12-(6-azido-6-deoxy-4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione | 643064-20-4

• 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: 12-(6-azido-6-deoxy-4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione
• CAS: 643064-20-4
• 化学式: C₂₇H₂₂N₆O₆
• 分子量: 526.508
• InChiKey: VROMGRNEHGVMEY-HHJYCPGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  174.57
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  12-(6-azido-6-deoxy-4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 12-(6-amino-6-deoxy-4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione
  参考文献：
  名称：

  Rebeccamycin analogues bearing amine substituents or other groups on the sugar moiety

  摘要：

  In the course of structure-activity relationship studies on rebeccamycin analogues, a series of compounds bearing an amino function on the sugar moiety were synthesized with the aim of improving the solubility and interaction with the macromolecular target(s). The syntheses of amino derivatives and the corresponding chloro, iodo and azido intermediates are described. Their interaction with DNA and effects on human DNA topoisomerases I and II were investigated. Their antimicrobial activities against two Gram-positive bacteria, Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans were also determined. 6'-Amino compound 7 and 6'-N-methylamino 14 very efficiently inhibit the growth of E. coli. The introduction of an amino group at the 6'-position strongly enhances the capacity of the drugs to interact with DNA but almost abolishes their poisoning effect on topoisomerase I. Unlike the vast majority of rebeccamycin analogues previously studied, the newly designed compounds do not stimulate DNA cleavage by topoisomerase I. The enhanced capacity of the 6'-amino glycosyl rebeccamycin derivatives to bind to DNA likely account for the improved biological profiles. DNA and topoisomerase I represent two independent targets which can both be used for the development of antitumor rebeccamycin derivatives. (C) 2003 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00343-2
• 作为产物：
  描述：

  12-(6-chloro-6-deoxy-4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 以83%的产率得到12-(6-azido-6-deoxy-4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione
  参考文献：
  名称：

  Rebeccamycin analogues bearing amine substituents or other groups on the sugar moiety

  摘要：

  In the course of structure-activity relationship studies on rebeccamycin analogues, a series of compounds bearing an amino function on the sugar moiety were synthesized with the aim of improving the solubility and interaction with the macromolecular target(s). The syntheses of amino derivatives and the corresponding chloro, iodo and azido intermediates are described. Their interaction with DNA and effects on human DNA topoisomerases I and II were investigated. Their antimicrobial activities against two Gram-positive bacteria, Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans were also determined. 6'-Amino compound 7 and 6'-N-methylamino 14 very efficiently inhibit the growth of E. coli. The introduction of an amino group at the 6'-position strongly enhances the capacity of the drugs to interact with DNA but almost abolishes their poisoning effect on topoisomerase I. Unlike the vast majority of rebeccamycin analogues previously studied, the newly designed compounds do not stimulate DNA cleavage by topoisomerase I. The enhanced capacity of the 6'-amino glycosyl rebeccamycin derivatives to bind to DNA likely account for the improved biological profiles. DNA and topoisomerase I represent two independent targets which can both be used for the development of antitumor rebeccamycin derivatives. (C) 2003 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00343-2