title: [Synthesis of 6-benzyl-1-[(benzyloxy)methyl]-3-hydroxy-5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione].
abstract: OBJECTIVE
  To find the best synthesis method of 6-benzyl-1-[(benzyloxy)methyl]-3-hydroxy-5-(hydroxymethyl) pyrimidine-2,4(1H,3H)-dione e for observing the change of its biological activity after N-3 hydroxylation.
  
  
  METHODS
  After trying some N-hydroxylation methods, the target compound was successfully synthesized via one-pot oxidizing process by sodium hydride (NaH) and 3-chloroperbenzoic acid(m-CPBA); the anti-HIV reverse transcriptase (RT) activity and integrase (IN) activity of the target compound was assayed via enzyme-linked immunesorbent assay (ELISA) and phosphorylation of DNA package method.
  
  
  RESULTS
  The target compound could be obtained through the improved m-CPBA oxidative method by only one step, and the yield of the reaction could reach 60%-70%. And the structure of this compound was identified by 1H NMR, 13C NMR and MS; The activity result showed it added the anti-HIV IN activity after N-3 hydroxylation as well as retained the anti-HIV RT activity.
  
  
  CONCLUSIONS
  The improved m-CPBA oxidative method is a convenient and efficient way to prepare the compound 6-benzyl-1-[(benzyloxy)methyl]-3-hydroxy-5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione e which has both anti-HIV RT and IN activity.
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Xiao-wan
authors.initials: XW
authors.lastname: Tang
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Liang
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Jian-xiong
authors.initials: JX
authors.lastname: Zhao
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Guo
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Zhi-li
authors.initials: ZL
authors.lastname: Zhang
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Chao
authors.initials: C
authors.lastname: Tian
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China.
authors.forename: Xiao-wei
authors.initials: XW
authors.lastname: Wang
authors.affiliation: Department of Chemical Biology, Peking University School of Pharmaceutical Sciences, Beijing 100191, China;Department of State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China.
authors.forename: Jun-yi
authors.initials: JY
authors.lastname: Liu
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis*; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D015497:HIV-1 / Q000187:drug effects*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*
chemical_list: D019380:Anti-HIV Agents; D019428:HIV Integrase Inhibitors; D011741:Pyrimidine Nucleosides; D054303:HIV Reverse Transcriptase