6-(3-methoxyphenyl)-1-naphthol | 1262388-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(3-methoxyphenyl)-1-naphthol
• CAS: 1262388-33-9
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: RFCRTQRVBRGKRY-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  6-(3-methoxyphenyl)-1-naphthol 在 吡啶 、 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 3-[5-(pyrimidin-5-yl)-2-naphthyl]phenol
  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-(3-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 在 palladium 10% on activated carbon 作用下， 以 4-异丙基甲苯 为溶剂， 以100%的产率得到6-(3-methoxyphenyl)-1-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