Synthesis of 5'-N-(alpha-amino-beta-mercaptoacyl)amino-5'-deoxynucleosides as potential antiviral compounds.
5'-N-(alpha-Amino-beta-mercaptoacyl)amino-5'-deoxynucleosides have been synthesized by coupling of N-formylthiazolidines derived from D- and L-penicillamine, and D- and L-cysteine to 5'-amino-5'-deoxynucleosides using the DCC/HOSu method, followed by deprotection in N HCl in MeOH under argon. Although these compounds were designed as potential anti-HIV-1 agents, none of them showed anti-HIV-1 activity in MT-4 cells or antiviral effect against some other viruses, at concentrations below the cytotoxicity threshold.
Herranz
R
R
Instituto de Química Médica, C.S.I.C., Madrid, Spain.
Castro-Pichel
J
J
García-López
M T
MT
Pérez
C
C
Balzarini
J
J
De Clercq
E
E
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002478:Cells, Cultured; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D003853:Deoxyribonucleosides; D013438:Sulfhydryl Compounds