6-(pyridin-4-yl)-1-naphthol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(pyridin-4-yl)-1-naphthol
• 英文别名: 6-Pyridin-4-ylnaphthalen-1-ol
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: SLFBZDWSFUQAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(pyridin-4-yl)-1-naphthol 、 Dimethylammonium sulphite 在 甲胺 作用下， 以 水 为溶剂， 生成 Methyl-(6-pyridin-4-yl-naphthalen-1-yl)-amine
  参考文献：
  名称：

  异喹啉衍生物与吡啶盐反应生成 4-萘基吡啶

  摘要：

  在异喹啉盐与 4-甲基吡啶鎓盐的反应中，通过异喹啉双环系统的分子间转化（包括吡啶鎓盐的甲基），将 2-萘基残基区域特异性地引入吡啶环的 4 位。该反应在亚硫酸甲铵的作用下在水性介质中加热发生。该方法不仅为异喹啉盐提供环转化，甚至为未取代的异喹啉提供环转化。

  DOI：

  10.1023/b:rucb.0000037861.00184.82
• 作为产物：
  描述：

  6-羟基-1-四氢萘酮 在 吡啶 、 盐酸 、 四(三苯基膦)钯 、 溴 、 lithium carbonate 、 caesium carbonate 、 lithium bromide 作用下， 以 四氯化碳 、 乙二醇二甲醚 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-(pyridin-4-yl)-1-naphthol
  参考文献：
  名称：

  17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold

  摘要：

  17 beta-Hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) catalyses the conversion of active 17 beta-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17 beta-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17 beta-HSD2 inhibitors displaying high activity and good selectivity toward 17 beta-HSD1, ER alpha and ER beta. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.013

文献信息

• 17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold
  作者：Marie Wetzel、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2010.12.013

  日期：2011.1

  17 beta-Hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) catalyses the conversion of active 17 beta-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17 beta-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17 beta-HSD2 inhibitors displaying high activity and good selectivity toward 17 beta-HSD1, ER alpha and ER beta. (C) 2010 Elsevier Ltd. All rights reserved.
• Reactions of isoquinoline derivatives with pyridinium salts yielding 4-naphthylpyridines
  作者：S. P. Gromov、M. V. Fomina

  DOI：10.1023/b:rucb.0000037861.00184.82

  日期：2004.4

  ring occurs in the reactions of isoquinolinium salts with 4-methylpyridinium salts through the intermolecular transformation of the isoquinoline bicyclic system involving the methyl group of the pyridinium salt. The reaction occurs under the action of methylammonium sulfite in an aqueous medium on heating. This method provides ring transformation not only for isoquinolinium salts but even for unsubstituted

  在异喹啉盐与 4-甲基吡啶鎓盐的反应中，通过异喹啉双环系统的分子间转化（包括吡啶鎓盐的甲基），将 2-萘基残基区域特异性地引入吡啶环的 4 位。该反应在亚硫酸甲铵的作用下在水性介质中加热发生。该方法不仅为异喹啉盐提供环转化，甚至为未取代的异喹啉提供环转化。