bis(benzotriazol-1-yl) 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate | 911208-95-2

• 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: bis(benzotriazol-1-yl) 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate
• 英文别名: Bis(benzotriazol-1-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-dicarboxylate；bis(benzotriazol-1-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-dicarboxylate
• CAS: 911208-95-2；911208-97-4；552318-09-9
• 化学式: C₂₇H₂₂N₁₀O₄
• 分子量: 550.536
• InChiKey: XNIWQYIHLQXYPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  bis(benzotriazol-1-yl) 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  含有N-甲基吡咯单元的新型杂环Tröger碱衍生物

  摘要：

  从4-氨基-N-甲基吡咯羧酸盐区域选择性地制备Tröger碱的新型类似物，收率很高。二苄基-4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ]的催化加氢[1,5]二唑-2,7-二羧酸盐2b导致4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ] [1,5]二唑-2,7-二羧酸3它通过酰胺方案用于制备Tröger天然抗生素的基础衍生物。通过多种光谱技术和化合物2b通过X射线晶体学表征了新型的Tröger杂环碱基。在N-甲基吡咯Tröger的基本骨架中引入胍作为末端基团，为制备水溶性衍生物提供了可能。

  DOI：

  10.1016/s0040-4039(03)00177-1
• 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 15.0h， 生成 bis(benzotriazol-1-yl) 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate
  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.
• Novel heterocyclic Tröger's base derivatives containing N-methylpyrrole units
  作者：Martin Valı&#x;k、Bohumil Dolensky、Hana Petřı&#x;čková、Petr Vašek、Vladimı&#x;r Král

  DOI：10.1016/s0040-4039(03)00177-1

  日期：2003.3

  preparation of Tröger's base derivatives of natural antibiotics via an amide protocol. The novel heterocyclic Tröger's bases were characterized by a variety of spectroscopic techniques and compound 2b by X-ray crystallography. Incorporation of guanidine as the terminal group in the N-methylpyrrole Tröger's base skeleton opens the possibility for preparation of water soluble derivatives.

  从4-氨基-N-甲基吡咯羧酸盐区域选择性地制备Tröger碱的新型类似物，收率很高。二苄基-4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ]的催化加氢[1,5]二唑-2,7-二羧酸盐2b导致4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ] [1,5]二唑-2,7-二羧酸3它通过酰胺方案用于制备Tröger天然抗生素的基础衍生物。通过多种光谱技术和化合物2b通过X射线晶体学表征了新型的Tröger杂环碱基。在N-甲基吡咯Tröger的基本骨架中引入胍作为末端基团，为制备水溶性衍生物提供了可能。