4-N,11-N-bis[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-5,12-dimethyl-1,5,8,12-tetrazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-N,11-N-bis[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-5,12-dimethyl-1,5,8,12-tetrazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarboxamide
• 化学式: C₆₁H₇₆N₂₀O₈
• 分子量: 1217.4
• InChiKey: BAKMCIAGXIAVHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  89
• 可旋转键数：
  22
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  285
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  bis(1-phenylethyl)-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-4,9-methanodipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.3 kPa 条件下， 反应 20.0h， 生成 4-N,11-N-bis[5-[[5-[[5-[3-(dimethylamino)propylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-5,12-dimethyl-1,5,8,12-tetrazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarboxamide
  参考文献：
  名称：

  Tröger's base scaffold in racemic and chiral fashion as a spacer for bisdistamycin formation. Synthesis and DNA binding study

  摘要：

  Head-to-head' oligo-N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT)(2), and poly(dC-dG)(2) by NMR and ECD spectroscopies, and fluorescence probe displacement assay. The presented dimers prefer AT sequences, but show higher affinity to poly(dC-dG)(2) than distamycin A. The (4R,9R) configuration of methanodiazocin bridge was found to be better suited for interaction with ct-DNA and poly(dA-dT)(2) than (4S,9S) configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.056

文献信息

• Tröger's base scaffold in racemic and chiral fashion as a spacer for bisdistamycin formation. Synthesis and DNA binding study
  作者：Martin Valík、Jaroslav Malina、Lukáš Palivec、Jarmila Foltýnová、Marcela Tkadlecová、Marie Urbanová、Viktor Brabec、Vladimír Král

  DOI：10.1016/j.tet.2006.06.056

  日期：2006.9

  Head-to-head' oligo-N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT)(2), and poly(dC-dG)(2) by NMR and ECD spectroscopies, and fluorescence probe displacement assay. The presented dimers prefer AT sequences, but show higher affinity to poly(dC-dG)(2) than distamycin A. The (4R,9R) configuration of methanodiazocin bridge was found to be better suited for interaction with ct-DNA and poly(dA-dT)(2) than (4S,9S) configuration. (c) 2006 Elsevier Ltd. All rights reserved.