ditert-butyl 1-[2-(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)ethyl]-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate | 1396178-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ditert-butyl 1-[2-(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)ethyl]-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate
• CAS: 1396178-41-8
• 化学式: C₂₉H₃₈N₄O₇
• 分子量: 554.643
• InChiKey: JPEAYUDTMKXVFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  ditert-butyl 1-[2-(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)ethyl]-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80%的产率得到1,3-dimethyl-5-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)ethyl)pyrimidine-2,4,6(1H,3H,5H)-trione
  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 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二氢吡啶 、 palladium on activated charcoal 、 氢气 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三氟乙酸 、 L-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 89.0h， 生成 ditert-butyl 1-[2-(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)ethyl]-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