methyl 6-(imidazol-1-ylmethyl)-1-benzothiophene-2-carboxylate | 82801-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 6-(imidazol-1-ylmethyl)-1-benzothiophene-2-carboxylate
• CAS: 82801-17-0
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: CEFXYPPVSNWOIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 6-(imidazol-1-ylmethyl)-1-benzothiophene-2-carboxylate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以53%的产率得到6-Imidazol-1-ylmethyl-benzo[b]thiophene-2-carboxylic acid
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 3. 1H-Imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene- and indole-2- and 3-carboxylic acids

  摘要：

  The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).

  DOI：

  10.1021/jm00159a012
• 作为产物：
  描述：

  6-甲基苯并[b]噻吩-2-羧酸 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氯化碳 为溶剂， 反应 9.0h， 生成 methyl 6-(imidazol-1-ylmethyl)-1-benzothiophene-2-carboxylate
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 3. 1H-Imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene- and indole-2- and 3-carboxylic acids

  摘要：

  The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).

  DOI：

  10.1021/jm00159a012

文献信息

• CROSS P. E.; DICKINSON R. P.; PARRY M. J.; RANDALL M. J., J. MED. CHEM., 1986, 29, N 9, 1637-1643
  作者：CROSS P. E.、 DICKINSON R. P.、 PARRY M. J.、 RANDALL M. J.

  DOI：——

  日期：——