cell death without activation of caspases. This represents a useful new probe of non-apoptotic cell death and oncogenic-RAS synthetic lethality. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.077