1,2-bis[5-[5'-(2-imidazolinyl)-2'-benzimidazolyl]-2-benzimidazolyl]ethane

• 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: 1,2-bis[5-[5'-(2-imidazolinyl)-2'-benzimidazolyl]-2-benzimidazolyl]ethane
• 英文别名: 6-(4,5-dihydro-1H-imidazol-2-yl)-2-[2-[2-[6-[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]ethyl]-3H-benzimidazol-5-yl]-1H-benzimidazole
• 化学式: C₃₆H₃₀N₁₂
• 分子量: 630.715
• InChiKey: ADFHRJBEOFOFAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 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 174.5h， 生成 1,2-bis[5-[5'-(2-imidazolinyl)-2'-benzimidazolyl]-2-benzimidazolyl]ethane
  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

• Amidine derivatives for treating amyloidosis
  申请人：Chalifour J. Robert

  公开号：US20070021483A1

  公开（公告）日：2007-01-25

  The present invention relates to the use of amidine compounds in the treatment of amyloid-related diseases. In particular, the invention relates to a method of treating or preventing an amyloid-related disease in a subject comprising administering to the subject a therapeutic amount of an amidine compound. Among the compounds for use according to the invention are those according to the following Formula, such that, when administered, amyloid fibril formation, neurodegeneration, or cellular toxicity is reduced or inhibited:

  本发明涉及在治疗与淀粉样相关疾病中使用氨基脲类化合物。特别地，本发明涉及一种治疗或预防受试者淀粉样相关疾病的方法，包括向受试者施用治疗剂量的氨基脲类化合物。根据本发明使用的化合物包括以下化学式的化合物，当施用时，可减少或抑制淀粉样纤维形成、神经退行性或细胞毒性：
• 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.