Ethyl4-(benzyloxy)-3-methylbenzofuran-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Ethyl4-(benzyloxy)-3-methylbenzofuran-2-carboxylate
• 英文别名: ethyl 3-methyl-4-phenylmethoxy-1-benzofuran-2-carboxylate
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: ZGCFWUMNDDAIDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl4-(benzyloxy)-3-methylbenzofuran-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以62%的产率得到4-(benzyloxy)-3-methylbenzofuran-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzofuran derivatives as ET receptor antagonists

  摘要：

  A series of novel benzofuran carboxylic acid derivatives have been designed and synthesized, with their antagonism effect screened on ET-1-induced contraction in the rat thoracic aortic ring. Some target compounds demonstrated significant inhibitory activity, especially benzo[c]thiadiazole and benzo[c]oxadiazole compounds 29 and 30 showed potent inhibition percentage higher than the contrast compound BQ123. Further affinity and selectivity for ET binding assay showed that 29 demonstrated a dual ETA/ETB antagonism activity in nanomole level. Moreover, 30 was effective in relieving hypoxia-induced pulmonary arterial hypertension.

  DOI：

  10.1007/s00044-013-0542-3
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 乙醇 、 sodium 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.0h， 生成 Ethyl4-(benzyloxy)-3-methylbenzofuran-2-carboxylate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzofuran derivatives as ET receptor antagonists

  摘要：

  A series of novel benzofuran carboxylic acid derivatives have been designed and synthesized, with their antagonism effect screened on ET-1-induced contraction in the rat thoracic aortic ring. Some target compounds demonstrated significant inhibitory activity, especially benzo[c]thiadiazole and benzo[c]oxadiazole compounds 29 and 30 showed potent inhibition percentage higher than the contrast compound BQ123. Further affinity and selectivity for ET binding assay showed that 29 demonstrated a dual ETA/ETB antagonism activity in nanomole level. Moreover, 30 was effective in relieving hypoxia-induced pulmonary arterial hypertension.

  DOI：

  10.1007/s00044-013-0542-3