Synthesis and antiviral activity of 1,5- and 1,3-dialkyl-1,2,4-triazole C-nucleosides derived from 1-(chloroalkyl)-1-aza-2-azoniaallene salts.
Reactions of alpha,alpha'-dichloroazo compounds 2 with SbCl5 gave 1-(chloroalkyl)-1-aza-2-azoniaallene salts 3 as reactive intermediates. Cycloadditions of 3 with the ribofuranosyl cyanide 4 afforded the beta-D-ribofuranosyl-1,2,4-triazolium salts 5, which rearranged spontaneously to salts 6. Hydrolysis of 6 gave the 1,2,4-triazole C-nucleosides 7, which yielded the free nucleosides 8 after deblocking. Analogously, 12 was prepared from the cycloaddition of 4 with the alpha-chloroazo compound 10 in the presence of SbCl5. Deblocking of 12 with sodium methoxide afforded 13. Compounds 8a,b,e,f and 13 were tested against HIV-1, HIV-2, HSV-1 and HSV-2 and were found to be inactive.
al-Soud
Y A
YA
Department of Chemistry, Al al-Bayt University, Mafraq, Jordan.
al-Masoudi
W A
WA
el-Halawa
R A
RA
al-Masoudi
N
N
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D019380:Anti-HIV Agents; D009705:Nucleosides; D014230:Triazoles