Synthesis of 3′‐Deoxy‐3′‐[4‐(pyrimidin‐1‐yl)methyl‐1,2,3‐triazol‐1‐yl]thymidine via 1,3‐Dipolar Cycloaddition.

Abstract

Synthesis of 3'-Deoxy-3'-[4-(pyrimidin-1-yl)methyl-1,2,3-triazol-1-yl]thymidinevia 1,3-Dipolar Cycloaddition. -6 Thymidine derivatives of type (IV) are prepared and tested for their inhibitory effects against the replication of HIV-1 (IIIB) and HIV-2 (ROD). No marked activity is found. -(TOURIRTE, M.; OULIH, T.; LAZREK*, H. B.; BARASCUT, J. L.; IMBACH, J. L.; ALMASOUDI, N. A.; Nucleosides,

Synthesis and Antiviral Activities of 1,2,3-triazole Functionalized Thymidines: 1,3-dipolar Cycloaddition for Efficient Regioselective Diversity Generation

“…Certain 1,2,3-triazole nucleosides have been reported to possess potent anti-HIV-1 activities and have exhibited high activity against 10 selected HIV mutants (Alvarez et al, 1994;Brzozowski, 1998). Generation of the 1,2,3-triazole moiety in the 3′-position of 2′-deoxyribose nucleosides through the 1,3-dipolar cycloaddition of organic azides with alkynes has been reported (Häbich et al, 1989;Wigerinck et al, 1989;Tourirte et al, 2003). Since the 1,3-dipolar cycloaddition of organic azides with alkynes was introduced by Huisgen (1984) and developed further using a copper (I) catalyst (Rostovtsev et al, 2002;Tornøe et al, 2002), this chemoselective ligation reaction has been widely used and applied in drug discovery, materials synthesis and bioconjugate chemistry.…”