Guanosine, 2a(2)-deoxy-, 3a(2)-benzoate | 80508-83-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Guanosine, 2a(2)-deoxy-, 3a(2)-benzoate
• 英文别名: [(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 80508-83-4
• 化学式: C₁₇H₁₇N₅O₅
• 分子量: 371.352
• InChiKey: XWPWLQJIBHPWMY-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  145.35
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Guanosine, 2a(2)-deoxy-, 3a(2)-benzoate 在 吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 反应 10.0h， 生成 2'-desoxyguanosine methylphosphonate
  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

• KAMOR, P. C. J.;ROELEN, H. G. P. E.;ELOT, H. VAN DEN;MAROL, G. A. VAN DER+, TETRAHEDRON LETT., 30,(1989) N8, C. 6757-6760
  作者：KAMOR, P. C. J.、ROELEN, H. G. P. E.、ELOT, H. VAN DEN、MAROL, G. A. VAN DER+

  DOI：——

  日期：——