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Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7‑Deazapurine Ribonucleosides
Two
isomeric series of new thieno-fused 7-deazapurine ribonucleosides
(derived from 4-substituted thieno[2′,3′:4,5]pyrrolo[2,3-<i>d</i>]pyrimidines and thieno[3′,2′:4,5]pyrrolo[2,3-<i>d</i>]pyrimidines) were synthesized by a sequence involving
Negishi coupling of 4,6-dichloropyrimidine with iodothiophenes, nucleophilic
azidation, and cyclization of tetrazolopyrimidines, followed by glycosylation
and cross-couplings or nucleophilic substitutions at position 4. Most
nucleosides (from both isomeric series) exerted low micromolar or
submicromolar in vitro cytostatic activities against a broad panel
of cancer and leukemia cell lines and some antiviral activity against
HCV. The most active were the 6-methoxy, 6-methylsulfanyl, and 6-methyl
derivatives, which were highly active to cancer cells and less toxic
or nontoxic to fibroblasts