5-benzyloxy-3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]indole-1-carboxylic acid tert-butyl ester | 494747-93-2

• 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: 5-benzyloxy-3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]indole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrol-3-yl]-5-phenylmethoxyindole-1-carboxylate
• CAS: 494747-93-2
• 化学式: C₃₂H₂₈N₄O₅
• 分子量: 548.598
• InChiKey: HQLGZFWXBKZBSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]indole-1-carboxylic acid tert-butyl ester 在 四丁基氟化铵 、 碘 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 4.33h， 生成 6-methyl-9-hydroxy-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
• 作为产物：
  描述：

  7-氮杂吲哚 、 tert-butyl 5-(benzyloxy)-3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到5-benzyloxy-3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]indole-1-carboxylic acid tert-butyl ester
  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 7-azaindolocarbazoles
  作者：Sylvain Routier、Nathalie Ayerbe、Jean-Yves Mérour、Gérard Coudert、Christian Bailly、Alain Pierré、Bruno Pfeiffer、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/s0040-4020(02)00691-9

  日期：2002.8

  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.