(4-ethylphenyl)(6-methoxybenzofuran-2-yl)methanone | 878196-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-ethylphenyl)(6-methoxybenzofuran-2-yl)methanone
• 英文别名: (4-Ethylphenyl)-(6-methoxy-1-benzofuran-2-yl)methanone
• CAS: 878196-25-9
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: ZXTSSIRQKVKMAH-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±35.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-ethylphenyl)(6-methoxybenzofuran-2-yl)methanone 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (4-ethylphenyl)(6-methoxybenzofuran-2-yl)methanol
  参考文献：
  名称：

  Potent CYP19 (Aromatase) 1-[(Benzofuran-2-yl)(phenylmethyl)pyridine, -imidazole, and -triazole Inhibitors:  Synthesis and Biological Evaluation

  摘要：

  The synthesis of a series of novel 1-[(benzofuran-2-yl)phenylmethyl]-pyridine, -imidazole, and -triazole derivatives is described. All the compounds were evaluated in vitro for inhibitory activity against aromatase (P450(AROM), CYP19), using human placental microsomes. The 6-methoxy- and 6-hydroxy-substituted benzofuran derivatives were shown to be potent CYP19 inhibitors (IC50 = 0.01-1.46 mu M) with activity greater than that observed for the unsubstituted parent compounds and inhibitory activity comparable with or greater than the reference compound arimidex (IC50 = 0.6 mu M). Six of the benzofuran derivatives were subjected to in vitro cytotoxicity assays, using rat liver hepatocytes with cytotoxicity determined from alteration in cell morphology and lactate dehydrogenase enzyme retention over a period of 24 h, and selectivity (CYP17, 17 beta-HSD types 1 and 3, CYP24, and CYP26) determination; negligible inhibitory activity was observed, suggesting a good selectivity for CYP19. The pyridine benzofuran 4a containing the 4-fluorophenyl group was the most promising (IC50 = 44 nM; LC50 > 100 mu M) compared with arimidex (IC50 = 600 nM; LC50 > 200 mu M).

  DOI：

  10.1021/jm0508282
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 2-溴-1-(4-乙基苯基)乙酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 以65%的产率得到(4-ethylphenyl)(6-methoxybenzofuran-2-yl)methanone
  参考文献：
  名称：

  Potent CYP19 (Aromatase) 1-[(Benzofuran-2-yl)(phenylmethyl)pyridine, -imidazole, and -triazole Inhibitors:  Synthesis and Biological Evaluation

  摘要：

  The synthesis of a series of novel 1-[(benzofuran-2-yl)phenylmethyl]-pyridine, -imidazole, and -triazole derivatives is described. All the compounds were evaluated in vitro for inhibitory activity against aromatase (P450(AROM), CYP19), using human placental microsomes. The 6-methoxy- and 6-hydroxy-substituted benzofuran derivatives were shown to be potent CYP19 inhibitors (IC50 = 0.01-1.46 mu M) with activity greater than that observed for the unsubstituted parent compounds and inhibitory activity comparable with or greater than the reference compound arimidex (IC50 = 0.6 mu M). Six of the benzofuran derivatives were subjected to in vitro cytotoxicity assays, using rat liver hepatocytes with cytotoxicity determined from alteration in cell morphology and lactate dehydrogenase enzyme retention over a period of 24 h, and selectivity (CYP17, 17 beta-HSD types 1 and 3, CYP24, and CYP26) determination; negligible inhibitory activity was observed, suggesting a good selectivity for CYP19. The pyridine benzofuran 4a containing the 4-fluorophenyl group was the most promising (IC50 = 44 nM; LC50 > 100 mu M) compared with arimidex (IC50 = 600 nM; LC50 > 200 mu M).

  DOI：

  10.1021/jm0508282

文献信息

• Potent CYP19 (Aromatase) 1-[(Benzofuran-2-yl)(phenylmethyl)pyridine, -imidazole, and -triazole Inhibitors:  Synthesis and Biological Evaluation
  作者：Mohammed Reza Saberi、Tai Ky Vinh、Sook Wah Yee、B. J. Nathan Griffiths、Peter J. Evans、Claire Simons

  DOI：10.1021/jm0508282

  日期：2006.2.1

  The synthesis of a series of novel 1-[(benzofuran-2-yl)phenylmethyl]-pyridine, -imidazole, and -triazole derivatives is described. All the compounds were evaluated in vitro for inhibitory activity against aromatase (P450(AROM), CYP19), using human placental microsomes. The 6-methoxy- and 6-hydroxy-substituted benzofuran derivatives were shown to be potent CYP19 inhibitors (IC50 = 0.01-1.46 mu M) with activity greater than that observed for the unsubstituted parent compounds and inhibitory activity comparable with or greater than the reference compound arimidex (IC50 = 0.6 mu M). Six of the benzofuran derivatives were subjected to in vitro cytotoxicity assays, using rat liver hepatocytes with cytotoxicity determined from alteration in cell morphology and lactate dehydrogenase enzyme retention over a period of 24 h, and selectivity (CYP17, 17 beta-HSD types 1 and 3, CYP24, and CYP26) determination; negligible inhibitory activity was observed, suggesting a good selectivity for CYP19. The pyridine benzofuran 4a containing the 4-fluorophenyl group was the most promising (IC50 = 44 nM; LC50 > 100 mu M) compared with arimidex (IC50 = 600 nM; LC50 > 200 mu M).