6-hydroxy-2-(2-naphthylmethyl)thio-4-pyrimidine carboxaldehyde oxime | 185219-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-hydroxy-2-(2-naphthylmethyl)thio-4-pyrimidine carboxaldehyde oxime
• 英文别名: 4-(hydroxyiminomethyl)-2-(naphthalen-2-ylmethylsulfanyl)-1H-pyrimidin-6-one
• CAS: 185219-80-1
• 化学式: C₁₆H₁₃N₃O₂S
• 分子量: 311.364
• InChiKey: VGCYENIYHSOEES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2-(2-naphthylmethyl)thio-4-pyrimidine carboxaldehyde oxime 在 三氯氧磷 作用下， 生成 6-chloro-2-<(2-naphthalenylmethyl)thio>-4-pyrimidinecarbonitrile
  参考文献：
  名称：

  Alpha-substituted pyrimidine-thioalkyl and alkylether compounds as

  摘要：

  该发明涉及式(I)的嘧啶-硫代烷基和烷基醚化合物，以及式(IA)的嘧啶-硫代烷基和烷基醚化合物，即式(I)中R.sub.4选自--H或--NR.sub.15 R.sub.16组，其中R.sub.15为--H且R.sub.16为--H、C.sub.1-C.sub.6烷基、NH.sub.2或R.sub.15和R.sub.16连同--N形成1-吡咯烷基、1-吗啉基或1-哌啶基；以及R.sub.6选自--H或卤素（优选--Cl）的化合物组，总的限制条件是R.sub.4和R.sub.6不能同时为--H。式(IA)的化合物在治疗HIV阳性个体中具有抑制病毒逆转录酶的作用。

  公开号：

  US06043248A1

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.