(S)-2,6-diamino-N6,N6-diethyl-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine | 1305351-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (S)-2,6-diamino-N6,N6-diethyl-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine
• 英文别名: [(2S)-1-[2-amino-6-(diethylamino)purin-9-yl]-3-fluoropropan-2-yl]oxymethylphosphonic acid
• CAS: 1305351-91-0
• 化学式: C₁₃H₂₂FN₆O₄P
• 分子量: 376.328
• InChiKey: YUGPVYOFDUMEBM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (S)-2-amino-6-chloro-9-<2-<(diisopropylphosphono)methoxy>-3-fluoropropyl>purine 在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 生成 (S)-2,6-diamino-N6,N6-diethyl-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine
  参考文献：
  名称：

  Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines

  摘要：

  An efficient method for the synthesis of N-9-[3-fluoro-2-(phosphonomethoxy) propyl] (FPMP) derivatives of purine bases has been developed. Both (R)- and (S)-enantiomers of the N-6-substituted FPMP derivatives of adenine and 2,6-diaminopurine were prepared and their anti-human immunodeficiency virus (HIV) and anti-Moloney murine sarcoma virus (MSV) activity was evaluated. Whereas none of the 6-substituted FPMPA derivatives showed any antiviral activity, several FPMPDAP derivatives had a moderate antiretroviral activity. Moreover, the data obtained from the study of the substrate activity of the active derivatives towards N-6-methyl-AMP aminohydrolase support the notion that the studied N-6-substituted FPMPDAP derivatives act as prodrugs of the antiretroviral FPMPG analogues. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.050