4-amino-6-chloro-2-[(piperon-5-ylmethyl)thio]pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-amino-6-chloro-2-[(piperon-5-ylmethyl)thio]pyrimidine
• 英文别名: 2-(1,3-Benzodioxol-5-ylmethylsulfanyl)-6-chloro-pyrimidin-4-amine；2-(1,3-benzodioxol-5-ylmethylsulfanyl)-6-chloropyrimidin-4-amine
• 化学式: C₁₂H₁₀ClN₃O₂S
• 分子量: 295.749
• InChiKey: BETDGJUYCZKGGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒基氯 、 4-氨基-6-氯-2(1H)-嘧啶硫酮 生成 4-amino-6-chloro-2-[(piperon-5-ylmethyl)thio]pyrimidine
  参考文献：
  名称：

  Pyrimidine-thioalkyl and alkylether compounds

  摘要：

  该发明涉及Formula I的嘧啶硫代烷基和烷基醚化合物，以及Formula IA的嘧啶硫代烷基和烷基醚化合物，即Formula I中R4选自-H或-NR15R16的基团，其中R15为-H，R16为-H，C1-C6烷基，-NH2或R15和R16一起与-N形成1-吡咯啉基、1-吗啉基或1-哌啶基；以及R6选自-H或卤素（优选-Cl）的基团，总体规定是R4和R6不能同时为-H；Formula IA的化合物在治疗HIV阳性个体中是有用的。

  公开号：

  EP1247804A1

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.
• Pyrimidine-thioalkyl and alkylether compounds
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1247804A1

  公开（公告）日：2002-10-09

  The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula I and pyrimidine-thioalkyl and alkylethers of Formula IA, namely the compounds of Formula I where R4 is selected from the group consisting of -H or -NR15R16 where R15 is -H and R16 is -H, C1-C6 alkyl, -NH2 or R15 and R16 taken together with the -N form 1-pyrrolidino, 1-morpholino or 1-piperidino; and R6 is selected from the group consisting of -H, or halo (preferably -Cl); with the overall provisio that R4 and R6 are not both -H; The compounds of Formula IA are useful in the treatment of individuals who are HIV positive.

  该发明涉及Formula I的嘧啶硫代烷基和烷基醚化合物，以及Formula IA的嘧啶硫代烷基和烷基醚化合物，即Formula I中R4选自-H或-NR15R16的基团，其中R15为-H，R16为-H，C1-C6烷基，-NH2或R15和R16一起与-N形成1-吡咯啉基、1-吗啉基或1-哌啶基；以及R6选自-H或卤素（优选-Cl）的基团，总体规定是R4和R6不能同时为-H；Formula IA的化合物在治疗HIV阳性个体中是有用的。