tert-butyl 5-(benzyloxy)-3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate | 494747-92-1

• 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: tert-butyl 5-(benzyloxy)-3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate
• 英文别名: Tert-butyl 3-(4-bromo-1-methyl-2,5-dioxopyrrol-3-yl)-5-phenylmethoxyindole-1-carboxylate
• CAS: 494747-92-1
• 化学式: C₂₅H₂₃BrN₂O₅
• 分子量: 511.372
• InChiKey: MDOFBGXZKYSUAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-(benzyloxy)-3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate 在 四丁基氟化铵 、 碘 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 3.83h， 生成 6-methyl-9-benzyloxy-12,13-dihydropyrrolo[2,3-a]pyrrolo[3,4-c]pyrido[3',2':4,5]carbazole-5,7-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 7-azaindolocarbazoles

  摘要：

  In the course of a program aimed at designing antitumor agents containing an indolocarbazole framework, an efficient synthetic scheme based on the use of 3,4-dibromo-N-methylmaleimide and 7-azaindole has been developed to elaborate a series of mono- and di-aza derivatives of arcyriaflavin. The procedure was further exploited to introduce a hydroxyl group at different positions on the indole moiety of the non-symmetrical compounds. The DNA binding capacity and cytotoxic potential of these 7-azaindolocarbazole derivatives was evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00691-9

文献信息

• Synthesis and biological evaluation of novel benzodioxinocarbazoles (BDCZs) as potential anticancer agents
  作者：Nathalie Ayerbe、Sylvain Routier、Isabelle Gillaizeau、Carmen Maiereanu、Daniel-Henry Caignard、Alain Pierré、Stéphane Léonce、Gérard Coudert

  DOI：10.1016/j.bmcl.2010.05.088

  日期：2010.8

  We report the efficient synthesis and biological evaluation of new benzodioxinoindolocarbazoles heterocycles (BDCZs) designed as potential anticancer agents. Indolic substitution and maleimide variations were performed to design a new library of BDCZs and their cytotoxicity were evaluated on two representative cancer cell lines. Several derivatives have shown a marked cytotoxicity with IC50 values in the nanomolar range. Results are reported in this Letter. (C) 2010 Elsevier Ltd. All rights reserved.