2-<(2-naphthalenylmethyl)thio>-6-(trifluoromethyl)-4-pyrimidinol | 214417-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<(2-naphthalenylmethyl)thio>-6-(trifluoromethyl)-4-pyrimidinol
• 英文别名: 2-(naphthalen-2-ylmethylsulfanyl)-4-(trifluoromethyl)-1H-pyrimidin-6-one
• CAS: 214417-55-7
• 化学式: C₁₆H₁₁F₃N₂OS
• 分子量: 336.337
• InChiKey: FWHVUPSOVVZDCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<(2-naphthalenylmethyl)thio>-6-(trifluoromethyl)-4-pyrimidinol 在 三氯氧磷 作用下， 反应 2.0h， 以58%的产率得到4-chloro-2-<(2-naphthalenylmethyl)thio>-6-(trifluoromethyl)pyrimidine
  参考文献：
  名称：

  Pyrimidine Thioethers:  A Novel Class of HIV-1 Reverse Transcriptase Inhibitors with Activity Against BHAP-Resistant HIV

  摘要：

  A series of pyrimidine thioethers was synthesized and evaluated for inhibitory properties against wild-type HIV-1 reverse transcriptase (RT) and an RT carrying the resistance-conferring mutation P236L. Modifications of both the pyrimidine and the functionality attached through the thioether yielded several analogues, which demonstrated activity against both enzyme types, with IC50 values as low as 190 nM against wild-type and 66 nM against P236L RT. Evaluation of a select number of pyrimidine thioethers in cell culture showed that these compounds have excellent activity against HIV-1(IIIB)-WT and retain good activity against a laboratory-derived HIV-1(MF) delavirdine-resistant variant.

  DOI：

  10.1021/jm9800806
• 作为产物：
  描述：

  4-羟基-6-(三氟甲基)嘧啶-2-硫醇 、 2-溴甲基萘 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-<(2-naphthalenylmethyl)thio>-6-(trifluoromethyl)-4-pyrimidinol
  参考文献：
  名称：

  Pyrimidine Thioethers:  A Novel Class of HIV-1 Reverse Transcriptase Inhibitors with Activity Against BHAP-Resistant HIV

  摘要：

  A series of pyrimidine thioethers was synthesized and evaluated for inhibitory properties against wild-type HIV-1 reverse transcriptase (RT) and an RT carrying the resistance-conferring mutation P236L. Modifications of both the pyrimidine and the functionality attached through the thioether yielded several analogues, which demonstrated activity against both enzyme types, with IC50 values as low as 190 nM against wild-type and 66 nM against P236L RT. Evaluation of a select number of pyrimidine thioethers in cell culture showed that these compounds have excellent activity against HIV-1(IIIB)-WT and retain good activity against a laboratory-derived HIV-1(MF) delavirdine-resistant variant.

  DOI：

  10.1021/jm9800806

文献信息

• Pyrimidine Thioethers:  A Novel Class of HIV-1 Reverse Transcriptase Inhibitors with Activity Against BHAP-Resistant HIV
  作者：Richard A. Nugent、Stephen T. Schlachter、Michael J. Murphy、Gary J. Cleek、Toni J. Poel、Donn G. Wishka、David R. Graber、Yoshihiko Yagi、Barbara J. Keiser、Robert A. Olmsted、Laurie A. Kopta、Steven M. Swaney、Susan M. Poppe、Joel Morris、W. Gary Tarpley、Richard C. Thomas

  DOI：10.1021/jm9800806

  日期：1998.9.1

  A series of pyrimidine thioethers was synthesized and evaluated for inhibitory properties against wild-type HIV-1 reverse transcriptase (RT) and an RT carrying the resistance-conferring mutation P236L. Modifications of both the pyrimidine and the functionality attached through the thioether yielded several analogues, which demonstrated activity against both enzyme types, with IC50 values as low as 190 nM against wild-type and 66 nM against P236L RT. Evaluation of a select number of pyrimidine thioethers in cell culture showed that these compounds have excellent activity against HIV-1(IIIB)-WT and retain good activity against a laboratory-derived HIV-1(MF) delavirdine-resistant variant.