6-(5-fluoro-2-hydroxyphenoxy)-2-naphthonitrile | 1322035-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(5-fluoro-2-hydroxyphenoxy)-2-naphthonitrile
• CAS: 1322035-96-0
• 化学式: C₁₇H₁₀FNO₂
• 分子量: 279.27
• InChiKey: USOPGXAJZNAWMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.25
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[4-(aminosulfonyl)-2-methylphenyl]-2-bromoacetamide 、 6-(5-fluoro-2-hydroxyphenoxy)-2-naphthonitrile 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以61%的产率得到2-(4-fluoro-2-(6-cyano-2-naphthyloxy)phenoxy)-N-(2-methyl-4-sulfamoylphenyl)acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of naphthyl phenyl ethers (NPEs) as novel nonnucleoside HIV-1 reverse transcriptase inhibitors

  摘要：

  A novel series of naphthyl phenyl ether analogues (NPEs) have been synthesized and evaluated for their in vitro activities against HIV in C8166 cells. Most of the compounds exhibited moderate to excellent anti-HIV activities. Among them the most active compound 12o showed excellent activities against wild-type HIV-1 with an EC(50) value of 4.60 nM, along with moderate activities against the double mutant strain HIV-1(IIIB) A17 (K103N+Y181C) and HIV-2 strain ROD with an EC(50) value of 0.82 and 4.40 mu M, respectively. Preliminary structure-activity relationship (SAR) among the newly synthesized NPEs was also investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.060
• 作为产物：
  描述：

  2-溴-4-氟苯酚 在 potassium phosphate 、 copper(l) iodide 、 三溴化硼 、 potassium carbonate 、 (E)-1-(2-pyridinyl)methylene-2-phenylhydrazine 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.5h， 生成 6-(5-fluoro-2-hydroxyphenoxy)-2-naphthonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of naphthyl phenyl ethers (NPEs) as novel nonnucleoside HIV-1 reverse transcriptase inhibitors

  摘要：

  A novel series of naphthyl phenyl ether analogues (NPEs) have been synthesized and evaluated for their in vitro activities against HIV in C8166 cells. Most of the compounds exhibited moderate to excellent anti-HIV activities. Among them the most active compound 12o showed excellent activities against wild-type HIV-1 with an EC(50) value of 4.60 nM, along with moderate activities against the double mutant strain HIV-1(IIIB) A17 (K103N+Y181C) and HIV-2 strain ROD with an EC(50) value of 0.82 and 4.40 mu M, respectively. Preliminary structure-activity relationship (SAR) among the newly synthesized NPEs was also investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.060