1-Amino-3-benzyl-2-methylbenzimidazolium mesitylenesulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Amino-3-benzyl-2-methylbenzimidazolium mesitylenesulfonate
• 英文别名: 3-Benzyl-2-methylbenzimidazol-3-ium-1-amine;2,4,6-trimethylbenzenesulfonate
• 化学式: C₉H₁₁O₃S*C₁₅H₁₆N₃
• 分子量: 437.563
• InChiKey: WNAKWARJAMEVFY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Amino-3-benzyl-2-methylbenzimidazolium mesitylenesulfonate 、 1-苯基-1,2-丙二酮 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以60%的产率得到5-Benzyl-2-methyl-3-phenylpyridazino<1,6-a>benzimidazolium mesitylenesulfonate
  参考文献：
  名称：

  Regioselectivity in the Westphal Condensation

  摘要：

  DOI：

  10.1021/jo00105a062
• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰羟胺 、 1-苄基-2-甲基-1H-苯并[d]咪唑 以 二氯甲烷 为溶剂， 反应 0.17h， 以86%的产率得到1-Amino-3-benzyl-2-methylbenzimidazolium mesitylenesulfonate
  参考文献：
  名称：

  Azino-Fused Benzimidazolium Salts as DNA Intercalating Agents. 2.

  摘要：

  The synthesis of new pyrido[1,2-a]- and pyridazino[1,6-a]benzimidazolium salts by basic condensation of 1,3-disubstituted 2-alkylbenzimidazolium salts and 1,2-diketones and subsequent chemical transformations is described. The DNA-binding properties were examined by UV-vis spectroscopy, viscosimetric determinations, and molecular modeling techniques. The presence of a flat polycyclic hydrocarbon moiety such as a naphthalene-1,8-diyl or a biphenyl-o,o'-diyl, fused to the cationic heterocycle, appears to enhance the interaction with DNA. Variation of the substituents on the indole-like N will allow us to build up a new series of his-salts with bis-intercalating properties.

  DOI：

  10.1021/jo962055i

文献信息

• Regioselectivity in the Westphal Condensation
  作者：Adolfo Diaz、Maria P. Matia、Jose L. Garcia-Navio、Juan J. Vaquero、Julio Alvarez-Builla

  DOI：10.1021/jo00105a062

  日期：1994.12
• Azino-Fused Benzimidazolium Salts as DNA Intercalating Agents. 2.
  作者：Joaquín Pastor、Jorge G. Siro、José L. García-Navío、Juan J. Vaquero、Julio Alvarez-Builla、Federico Gago、Beatriz de Pascual-Teresa、Manuel Pastor、M. Melia Rodrigo

  DOI：10.1021/jo962055i

  日期：1997.8.1

  The synthesis of new pyrido[1,2-a]- and pyridazino[1,6-a]benzimidazolium salts by basic condensation of 1,3-disubstituted 2-alkylbenzimidazolium salts and 1,2-diketones and subsequent chemical transformations is described. The DNA-binding properties were examined by UV-vis spectroscopy, viscosimetric determinations, and molecular modeling techniques. The presence of a flat polycyclic hydrocarbon moiety such as a naphthalene-1,8-diyl or a biphenyl-o,o'-diyl, fused to the cationic heterocycle, appears to enhance the interaction with DNA. Variation of the substituents on the indole-like N will allow us to build up a new series of his-salts with bis-intercalating properties.