acetoxymethylphosphonic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: acetoxymethylphosphonic acid
• 英文别名: acetyloxymethylphosphonic acid
• 化学式: C₃H₇O₅P
• 分子量: 154.059
• InChiKey: HXDAXZMEUNYDDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-O-acetylthymidine 、 acetoxymethylphosphonic acid 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 10.0h， 生成
  参考文献：
  名称：

  5′-Phosphonates of Ribonucleosides and 2′-Deoxyribonucleosides: Synthesis and Antiviral Activity

  摘要：

  5'-Phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-O-acylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonylphosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by action of ammonia in methanol or aqueous ammonia. 5'-Hydrogenphosphonothioates of thymidine and 3'-deoxythymidine were obtained by reaction of phosphinic acid in the presence of pivaloyl chloride with 3'-O-acetylthymidine or 3'-deoxythymidine, respectively, followed by addition of powedered sulfur. 5'-O-methylenephosphonates of thymidine and 2'-deoxyadenosine were prepared by intramolecular reaction of corresponding 3'-O-iodomethylphosphonates under basic conditions. All compounds were tested for inhibition of several viruses, including HSV-2 and CMV, but showed no activity. A few compounds insignificantly inhibited HIV-1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized anti-HIV action of 3'-azido-3'-deoxythymidine (AZT) and it indirectly showed that even some nucleoside 5'-phosphonates could be partly hydrolyzed in cell culture to corresponding nucleosides.

  DOI：

  10.1080/07328319308018558

文献信息

• New derivatives of alkyl-and aminocarbonylphosphonic acids containing 3′-azido-3′-deoxythymidine
  作者：M. V. Jasko、A. V. Shipitsyn、A. L. Khandazhinskaya、E. A. Shirokova、P. N. Sol’yev、O. A. Plyasunova、A. G. Pokrovskii

  DOI：10.1134/s1068162006060069

  日期：2006.12

  New 5′-phosphonates of 3′-azido-3′-deoxythymidine were synthesized and shown to be low-toxic and markedly active in MT-4 cell cultures infected with HIV-1.

  合成了新的 3'-叠氮基-3'-脱氧胸苷的 5'-膦酸酯，在感染 HIV-1 的 MT-4 细胞培养物中显示出低毒和显着活性。