N-Benzyl-N'-[4-(3-methoxy-phenyl)-thiazol-2-yl]-guanidine; hydrobromide | 123310-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-Benzyl-N'-[4-(3-methoxy-phenyl)-thiazol-2-yl]-guanidine; hydrobromide
• 英文别名: 2-Benzyl-1-[4-(3-methoxyphenyl)-1,3-thiazol-2-yl]guanidine;hydrobromide
• CAS: 123310-83-8
• 化学式: BrH*C₁₈H₁₈N₄OS
• 分子量: 419.345
• InChiKey: KGBWXLCQCFRCDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(N-benzylguanyl)thiourea 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 生成 N-Benzyl-N'-[4-(3-methoxy-phenyl)-thiazol-2-yl]-guanidine; hydrobromide
  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

文献信息

• Antiulcer agents. 4-Substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K+-ATPase
  作者：John L. LaMattina、Peter A. McCarthy、Lawrence A. Reiter、William F. Holt、Li An Yeh

  DOI：10.1021/jm00164a012

  日期：1990.2

  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.