[6-(氮丙啶-1-基)-7-甲基-5,8-二氧代-2,3-二氢-1H-吡咯并[1,2-a]苯并咪唑-3-基]乙酸酯 | 123567-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [6-(氮丙啶-1-基)-7-甲基-5,8-二氧代-2,3-二氢-1H-吡咯并[1,2-a]苯并咪唑-3-基]乙酸酯
• 中文别名: C.I.反应的蛋黄95
• 英文名称: 6-N-aziridinyl-7-methyl-2,3-dihydro-1H-pyrrolo<1,2-a>benzimidazole-5,8-dione 3-acetate
• 英文别名: PBI-A；6-N-aziridinyl-7-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole-5,8-dione 3-acetate；6-N-Aziridinyl-3-hydrox-7-methyl-2,3-dihydro-1H-pyrrolo(1,2-a)benzimidazole-5,8-dione 3-acetate；[6-(aziridin-1-yl)-7-methyl-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-3-yl] acetate
• CAS: 123567-24-8
• 化学式: C₁₅H₁₅N₃O₄
• 分子量: 301.302
• InChiKey: FFUXDQVPXSUWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [6-(氮丙啶-1-基)-7-甲基-5,8-二氧代-2,3-二氢-1H-吡咯并[1,2-a]苯并咪唑-3-基]乙酸酯 在 palladium on activated charcoal pH 7.4 tris buffer 、 氢气 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 6-(1-氮丙啶基)-5,8-二羟基-7-甲基-2,3-二氢-1H-吡咯并[1,2-a]苯并咪唑-3-基乙酸酯
  参考文献：
  名称：

  A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo[1,2-a]benzimidazole and Pyrrolo[1,2-a]indole Ring Systems

  摘要：

  The cytotoxicity and physical properties of the pyrrolo[1,2-a]benzimidazole (PBI) and pyrrolo[1,2-a]indole (PI) aziridinyl quinones were compared in order to assess the influence of the benzimidazole ring on antitumor activity and DNA reductive alkylation. Our studies show that the PI system possesses none of the cytotoxicity of the PBI systems. Unlike the PBIs, the PI system does not reductively alkylate DNA. Apparently, the benzimidazole ring favors reductive alkylation due to its electron deficient character compared to indole. in addition, the benzimidazole ring may provide the hydrogen bonding interactions required for the interaction with DNA. Our findings resulted in the elucidation of a PBI pharmacophore. Inspection of the literature revealed another drug sharing the PBI pharmacophore, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione (EO9), which remarkably has cytotoxic properties similar to those of the PBIs

  DOI：

  10.1021/jm00037a013
• 作为产物：
  描述：

  乙烯亚胺 、 7-methyl-2,3-dihydro-1H-pyrrolo<1,2-a>benzimidazole-5,8-dione 3-acetate 以 甲醇 为溶剂， 以42%的产率得到[6-(氮丙啶-1-基)-7-甲基-5,8-二氧代-2,3-二氢-1H-吡咯并[1,2-a]苯并咪唑-3-基]乙酸酯
  参考文献：
  名称：

  Synthesis and physical studies of azamitosene and iminoazamitosene reductive alkylating agents. Iminoquinone hydrolytic stability, syn/anti isomerization, and electrochemistry

  摘要：

  DOI：

  10.1021/jo00297a040

文献信息

• ISLAM, IMADUL;SKIBO, EDWARD B., J. ORG. CHEM., 55,(1990) N0, C. 3195-3295
  作者：ISLAM, IMADUL、SKIBO, EDWARD B.

  DOI：——

  日期：——
• Boruah Romesh C., Skibo Edward B., J. Med. Chem, 37 (1994) N 11, S 1625-1631
  作者：Boruah Romesh C., Skibo Edward B.

  DOI：——

  日期：——
• Synthesis and physical studies of azamitosene and iminoazamitosene reductive alkylating agents. Iminoquinone hydrolytic stability, syn/anti isomerization, and electrochemistry
  作者：Imadul Islam、Edward B. Skibo

  DOI：10.1021/jo00297a040

  日期：1990.5
• A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo[1,2-a]benzimidazole and Pyrrolo[1,2-a]indole Ring Systems
  作者：Romesh C. Boruah、Edward B. Skibo

  DOI：10.1021/jm00037a013

  日期：1994.5

  The cytotoxicity and physical properties of the pyrrolo[1,2-a]benzimidazole (PBI) and pyrrolo[1,2-a]indole (PI) aziridinyl quinones were compared in order to assess the influence of the benzimidazole ring on antitumor activity and DNA reductive alkylation. Our studies show that the PI system possesses none of the cytotoxicity of the PBI systems. Unlike the PBIs, the PI system does not reductively alkylate DNA. Apparently, the benzimidazole ring favors reductive alkylation due to its electron deficient character compared to indole. in addition, the benzimidazole ring may provide the hydrogen bonding interactions required for the interaction with DNA. Our findings resulted in the elucidation of a PBI pharmacophore. Inspection of the literature revealed another drug sharing the PBI pharmacophore, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione (EO9), which remarkably has cytotoxic properties similar to those of the PBIs