3-(pyridin-3-yl)-2-naphthol | 1054314-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(pyridin-3-yl)-2-naphthol
• 英文别名: 3-(3-hydroxynaphthalen-2-yl)pyridine；3-Pyridin-3-ylnaphthalen-2-ol
• CAS: 1054314-89-4
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: YCBKAUDDUSVNRL-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：

  3-(pyridin-3-yl)-2-naphthol 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-methoxyphenylthio)-3-(pyridin-3-yl)-2-naphthol
  参考文献：
  名称：

  Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols

  摘要：

  1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.111
• 作为产物：
  描述：

  3-(3-methoxynaphthalen-2-yl)-pyridine 在 水 、 氢溴酸 作用下， 反应 18.0h， 以65%的产率得到3-(pyridin-3-yl)-2-naphthol
  参考文献：
  名称：

  Novel Aldosterone Synthase Inhibitors with Extended Carbocyclic Skeleton by a Combined Ligand-Based and Structure-Based Drug Design Approach

  摘要：

  Pharmacophore modeling of a series of aldosterone synthase (CYP11B2) inhibitors triggered the design of compounds 11 and 12 by extending a previously established naphthalene molecular scaffold (e.g., present in molecules 1 and 2) via introduction of a phenyl or benzyl residue in 3-position. These additional aromatic moieties have been hypothesized to fit into the newly identified hydrophobic pharmacophore feature HY3. Subsequent docking studies in our refined CYP11B2 protein model have been performed prior to synthesis to estimate the inhibitory properties of the proposed molecules. While phenyl-substituted compound 11 (IC50 > 500 nM) did not dock under the given pharmacophore constraint (i.e., the Fe(heme)-N(ligand) interaction), benzyl-substituted compound 12 (IC50 = 154 nM) was found to exploit a previously unexplored subpocket of the inhibitor binding site. By structural optimization based on the pharmacophore hypothesis, 25 novel compounds were synthesized, among them highly potent CYP11B2 inhibitors (e.g., 17, IC50 = 2.7 nM) with pronounced selectivity toward the most important steroidogenic and hepatic CYP enzymes.

  DOI：

  10.1021/jm800683c