Alkylation of 4,6-diamino-3-cyanopyridine-2(1H)-thione (1) with active halo compounds namely; ethyl chloroacetate, chloroacetic acid, 2-chloro-N-phenylacetamide, chloroacetonitrile, or chloroacetamide gave S-alkyl derivatives 2-6, respectively. Thienopyridine derivatives 7-10 were furnished by heating of S-alkyl derivatives 2-6 in hot KOH solution or by reaction of compound 1 with appropriate halo compound directly in hot KOH solution. The reaction of compound 1 with 3-bromopentane-2,4-dione or ethyl 2-bromo-3-oxobutanoate afforded 2-acetylthienopyridine 11. Cyanoethylthiopyridine 12 yielded via the addition of acrylonitrile with compound 1. The potency of the results as antibacterial and antifungal agents has been evaluated. The compounds have been characterized based on their IR, 1H NMR, 13C NMR and elemental analysis.