2-Methyl-4-(5-methyl-1H-pyrrol-3-yl)-thiazole | 123309-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Methyl-4-(5-methyl-1H-pyrrol-3-yl)-thiazole
• 英文别名: 2-methyl-4-(5-methyl-1H-pyrrol-3-yl)-1,3-thiazole
• CAS: 123309-49-9
• 化学式: C₉H₁₀N₂S
• 分子量: 178.258
• InChiKey: BIZKSGYXSKWWKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-氯乙酰基)-1H-吡咯-2-甲醛 在 盐酸 、 diborane(6) 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-Methyl-4-(5-methyl-1H-pyrrol-3-yl)-thiazole
  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