1-ethyl 2-methyl 3,4-dihydro-1H-pyrido[3,4-b]indole-1,2(9H)-dicarboxylate | 1396178-66-7

• 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: 1-ethyl 2-methyl 3,4-dihydro-1H-pyrido[3,4-b]indole-1,2(9H)-dicarboxylate
• 英文别名: 1-O-ethyl 2-O-methyl 1,3,4,9-tetrahydropyrido[3,4-b]indole-1,2-dicarboxylate
• CAS: 1396178-66-7
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: OKGYUYKOENCFFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethyl 2-methyl 3,4-dihydro-1H-pyrido[3,4-b]indole-1,2(9H)-dicarboxylate 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以66%的产率得到1-ethyl 2-methyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-1,2(9H)-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
• 作为产物：
  描述：

  色胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 生成 1-ethyl 2-methyl 3,4-dihydro-1H-pyrido[3,4-b]indole-1,2(9H)-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