(6-methoxybenzofuran-2-yl)(4-nitrophenyl)methanol | 878196-30-6

• 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: (6-methoxybenzofuran-2-yl)(4-nitrophenyl)methanol
• 英文别名: (6-Methoxy-1-benzofuran-2-yl)-(4-nitrophenyl)methanol
• CAS: 878196-30-6
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: XWGZCNFIKVGWTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6-methoxybenzofuran-2-yl)(4-nitrophenyl)methanol 、 1H-1,2,4-三唑 在 氯化亚砜 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 121.0h， 生成 1-[(6-methoxybenzofuran-2-yl)-(4-nitrophenyl)-methyl]-1H-1,2,4-triazole
  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 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 (6-methoxybenzofuran-2-yl)(4-nitrophenyl)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

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).