4-[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazol-2-yl]benzene-1,2-diamine | 732966-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazol-2-yl]benzene-1,2-diamine
• CAS: 732966-18-6
• 化学式: C₁₆H₁₆N₆
• 分子量: 292.343
• InChiKey: FIUPCDCVPMLPJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  己二酸 、 4-[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazol-2-yl]benzene-1,2-diamine 在 盐酸 作用下， 反应 168.0h， 以30%的产率得到1,2-bis[5-[5'-(2-imidazolinyl)-2'-benzimidazolyl]-2-benzimidazolyl]butane
  参考文献：
  名称：

  Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections

  摘要：

  Considerable evidence now indicates that DNA is the receptor site for dicationic benzimidazole anti-opportunistic infections agents (Bell, C. A.; Dykstra, C. C.; Naiman, N. A. I.; Cory, M:.; Fairley, T. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1993, 37, 2668-2673. Tidwell, R. R.; Jones, S. K; Naiman, N. A.; Berger, I. C.; Brake, W. R.; Dykstra, C, C.; Hall, J. E. Antimicrob. Agents Chemother. 1993, 37, 1713-1716). To obtain additional information on benzimidazole-receptor complexes, the syntheses and DNA interactions of series of symmetric benzimidazole cations, linked by alkyl or alkenyl groups, have been evaluated. Biophysical techniques, thermal denaturation measurement (Delta T-m), kinetics, and circular dichroism (CD) have been used in conjunction with NMR and molecular modeling to evaluate the affinities, binding mode, and structure of complexes formed between these compounds and DNA. All of the compounds bind strongly to DNA samples with four or more consecutive AT base pairs, and they bind negligibly to GC rich DNA or to RNA. Spectral and kinetics characteristics of the benzimidazole complexes indicate that the compounds bind in the DNA minor groove at AT sequences. NMR and molecular modeling of the complex formed between an ethylene-linked benzimidazole derivative, 5, and the self-complementary oligomer d(GCGAATTCGC) have been used to establish structural details for the minor groove complex. These results have been used as a starting point for molecular mechanics calculations to refine the model of the minor groove-benzimidazole complex and to draw conclusions regarding the molecular basis for the effects of substituent changes on benzimidazole-DNA affinities.

  DOI：

  10.1021/jm9507946
• 作为产物：
  描述：

  4-[N-(2-imidazolinyl)]-1,2-phenylenediamine 在 palladium on activated charcoal 盐酸 、 氢气 、 对苯醌 作用下， 以 乙醇 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 6.5h， 生成 4-[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazol-2-yl]benzene-1,2-diamine
  参考文献：
  名称：

  Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections

  摘要：

  Considerable evidence now indicates that DNA is the receptor site for dicationic benzimidazole anti-opportunistic infections agents (Bell, C. A.; Dykstra, C. C.; Naiman, N. A. I.; Cory, M:.; Fairley, T. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1993, 37, 2668-2673. Tidwell, R. R.; Jones, S. K; Naiman, N. A.; Berger, I. C.; Brake, W. R.; Dykstra, C, C.; Hall, J. E. Antimicrob. Agents Chemother. 1993, 37, 1713-1716). To obtain additional information on benzimidazole-receptor complexes, the syntheses and DNA interactions of series of symmetric benzimidazole cations, linked by alkyl or alkenyl groups, have been evaluated. Biophysical techniques, thermal denaturation measurement (Delta T-m), kinetics, and circular dichroism (CD) have been used in conjunction with NMR and molecular modeling to evaluate the affinities, binding mode, and structure of complexes formed between these compounds and DNA. All of the compounds bind strongly to DNA samples with four or more consecutive AT base pairs, and they bind negligibly to GC rich DNA or to RNA. Spectral and kinetics characteristics of the benzimidazole complexes indicate that the compounds bind in the DNA minor groove at AT sequences. NMR and molecular modeling of the complex formed between an ethylene-linked benzimidazole derivative, 5, and the self-complementary oligomer d(GCGAATTCGC) have been used to establish structural details for the minor groove complex. These results have been used as a starting point for molecular mechanics calculations to refine the model of the minor groove-benzimidazole complex and to draw conclusions regarding the molecular basis for the effects of substituent changes on benzimidazole-DNA affinities.

  DOI：

  10.1021/jm9507946

文献信息

• Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections
  作者：Richard L. Lombardy、Farial A. Tanious、Kishore Ramachandran、Richard R. Tidwell、W. David Wilson

  DOI：10.1021/jm9507946

  日期：1996.1.1

  Considerable evidence now indicates that DNA is the receptor site for dicationic benzimidazole anti-opportunistic infections agents (Bell, C. A.; Dykstra, C. C.; Naiman, N. A. I.; Cory, M:.; Fairley, T. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1993, 37, 2668-2673. Tidwell, R. R.; Jones, S. K; Naiman, N. A.; Berger, I. C.; Brake, W. R.; Dykstra, C, C.; Hall, J. E. Antimicrob. Agents Chemother. 1993, 37, 1713-1716). To obtain additional information on benzimidazole-receptor complexes, the syntheses and DNA interactions of series of symmetric benzimidazole cations, linked by alkyl or alkenyl groups, have been evaluated. Biophysical techniques, thermal denaturation measurement (Delta T-m), kinetics, and circular dichroism (CD) have been used in conjunction with NMR and molecular modeling to evaluate the affinities, binding mode, and structure of complexes formed between these compounds and DNA. All of the compounds bind strongly to DNA samples with four or more consecutive AT base pairs, and they bind negligibly to GC rich DNA or to RNA. Spectral and kinetics characteristics of the benzimidazole complexes indicate that the compounds bind in the DNA minor groove at AT sequences. NMR and molecular modeling of the complex formed between an ethylene-linked benzimidazole derivative, 5, and the self-complementary oligomer d(GCGAATTCGC) have been used to establish structural details for the minor groove complex. These results have been used as a starting point for molecular mechanics calculations to refine the model of the minor groove-benzimidazole complex and to draw conclusions regarding the molecular basis for the effects of substituent changes on benzimidazole-DNA affinities.