3-(1H-Imidazol-4-yl)-N-methyl-benzamidine | 88304-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1H-Imidazol-4-yl)-N-methyl-benzamidine
• 英文别名: 3-(1H-imidazol-5-yl)-N'-methylbenzenecarboximidamide
• CAS: 88304-65-8
• 化学式: C₁₁H₁₂N₄
• 分子量: 200.243
• InChiKey: UABADXCDOOWABX-UHFFFAOYSA-N

物化性质

• 沸点：
  444.4±47.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-溴乙酰基)苯甲腈 以 水 为溶剂， 反应 9.0h， 生成 3-(1H-Imidazol-4-yl)-N-methyl-benzamidine
  参考文献：
  名称：

  (Imidazolylphenyl)formamidines. A structurally novel class of potent histamine H2 receptor antagonists

  摘要：

  Structure-activity considerations of N alpha-guanylhistamine, the first compound found with detectable H2-antagonist activity, led to the synthesis of a series of conformationally rigid guanylhistamine analogues, namely, (imidazolylphenyl)guanidines, imidazolylbenzamidines, and (imidazolylphenyl)formamidines. It was found that in the guanidine and benzamidine classes, the meta-substituted derivatives (3, 4, 7, and 8) possessed H2-antagonist activity, whereas in the class of formamidines, only the para-substituted derivative 10 was found active. A subsequent increase in the size of the substituent at the formamidino group of 10 led to compounds (15-20) of high H2-antagonist affinity, which was related to the gastric antisecretory effect. Members of this structurally novel class of H2 antagonists were 20- to 50-fold more potent than cimetidine both "in vitro" and "in vivo". Structure-activity relationships are discussed in terms of ionization properties, partitioning behavior, conformational aspects of the selected compound 17, and of possible modes of interaction with the histamine H2 receptor. It was found that the formamidine moiety was an important structural feature and that H2-antagonist activity requires correct steric and electronic properties. Compound 17 (DA 4577), owing to its pharmacological profile and demonstrated safety in animals, was selected to be clinically investigated.

  DOI：

  10.1021/jm00369a025