1-bromo-6-(2-methoxyphenyl)-2-naphthol | 1262388-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-6-(2-methoxyphenyl)-2-naphthol
• 英文别名: 1-Bromo-6-(2-methoxyphenyl)naphthalen-2-ol
• CAS: 1262388-38-4
• 化学式: C₁₇H₁₃BrO₂
• 分子量: 329.193
• InChiKey: MGENZMBNRWBKCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-6-(2-methoxyphenyl)-2-naphthol 在 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， -78.0~150.0 ℃ 、1.5 MPa 条件下， 反应 0.42h， 生成 1-pyrimidin-5-yl-6-(2-hydroxyphenyl)-2-naphthol
  参考文献：
  名称：

  New Drug-Like Hydroxyphenylnaphthol Steroidomimetics As Potent and Selective 17β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors for the Treatment of Estrogen-Dependent Diseases

  摘要：

  Inhibition of 17 beta-hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) is a novel and attractive approach to reduce the local levels of the active estrogen 17 beta-estradiol in patients with estrogen-dependent diseases like breast cancer or endometriosis. With the aim of optimizing the biological profile of 17 beta-HSD1 inhibitors from the hydroxyphenylnaphthol class, structural optimizations were performed at the 1-position of the naphthalene by introduction of different heteroaromatic rings as well as substituted phenyl groups. In the latter class of compounds, which were synthesized applying Suzuki-cross coupling, the 3-methane-sulfonamide 15 turned out to be a highly potent 17 beta-HSD1 inhibitor (IC50 = 15 nM in a cell-free assay). It was also very active in the cellular assay (T47D cells, IC50 = 71 nM) and selective toward 17 beta-HSD2 and the estrogen receptors alpha and beta. It showed a good membrane permeation and metabolic stability and was orally available in the rat.

  DOI：

  10.1021/jm1009082
• 作为产物：
  描述：

  6-(2-methoxyphenyl)naphthalen-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以54%的产率得到1-bromo-6-(2-methoxyphenyl)-2-naphthol
  参考文献：
  名称：

  New Drug-Like Hydroxyphenylnaphthol Steroidomimetics As Potent and Selective 17β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors for the Treatment of Estrogen-Dependent Diseases

  摘要：

  Inhibition of 17 beta-hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) is a novel and attractive approach to reduce the local levels of the active estrogen 17 beta-estradiol in patients with estrogen-dependent diseases like breast cancer or endometriosis. With the aim of optimizing the biological profile of 17 beta-HSD1 inhibitors from the hydroxyphenylnaphthol class, structural optimizations were performed at the 1-position of the naphthalene by introduction of different heteroaromatic rings as well as substituted phenyl groups. In the latter class of compounds, which were synthesized applying Suzuki-cross coupling, the 3-methane-sulfonamide 15 turned out to be a highly potent 17 beta-HSD1 inhibitor (IC50 = 15 nM in a cell-free assay). It was also very active in the cellular assay (T47D cells, IC50 = 71 nM) and selective toward 17 beta-HSD2 and the estrogen receptors alpha and beta. It showed a good membrane permeation and metabolic stability and was orally available in the rat.

  DOI：

  10.1021/jm1009082