3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester | 447408-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-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]pyrrolo[2,3-b]pyridine-1-carboxylate
• CAS: 447408-31-3
• 化学式: C₂₄H₂₁N₅O₄
• 分子量: 443.462
• InChiKey: NOZRSQUWCROJGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester 在 碘 作用下， 以 苯 为溶剂， 反应 3.5h， 以74%的产率得到6-methyl-13H-pyrido[2,3-b]pyrrolo[3,4-e]pyrido[3',2':4,5]pyrrolo[3,2-g]indole-5,7-dione-12-carboxylic acid tert-butylester
  参考文献：
  名称：

  First synthesis of symmetrical and non-symmetrical aza indolocarbazoles derivatives

  摘要：

  A new family of aza-indolocarbazoles 2-3 was built from protected 3-(3-indolyl)-4-bromo-N-methylmaleimide in a few efficient steps. Symmetrical and non-symmetrical products were obtained. Regioselectivity of anionic condensation was controlled. A possible selective deprotection between an N-Boc and N-benzenesulphonyl group using mild basic conditions was confirmed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00315-5
• 作为产物：
  描述：

  7-氮杂吲哚 在 4-二甲氨基吡啶 、 乙基溴化镁 、 四丁基氟化铵 、 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.0h， 生成 3-[1-methyl-2,5-dioxo-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  First synthesis of symmetrical and non-symmetrical aza indolocarbazoles derivatives

  摘要：

  A new family of aza-indolocarbazoles 2-3 was built from protected 3-(3-indolyl)-4-bromo-N-methylmaleimide in a few efficient steps. Symmetrical and non-symmetrical products were obtained. Regioselectivity of anionic condensation was controlled. A possible selective deprotection between an N-Boc and N-benzenesulphonyl group using mild basic conditions was confirmed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00315-5

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.