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Thienopyrrolo[2, 3-d]pyrimidines, New Tricyclic Nucleobase Analogues: Synthesis and Biological Activities

Publication at Faculty of Science |


Three isomeric series of 4-substituted thieno-fused 7-deazapurine nucleobases were synthesized by palladium catalyzed couplings or nucleophilic substitutions from protected key-intermediate 4-chlorothienopyrrolopyrimidines. Most final nucleobases exerted micromolar activity against hepatitis C virus and respiratory syncytial virus, as well as some in vitro cytostatic activities against several cancer and leukemia cell lines.

Three new nucleosides derived from 8H-thieno[3',4':4,5]pyrrolo[2,3-d] pyrimidine were also synthesized and were significantly more cytostatic than corresponding nucleobases, with activities in submicromolar range and low toxicity to normal cycling fibroblasts.