Synthesis and Activity Against HBV of Novel Tetra-Seconucleoside Analogues of Dyphlline Having the Acyclic Chains of ACV and HBG.

Selective alkylation of dyphylline (1) with (2-acetoxyethoxy)methyl bromide (2a) or 4-acetoxybutyl bromide (2b) afforded 3'-O-[(acetoxyethoxy)methyl]dyphylline (3a) and 3'-O-(4-acetoxybutyl)-dyphylline (3b), respectively. A trans esterification process rather than alkylation of the dihydroxy-propyl side chain in 1 had taken place during the reaction with 2-p-toluoyloxy)ethyl chloride (5) to afford the respective 3'-toluoyloxy derivative 7 and not the anticipated 3'-O-[(p-toluoyloxy)ethyl]-dyphylline (6). Deacylation of 3a,b and 7 afforded 4a,b and 1, respectively. Viral screening of selected compounds against HBV has been investigated.


Nucleosides Nucleotides Nucleic Acids. 2008;27(3):309-17

Ashry el SH, Awad LF, Rashed N, Abdelrahman A, Rasheed HA.
Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt.