ethyl 5-hydroxy-2-(naphthalen-2-yl)-1-benzofuran-3-carboxylate | 1390638-35-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: ethyl 5-hydroxy-2-(naphthalen-2-yl)-1-benzofuran-3-carboxylate
• CAS: 1390638-35-3
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: TVMYKCCWUDMPQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-2-(naphthalen-2-yl)-1-benzofuran-3-carboxylate 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 0.17h， 生成 5-[(4-bromobenzyl)oxy]-2-(2-naphthyl)-1-benzofuran-3-carboxylic acid
  参考文献：
  名称：

  Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors

  摘要：

  Transmembrane protein 16A (TMEM16A) channels are recently discovered membrane proteins that functions as a calcium activated chloride channel (CaCC). CaCCs are major regulators of various physiological processes, such as sensory transduction, epithelial secretion, smooth muscle contraction and oocyte fertilization. Thirty novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids (B01-B30) were synthesized and evaluated for their TMEM16A inhibitory activity by using short circuit current measurements in Fischer rat thyroid (FRT) cells expressing human TMEM16A. IC50 values were calculated using YFP fluorescence plate reader assay. Final compounds, having free carboxylic group displayed significant inhibition. Eight of the novel compounds B02, B13, B21, B23, B25, B27, B28, B29 exhibit excellent CaCCs inhibition with IC50 value <6 mu M, with compound B25 exhibiting the lowest IC50 value of 2.8 +/- 1.3 mu M. None of the tested ester analogs of final benzofuran derivatives displayed TMEM16A/CaCCs inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.074
• 作为产物：
  描述：

  3-萘-3-氧丙酸乙酯 、 对苯醌 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到ethyl 5-hydroxy-2-(naphthalen-2-yl)-1-benzofuran-3-carboxylate
  参考文献：
  名称：

  Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors

  摘要：

  Transmembrane protein 16A (TMEM16A) channels are recently discovered membrane proteins that functions as a calcium activated chloride channel (CaCC). CaCCs are major regulators of various physiological processes, such as sensory transduction, epithelial secretion, smooth muscle contraction and oocyte fertilization. Thirty novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids (B01-B30) were synthesized and evaluated for their TMEM16A inhibitory activity by using short circuit current measurements in Fischer rat thyroid (FRT) cells expressing human TMEM16A. IC50 values were calculated using YFP fluorescence plate reader assay. Final compounds, having free carboxylic group displayed significant inhibition. Eight of the novel compounds B02, B13, B21, B23, B25, B27, B28, B29 exhibit excellent CaCCs inhibition with IC50 value <6 mu M, with compound B25 exhibiting the lowest IC50 value of 2.8 +/- 1.3 mu M. None of the tested ester analogs of final benzofuran derivatives displayed TMEM16A/CaCCs inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.074