3-[4-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester | 447408-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[4-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-2,5-dioxo-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-[4-[1-(benzenesulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-1-methyl-2,5-dioxopyrrol-3-yl]pyrrolo[2,3-b]pyridine-1-carboxylate
• CAS: 447408-29-9
• 化学式: C₃₀H₂₅N₅O₆S
• 分子量: 583.624
• InChiKey: SLGVCHTXQLLDME-UHFFFAOYSA-N

物化性质

• 沸点：
  803.0±75.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[4-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到1-methyl-3,4-bis(1H-pyrrolo[2,3-b]pyridin-3-yl)-pyrrole-2,5-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 在 4-二甲氨基吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 17.0h， 生成 3-[4-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridine-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

• First synthesis of symmetrical and non-symmetrical aza indolocarbazoles derivatives
  作者：Sylvain Routier、Gérard Coudert、Jean-Yves Mérour、Daniel Henri Caignard

  DOI：10.1016/s0040-4039(02)00315-5

  日期：2002.4

  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.