adenosine 5'-(aminocarbonyl)phosphonate | 102831-55-0

• 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: adenosine 5'-(aminocarbonyl)phosphonate
• 英文别名: 9H-Purin-6-amine, 9-(5-O-((aminocarbonyl)hydroxyphosphinyl)-beta-D-ribofuranosyl)-；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-carbamoylphosphinic acid
• CAS: 102831-55-0
• 化学式: C₁₁H₁₅N₆O₇P
• 分子量: 374.25
• InChiKey: WFMFZCMDIMBWNC-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2',3'-(methoxymethylidene)adenosine 在 吡啶 、 ammonium hydroxide 、 甲酸 、 N,N'-二环己基碳二亚胺 作用下， 反应 11.5h， 生成 adenosine 5'-(aminocarbonyl)phosphonate
  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

• Synthesis and antiviral activity of certain nucleoside 5'-phosphonoformate derivatives
  作者：Morteza M. Vaghefi、Patricia A. McKernan、Roland K. Robins

  DOI：10.1021/jm00158a012

  日期：1986.8

  Adenosine 5'-(ethoxycarbonyl)phosphonate (4), guanosine 5'-(ethoxycarbonyl)phosphonate (5), 2'-deoxyadenosine 5'-(ethoxycarbonyl)phosphonate (18) and 2'-deoxyguanosine 5'-(ethoxycarbonyl)phosphonate (19) were synthesized by coupling of compound 3 with adenosine, guanosine, 2'-deoxyadenosine, and 2'-deoxyguanosine, respectively. Alkaline treatment of 4, 5, 18, and 19 gave the corresponding adenosine 5'-(h

  通过用亚硫酰氯氯化双（三甲基甲硅烷基）（乙氧羰基）膦酸酯来合成（乙氧羰基）膦二氯化物（3）。腺苷5'-（乙氧羰基）膦酸酯（4），鸟苷5'-（乙氧羰基）膦酸酯（5），2'-脱氧腺苷5'-（乙氧羰基）膦酸酯（18）和2'-脱氧鸟苷5'-（乙氧羰基）膦酸酯（19）是通过化合物3分别与腺苷，鸟苷，2'-脱氧腺苷和2'-脱氧鸟苷偶联而合成的。对4、5、18和19进行碱处理，得到相应的腺苷5'-（羟基羰基）膦酸酯（14），鸟苷5'-（羟基羰基）膦酸酯（15），2'-脱氧腺苷5'-（羟基羰基）膦酸酯（ 20），和2'-脱氧鸟苷5'-（羟基羰基）膦酸酯（21）。用甲醇氨处理4和5分别产生腺苷5'-（氨基羰基）膦酸酯（12）和鸟苷5'-（氨基羰基）膦酸酯（13）。核苷酸类似物20在体外测试的这一组核苷酸中表现出最有效的抗病毒活性，并且对疱疹病毒尤其是HSV-2最具活性。核苷酸类似物21具有较低但显着的针对H