6-(2,6-difluoro-4-hydroxyphenyl)-1-naphthol | 1340482-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(2,6-difluoro-4-hydroxyphenyl)-1-naphthol
• 英文别名: 6-(2,6-Difluoro-4-hydroxyphenyl)naphthalen-1-ol
• CAS: 1340482-20-3
• 化学式: C₁₆H₁₀F₂O₂
• 分子量: 272.251
• InChiKey: XZEXCTYZQJASQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-hydroxy-2-naphthyl trifluoromethanesulfonate 、 2,5-二氟-4-羟基苯基硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 150.0 ℃ 、1.5 MPa 条件下， 反应 0.42h， 以47%的产率得到6-(2,6-difluoro-4-hydroxyphenyl)-1-naphthol
  参考文献：
  名称：

  Introduction of an Electron Withdrawing Group on the Hydroxyphenylnaphthol Scaffold Improves the Potency of 17β-Hydroxysteroid Dehydrogenase Type 2 (17β-HSD2) Inhibitors

  摘要：

  Estrogen deficiency in postmenopausal women or elderly men is often associated with the skeletal disease osteoporosis. The supplementation of estradiol (E2) in osteoporotic patients is known to prevent bone fracture but cannot be administered because of adverse effect. As 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) oxidizes E2 to its inactive form estrone (E1) and has been found in osteoblastic cells, it is an attractive target for the treatment of osteoporosis. Twenty-one novel, naphthalene-derived compounds have been synthesized and evaluated for their 17 beta-HSD2 inhibition and their selectivity toward 17 beta-HSD1 and the estrogen receptors (ERs) alpha and beta. Compound 19 turned out to be the most potent and selective inhibitor of 17 beta-HSD2 in cell-free assays and had a very good cellular activity in MDA-MB-231 cells, expressing naturally 17 beta-HSD2. It also showed marked inhibition of the E1-formation by the rat and mouse orthologous enzymes and strong inhibition of monkey 17 beta-HSD2. It is thus an appropriate candidate to be further evaluated in a disease-oriented model.

  DOI：

  10.1021/jm2008453

文献信息

• Introduction of an Electron Withdrawing Group on the Hydroxyphenylnaphthol Scaffold Improves the Potency of 17β-Hydroxysteroid Dehydrogenase Type 2 (17β-HSD2) Inhibitors
  作者：Marie Wetzel、Sandrine Marchais-Oberwinkler、Enrico Perspicace、Gabriele Möller、Jerzy Adamski、Rolf W. Hartmann

  DOI：10.1021/jm2008453

  日期：2011.11.10

  Estrogen deficiency in postmenopausal women or elderly men is often associated with the skeletal disease osteoporosis. The supplementation of estradiol (E2) in osteoporotic patients is known to prevent bone fracture but cannot be administered because of adverse effect. As 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) oxidizes E2 to its inactive form estrone (E1) and has been found in osteoblastic cells, it is an attractive target for the treatment of osteoporosis. Twenty-one novel, naphthalene-derived compounds have been synthesized and evaluated for their 17 beta-HSD2 inhibition and their selectivity toward 17 beta-HSD1 and the estrogen receptors (ERs) alpha and beta. Compound 19 turned out to be the most potent and selective inhibitor of 17 beta-HSD2 in cell-free assays and had a very good cellular activity in MDA-MB-231 cells, expressing naturally 17 beta-HSD2. It also showed marked inhibition of the E1-formation by the rat and mouse orthologous enzymes and strong inhibition of monkey 17 beta-HSD2. It is thus an appropriate candidate to be further evaluated in a disease-oriented model.