1-(1H-benzo[d]imidazol-2-yl)-3-((1-methyl-1H-pyrrol-2-yl)methylene)guanidine | 1254984-12-7

• 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: 1-(1H-benzo[d]imidazol-2-yl)-3-((1-methyl-1H-pyrrol-2-yl)methylene)guanidine
• 英文别名: 2-(1H-benzimidazol-2-yl)-1-[(1-methylpyrrol-2-yl)methylidene]guanidine
• CAS: 1254984-12-7
• 化学式: C₁₄H₁₄N₆
• 分子量: 266.305
• InChiKey: JGKWZDQVURWZSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.85
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 2-胍基苯并咪唑 反应 0.2h， 以87%的产率得到1-(1H-benzo[d]imidazol-2-yl)-3-((1-methyl-1H-pyrrol-2-yl)methylene)guanidine
  参考文献：
  名称：

  Conventional and microwave-assisted synthesis of imidazole and guanidine derivatives and their biological evaluation

  摘要：

  A number of imidazole derivatives 3a-f and 4a-f have been synthesized by the condensation of 3-methylthiophen-2-carboxaldehyde 1a, 5-methylthiophen-2-carboxaldehyde 1b, N-methylpyrrol-2-carboxaldehyde 1c, 1-naphthaldehyde 1d, 2-naphthaldehyde 1e, and 2-hydroxy-1-naphthaldehyde 1f with 1,2-diaminoanthraquinone 2a and 2,3-diaminophenazine 2b, respectively. Condensation of 2-guanidinobenzimidazole with functionalized aldehydes 1a-f leads to the formation of guanidine derivatives 5a-f. Both imidazole (3a-f, 4a-f) and guanidine derivatives (5a-f) were synthesized in good yields using conventional heating and microwave irradiation techniques. Structures assigned to compounds 3a-f, 4a-f and 5a-f are supported by correct spectral and analytic data. On screening for anti-inflammatory and anticancer activities, compounds 3e, 4a and 5a exhibited good anti-inflammatory and compounds 3d, 3f, 4d and 4f showed very good anticancer activity.

  DOI：

  10.1007/s00044-010-9410-6