5-[6-(3-methoxyphenyl)-1-naphthyl]pyrimidine | 1262388-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[6-(3-methoxyphenyl)-1-naphthyl]pyrimidine
• 英文别名: 5-[6-(3-Methoxyphenyl)naphthalen-1-yl]pyrimidine
• CAS: 1262388-35-1
• 化学式: C₂₁H₁₆N₂O
• 分子量: 312.371
• InChiKey: UTLCLIVJEMDVGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[6-(3-methoxyphenyl)-1-naphthyl]pyrimidine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到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 吡啶 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 4-异丙基甲苯 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 5-[6-(3-methoxyphenyl)-1-naphthyl]pyrimidine
  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