Synthesis of 1,4-disubstituted mono and bis-triazolocarbo-acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine by Cu(I)-catalyzed click azide-alkyne cycloaddition.
A series of novel mono-1,2,3-triazole and bis-1,2,3-triazole acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine was prepared via copper(I)-catalyzed 1,3-dipolar cycloaddition of N-9 propargylpurine, N-1-propargylpyrimidines/as-triazine with the azido-pseudo-sugar 4-azidobutylacetate under solvent-free microwave conditions, followed by treatment with K(2)CO(3)/MeOH, or NH(3)/MeOH. All compounds studied in this work were screened for their antiviral activities [against human rhinovirus (HRV) and hepatitis C virus (HCV)] and antibacterial activities against a series of Gram positive and negative bacteria.
Laboratoire de Chimie Bioorganique et Macromoléculaire, Faculté des Sciences et Techniques-Guéliz, 40000, Marrakech, Maroc.
Jamal
J
Krim
Moha
M
Taourirte
Joachim W
JW
Engels
D000212:Acyclovir / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000480:Alkynes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001386:Azides / Q000737:chemistry*; D057930:Click Chemistry / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests
D000480:Alkynes; D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D001386:Azides; C039093:9-(4-hydroxybutyl)guanine; D003300:Copper; D000212:Acyclovir