2-{2-[5(6)-cyano(benzimidazolyl)]}-5-(4-cyanophenyl)thiophene | 796061-21-7

• 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: 2-{2-[5(6)-cyano(benzimidazolyl)]}-5-(4-cyanophenyl)thiophene
• CAS: 796061-21-7
• 化学式: C₁₉H₁₀N₄S
• 分子量: 326.381
• InChiKey: UPNPAYLYFKAVOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.26
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-{2-[5(6)-cyano(benzimidazolyl)]}-5-(4-cyanophenyl)thiophene 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 216.0h， 生成 2-{2-[5(6)-amidino]benzimidazolyl}-5-[(4-amidino)phenyl] thiophene trihydrochloride
  参考文献：
  名称：

  Thiophene-Based Diamidine Forms a “Super” AT Binding Minor Groove Agent

  摘要：

  The DNA minor groove is the interaction site for many enzymes and transcription control proteins and as a result, development of compounds that target the minor groove is an active research area. In an effort to develop biologically active minor groove agents, we are preparing and exploring the DNA interactions of a systematic set of diamidine derivatives with a powerful array of methods including DNase 1 footprinting, biosensor-SPR methods, and X-ray crystallography. Surprisingly, conversion of the parent phenyl-furan-phenyl diamidine to a phenyl-thiophene-benzimiclazole derivative yields a compound with over 10-fold-increased affinity for the minor groove at AT sequences. Single conversion of the furan to a thiophene or a phenyl to benzimidazole does not cause a similar increase in affinity. X-ray results indicate a small bond angle difference between the C-S-C angle of thiophene and the C-O-C angle of furan that, when amplified out to the terminal amidines of the benzimidazole compounds, yields a very significant difference in the positions of the amidines; and their DNA interaction strength.

  DOI：

  10.1021/ja048175m
• 作为产物：
  描述：

  在 盐酸 、 对苯醌 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 8.58h， 生成 2-{2-[5(6)-cyano(benzimidazolyl)]}-5-(4-cyanophenyl)thiophene
  参考文献：
  名称：

  Thiophene-Based Diamidine Forms a “Super” AT Binding Minor Groove Agent

  摘要：

  The DNA minor groove is the interaction site for many enzymes and transcription control proteins and as a result, development of compounds that target the minor groove is an active research area. In an effort to develop biologically active minor groove agents, we are preparing and exploring the DNA interactions of a systematic set of diamidine derivatives with a powerful array of methods including DNase 1 footprinting, biosensor-SPR methods, and X-ray crystallography. Surprisingly, conversion of the parent phenyl-furan-phenyl diamidine to a phenyl-thiophene-benzimiclazole derivative yields a compound with over 10-fold-increased affinity for the minor groove at AT sequences. Single conversion of the furan to a thiophene or a phenyl to benzimidazole does not cause a similar increase in affinity. X-ray results indicate a small bond angle difference between the C-S-C angle of thiophene and the C-O-C angle of furan that, when amplified out to the terminal amidines of the benzimidazole compounds, yields a very significant difference in the positions of the amidines; and their DNA interaction strength.

  DOI：

  10.1021/ja048175m