Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6‑Substituted 7‑(Het)aryl-7-deazapurine Ribonucleosides

Abstract

A series of 80 7-(het)­aryl- and 7-ethynyl-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)­aryl-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against <i>Mycobacterium bovi</i>s and also against hepatitis C virus in a replicon assay