2-(3'-methoxybiphenyl-3-yl)-1-benzothiophene | 1233720-86-9

• 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: 2-(3'-methoxybiphenyl-3-yl)-1-benzothiophene
• CAS: 1233720-86-9
• 化学式: C₂₁H₁₆OS
• 分子量: 316.423
• InChiKey: QGSLYEQTUSHRMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(3'-methoxybiphenyl-3-yl)-1-benzothiophene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以77%的产率得到3'-(1-benzothien-2-yl)biphenyl-3-ol
  参考文献：
  名称：

  Novel estrone mimetics with high 17β-HSD1 inhibitory activity

  摘要：

  17 beta-Hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) catalyzes the reduction of estrone into estradiol, which is the most potent estrogen in humans. Lowering intracellular estradiol concentration by inhibition of this enzyme is a promising new option for the treatment of estrogen-dependent diseases like breast cancer and endometriosis. Combination of ligand- and structure-based design resulted in heterocyclic substituted biphenylols and their aza-analogs as new 17 beta-HSD1 inhibitors. The design was based on mimicking estrone, especially focusing on the imitation of the D-ring keto group with (substituted) heterocycles. Molecular docking provided insights into plausible protein-ligand interactions for this class of compounds. The most promising compound 12 showed an inhibitory activity in the high nanomolar range and very low affinity for the estrogen receptors alpha and beta. Thus, compound 12 is a novel tool for the elucidation of the pharmacological relevance of 17 beta-HSD1 and might be a lead for the treatment of estrogen-dependent diseases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.065
• 作为产物：
  描述：

  3'-溴-3-甲氧基联苯 、 苯并噻吩-2-硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 150.0 ℃ 、1.5 MPa 条件下， 反应 0.25h， 以47%的产率得到2-(3'-methoxybiphenyl-3-yl)-1-benzothiophene
  参考文献：
  名称：

  Novel estrone mimetics with high 17β-HSD1 inhibitory activity

  摘要：

  17 beta-Hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) catalyzes the reduction of estrone into estradiol, which is the most potent estrogen in humans. Lowering intracellular estradiol concentration by inhibition of this enzyme is a promising new option for the treatment of estrogen-dependent diseases like breast cancer and endometriosis. Combination of ligand- and structure-based design resulted in heterocyclic substituted biphenylols and their aza-analogs as new 17 beta-HSD1 inhibitors. The design was based on mimicking estrone, especially focusing on the imitation of the D-ring keto group with (substituted) heterocycles. Molecular docking provided insights into plausible protein-ligand interactions for this class of compounds. The most promising compound 12 showed an inhibitory activity in the high nanomolar range and very low affinity for the estrogen receptors alpha and beta. Thus, compound 12 is a novel tool for the elucidation of the pharmacological relevance of 17 beta-HSD1 and might be a lead for the treatment of estrogen-dependent diseases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.065