hexadecyl 3'-deoxy-5'-adenosinyl phosphate sodium salt | 144744-79-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: hexadecyl 3'-deoxy-5'-adenosinyl phosphate sodium salt
• CAS: 144744-79-6
• 化学式: C₂₆H₄₅N₅O₆P*Na
• 分子量: 577.637
• InChiKey: XGMCQLHVYQAVDK-LNWXEOQTSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  39.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  157.67
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 在 4-二甲氨基吡啶 四氮唑 、 碘 、 sodium methylate 、 三乙胺 、 N,N-二异丙基乙胺 、 苯磺酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.75h， 生成 hexadecyl 3'-deoxy-5'-adenosinyl phosphate sodium salt
  参考文献：
  名称：

  O-Alkyl-5',5'-dinucleoside phosphates as prodrugs of 3'-azidothymidine and cordycepin

  摘要：

  The syntheses of two O-alkyl-5',5'-dinucleoside phosphotriesters 2a and 2b as combined prodrugs of the antiviral drug AZT (1) and the antibiotic agent cordycepin (3) are described. 2a,b were obtained as a 1:1 diastereomeric mixture. The absolute configuration of the isolated diastereomers was determined by NOE NMR experiments and correlated with the migration characteristics on silica gel as well as the P-31-NMR chemical shift. The conformational features of 2b(R) and 2b(S) were determined m deuteriated dodecylphosphocholine micelles in aqueous solution using 2D-NOESY spectra and shown to be dependent on the configuration at phosphorus. Additionally, all new compounds were tested for their antiviral activities in HIV-1-infected CEM C113 and H9 cell systems. Although all compounds were able to significantly inhibit the HIV-1-induced cytopathogenic effect, only the phosphodiester 12 gave a selectivity index (SI(RT) = 2000) comparable to the reference compound AZT (1) (SI(RT) = 3000).

  DOI：

  10.1021/jo00052a053