N6-4-monomethoxytrityl-9-[2-(diethylphosphonylmethoxy)ethyl]adenine | 153235-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N6-4-monomethoxytrityl-9-[2-(diethylphosphonylmethoxy)ethyl]adenine
• 英文别名: N⁶-4-monomethoxytrityl-9-[2-(diethylphosphonylmethoxy)ethyl]adenine
• CAS: 153235-85-9
• 化学式: C₃₂H₃₆N₅O₅P
• 分子量: 601.642
• InChiKey: WOPDGLSKYCXBEN-UHFFFAOYSA-N

物化性质

• 沸点：
  733.9±70.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109.62
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N6-4-monomethoxytrityl-9-[2-(diethylphosphonylmethoxy)ethyl]adenine 在 吡啶 、 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.5h， 生成 N⁶-4-monomethoxytrityl-9-{2-[(3-methyl-cycloSal)phosphonylmethoxy]ethyl}adenine
  参考文献：
  名称：

  cycloSal-PMEA and cycloAmb-PMEA:  Potentially New Phosphonate Prodrugs Based on the cycloSal-Pronucleotide Approach

  摘要：

  Two new classes of lipophilic prodrugs of the antiviral active phosphonate 9-[2-phosphonomethoxyethyl] adenine (PMEA 1) have been prepared and were studied with regard to their hydrolysis properties and biological activity. A first series of compounds was prepared on the basis of the cycloSal nucleotide approach. Because of the surprisingly low hydrolysis stability of these cycloSal-PMEA derivatives, more stable derivatives have to be developed. Instead of using salicyl alcohol, in cycloAmb-PMEA derivatives 2-aminobenzyl alcohols were attached to PMEA 1. The latter compounds showed a considerably higher stability compared to the cycloSal counterparts. Stability studies revealed that all lipophilic prodrugs delivered PMEA selectively by chemical means. All compounds proved to be noninhibiting to acetyl- and butyryleholinesterase, and some of the phosphonate diesters were found to be more active against HIV compared to the parent PMEA.

  DOI：

  10.1021/jm050641a
• 作为产物：
  描述：

  [[2-(6-氨基-9H-嘌呤-9-基)乙氧基]甲基]膦酸二乙酯 、 4-甲氧基三苯基氯甲烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以89%的产率得到N6-4-monomethoxytrityl-9-[2-(diethylphosphonylmethoxy)ethyl]adenine
  参考文献：
  名称：

  cycloSal-PMEA and cycloAmb-PMEA:  Potentially New Phosphonate Prodrugs Based on the cycloSal-Pronucleotide Approach

  摘要：

  Two new classes of lipophilic prodrugs of the antiviral active phosphonate 9-[2-phosphonomethoxyethyl] adenine (PMEA 1) have been prepared and were studied with regard to their hydrolysis properties and biological activity. A first series of compounds was prepared on the basis of the cycloSal nucleotide approach. Because of the surprisingly low hydrolysis stability of these cycloSal-PMEA derivatives, more stable derivatives have to be developed. Instead of using salicyl alcohol, in cycloAmb-PMEA derivatives 2-aminobenzyl alcohols were attached to PMEA 1. The latter compounds showed a considerably higher stability compared to the cycloSal counterparts. Stability studies revealed that all lipophilic prodrugs delivered PMEA selectively by chemical means. All compounds proved to be noninhibiting to acetyl- and butyryleholinesterase, and some of the phosphonate diesters were found to be more active against HIV compared to the parent PMEA.

  DOI：

  10.1021/jm050641a