2-(3,4,5-trimethoxybenzylideneamino)benzimidazole | 679394-71-9

• 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-(3,4,5-trimethoxybenzylideneamino)benzimidazole
• 英文别名: (E)-N-(1H-1,3-benzodiazol-2-yl)-1-(3,4,5-trimethoxyphenyl)methanimine；N-(1H-benzimidazol-2-yl)-1-(3,4,5-trimethoxyphenyl)methanimine
• CAS: 679394-71-9
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: IIOAEWODAAGRSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4,5-trimethoxybenzylideneamino)benzimidazole 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 以18%的产率得到(1H-Benzoimidazol-2-yl)-(3,4,5-trimethoxy-benzyl)-amine
  参考文献：
  名称：

  Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives

  摘要：

  A novel series of Schiff bases 1-11, the derivatives of 2-aminobenzimidazole and substituted aromatic aldehydes, has been synthesised. Compounds 1-11 reduced by NaBH(4) formed 2-benzylaminobenzimidazoles 12-21. 2-(o-Bromobenzylamino)benzimidazole (15) acylated by cinnamoyl chloride gave 2-(o-bromobenzylamino)-1-cinnamoylbenzimidazole (22). Long heating of 15 and 19 with p-nitrocinnamoyl or cinnamoyl chloride led to the formation of pyrimido[1,2-a]benzimidazol-4-ones 23 and 24. The structures of 1-24 were identified by the results of elemental analysis and their IR, (1)H NMR and MS spectra. Among the compounds 1-24 evaluated for their antiproliferative activity in vitro, 16, 19, 20 and 22 exhibited cytotoxic activity against the cells of human cancer cell lines, namely SW707 (rectal), HCV29T (bladder), A549 (lung) and T47D (breast cancer).

  DOI：

  10.1016/j.farmac.2003.12.001
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 3,4,5-三甲氧基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 以15%的产率得到2-(3,4,5-trimethoxybenzylideneamino)benzimidazole
  参考文献：
  名称：

  Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives

  摘要：

  A novel series of Schiff bases 1-11, the derivatives of 2-aminobenzimidazole and substituted aromatic aldehydes, has been synthesised. Compounds 1-11 reduced by NaBH(4) formed 2-benzylaminobenzimidazoles 12-21. 2-(o-Bromobenzylamino)benzimidazole (15) acylated by cinnamoyl chloride gave 2-(o-bromobenzylamino)-1-cinnamoylbenzimidazole (22). Long heating of 15 and 19 with p-nitrocinnamoyl or cinnamoyl chloride led to the formation of pyrimido[1,2-a]benzimidazol-4-ones 23 and 24. The structures of 1-24 were identified by the results of elemental analysis and their IR, (1)H NMR and MS spectra. Among the compounds 1-24 evaluated for their antiproliferative activity in vitro, 16, 19, 20 and 22 exhibited cytotoxic activity against the cells of human cancer cell lines, namely SW707 (rectal), HCV29T (bladder), A549 (lung) and T47D (breast cancer).

  DOI：

  10.1016/j.farmac.2003.12.001

文献信息

• Nawrocka; Sztuba; Drys, Polish Journal of Chemistry, 2006, vol. 80, # 2, p. 279 - 287
  作者：Nawrocka、Sztuba、Drys、Wietrzyk、Kosendiak、Opolski

  DOI：——

  日期：——