Phosphoric acid mono-[(2S,4S)-4-(8-amino-imidazo[4,5-g]quinazolin-3-yl)-tetrahydro-furan-2-ylmethyl] ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: Phosphoric acid mono-[(2S,4S)-4-(8-amino-imidazo[4,5-g]quinazolin-3-yl)-tetrahydro-furan-2-ylmethyl] ester
• 英文别名: [(2S,4S)-4-(8-aminoimidazo[4,5-g]quinazolin-3-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate；[(2S,4S)-4-(8-aminoimidazo[4,5-g]quinazolin-3-yl)oxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₁₄H₁₆N₅O₅P
• 分子量: 365.285
• InChiKey: DLAKXITWKKRIRJ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  8-(methylthio)-1H-imidazo<4,5-g>quinazoline 在 18-冠醚-6 、 磷酸三乙酯 、 氨 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 Phosphoric acid mono-[(2S,4S)-4-(8-amino-imidazo[4,5-g]quinazolin-3-yl)-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  Inhibition of HIV integrase by novel nucleotides bearing tricyclic bases

  摘要：

  5'-Monophosphates of several novel dideoxynucleosides bearing tricyclic nucleobases were synthesized. Both linear and angular ring-extended analogs of isomeric dideoxyadenosine 5'-monophosphate were discovered to have moderate to good inhibition of the viral-encoded enzyme, HIV integrase. The results suggest that the nucleotide binding site of HIV integrase can accommodate major modifications in the nucleobase, which is in stark contrast to the nucleotide binding site on HIV reverse transcriptase, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00327-8

文献信息

• Synthesis of New Dideoxynucleosides Bearing Ring-Extended Nucleobases
  作者：Jianzhong Zhang、Vasu Nair

  DOI：10.1080/07328319708006139

  日期：1997.7

  New dideoxynucleosides where the nucleobase is lin-benzoadenine is reported. The key target compound, (S, S)-isodideoxybenzoadenosine, is stable with respect to hydrolytic cleavage of the glycosyl bond and it is a poor substrate for adenosine deaminase. Its monophosphate is not a substrate for AMP deaminase.
• Inhibition of HIV integrase by novel nucleotides bearing tricyclic bases
  作者：Jianzhong Zhang、Nouri Neamati、Yves Pommier、Vasu Nair

  DOI：10.1016/s0960-894x(98)00327-8

  日期：1998.7

  5'-Monophosphates of several novel dideoxynucleosides bearing tricyclic nucleobases were synthesized. Both linear and angular ring-extended analogs of isomeric dideoxyadenosine 5'-monophosphate were discovered to have moderate to good inhibition of the viral-encoded enzyme, HIV integrase. The results suggest that the nucleotide binding site of HIV integrase can accommodate major modifications in the nucleobase, which is in stark contrast to the nucleotide binding site on HIV reverse transcriptase, (C) 1998 Elsevier Science Ltd. All rights reserved.