N-[4-(5-Dimethylaminomethyl-1H-pyrrol-3-yl)-thiazol-2-yl]-guanidine | 115027-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[4-(5-Dimethylaminomethyl-1H-pyrrol-3-yl)-thiazol-2-yl]-guanidine
• 英文别名: 2-[4-[5-[(dimethylamino)methyl]-1H-pyrrol-3-yl]-1,3-thiazol-2-yl]guanidine
• CAS: 115027-68-4
• 化学式: C₁₁H₁₆N₆S
• 分子量: 264.354
• InChiKey: JWXQIRLTOMCOMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  脒基硫脲 、 2-Chloro-1-(5-dimethylaminomethyl-1H-pyrrol-3-yl)-ethanone 以 乙醇 为溶剂， 生成 N-[4-(5-Dimethylaminomethyl-1H-pyrrol-3-yl)-thiazol-2-yl]-guanidine
  参考文献：
  名称：

  Antiulcer agents. 4-Substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K+-ATPase

  摘要：

  A series of 4-substituted 2-guanidinothiazoles has been found to inhibit the gastric proton-pump enzyme H+,K(+)-ATPase. In general, these compounds were reversible inhibitors of canine gastric H+,K(+)-ATPase, competitive at the K+ site, and selective relative to canine renal Na+,K(+)-ATPase. Structure-activity relationship (SAR) studies on this series revealed no general replacement for the guanidinothiazole. On the other hand, use of pyrrolyl, phenyl, and indolyl groups as the C-4 substituent yielded active compounds. Extensive studies of substitution patterns on these 4-aryl groups led to more active compounds, but no consistent SAR became apparent. Monosubstitution of the guanidine and substitution of the thiazole at C-5 both often led to increased activity, but combining these changes generated compounds less active than the parents. Despite 100-fold improvement in in vitro inhibitory potency, only a 3-fold increase in gastric antisecretory activity in rats was observed for these agents.

  DOI：

  10.1021/jm00164a012