2-(3-bromopropyl)-1H-indolo[1',7':4,5,6]pyrrolo[3',4':2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-dione | 1094276-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2-(3-bromopropyl)-1H-indolo[1',7':4,5,6]pyrrolo[3',4':2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-dione
• 英文别名: 13-(3-Bromopropyl)-10,13,16-triazahexacyclo[14.6.1.02,10.04,9.011,15.019,23]tricosa-1(22),2,4,6,8,11(15),17,19(23),20-nonaene-12,14-dione
• CAS: 1094276-69-3
• 化学式: C₂₃H₁₆BrN₃O₂
• 分子量: 446.303
• InChiKey: CPUVYCNOBDGSMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-bromopropyl)-1H-indolo[1',7':4,5,6]pyrrolo[3',4':2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-dione 、 N-甲硫脲 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 10.0h， 以50%的产率得到3-(1,3-dioxo-1,3-dihydro-2H-indolo[1',7':4,5,6]pyrrolo[3',4':2,3][1,4]diazepino[1,7-a]indol-2-yl)propyl N-methylimidothiocarbamate
  参考文献：
  名称：

  Search for Inhibitors of Bacterial and Human Protein Kinases among Derivatives of Diazepines[1,4] Annelated with Maleimide and Indole Cycles

  摘要：

  Aminomethylation of 9b,10-dihydro-1H-indolo[1,7:4,5,6]pyrrolo[3,4:2,3][1,4]diazepino-[1,7-a]indole-1,3(2H)-diones or 1H-indolo[1,7:4,5,6]pyrrolo[3,4:2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-diones resulted in dialkylaminomethyl derivatives. Alkylation of the nitrogen atom of maleimide moiety of polyannelated diazepines with 1,3-dibromopropane and subsequent reaction with thiourea or its N-alkyl derivatives gave isothiourea-carrying compounds. The compounds containing isothiourea moiety were active against individual human serine/threonine and tyrosine kinases at low micromolar concentrations. Dialkylaminomethyl derivatives of diazepines sensitized Streptomyces lividans with overexpressed aminoglycoside phosphotransferase type VIII (aphVIII) to kanamycin by inhibiting serine/threonine kinase(s) mediated aphVIII phosphorylation.

  DOI：

  10.1021/jm800758s
• 作为产物：
  描述：

  1,3-二溴丙烷 、 1H-indolo[1',7':4,5,6]pyrrolo[3',4':2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-dione 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以60%的产率得到2-(3-bromopropyl)-1H-indolo[1',7':4,5,6]pyrrolo[3',4':2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-dione
  参考文献：
  名称：

  Search for Inhibitors of Bacterial and Human Protein Kinases among Derivatives of Diazepines[1,4] Annelated with Maleimide and Indole Cycles

  摘要：

  Aminomethylation of 9b,10-dihydro-1H-indolo[1,7:4,5,6]pyrrolo[3,4:2,3][1,4]diazepino-[1,7-a]indole-1,3(2H)-diones or 1H-indolo[1,7:4,5,6]pyrrolo[3,4:2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-diones resulted in dialkylaminomethyl derivatives. Alkylation of the nitrogen atom of maleimide moiety of polyannelated diazepines with 1,3-dibromopropane and subsequent reaction with thiourea or its N-alkyl derivatives gave isothiourea-carrying compounds. The compounds containing isothiourea moiety were active against individual human serine/threonine and tyrosine kinases at low micromolar concentrations. Dialkylaminomethyl derivatives of diazepines sensitized Streptomyces lividans with overexpressed aminoglycoside phosphotransferase type VIII (aphVIII) to kanamycin by inhibiting serine/threonine kinase(s) mediated aphVIII phosphorylation.

  DOI：

  10.1021/jm800758s

文献信息

• Search for Inhibitors of Bacterial and Human Protein Kinases among Derivatives of Diazepines[1,4] Annelated with Maleimide and Indole Cycles
  作者：Valery N. Danilenko、Alexander Y. Simonov、Sergey A. Lakatosh、Michael H. G. Kubbutat、Frank Totzke、Christoph Schächtele、Sergey M. Elizarov、Olga B. Bekker、Svetlana S. Printsevskaya、Yuryi N. Luzikov、Marina I. Reznikova、Alexander A. Shtil、Maria N. Preobrazhenskaya

  DOI：10.1021/jm800758s

  日期：2008.12.25

  Aminomethylation of 9b,10-dihydro-1H-indolo[1,7:4,5,6]pyrrolo[3,4:2,3][1,4]diazepino-[1,7-a]indole-1,3(2H)-diones or 1H-indolo[1,7:4,5,6]pyrrolo[3,4:2,3][1,4]diazepino[1,7-a]indole-1,3(2H)-diones resulted in dialkylaminomethyl derivatives. Alkylation of the nitrogen atom of maleimide moiety of polyannelated diazepines with 1,3-dibromopropane and subsequent reaction with thiourea or its N-alkyl derivatives gave isothiourea-carrying compounds. The compounds containing isothiourea moiety were active against individual human serine/threonine and tyrosine kinases at low micromolar concentrations. Dialkylaminomethyl derivatives of diazepines sensitized Streptomyces lividans with overexpressed aminoglycoside phosphotransferase type VIII (aphVIII) to kanamycin by inhibiting serine/threonine kinase(s) mediated aphVIII phosphorylation.