Thienopyridines one of the most important classes in organic chemistry due to their outstanding medicinal and environmental applications. In this study, we report the synthesis of a series of novel thienopyridine derivatives bearing different aryl substituents on the fused thiophene moiety to showcase their inhibition behavior on different strains of bacteria and Fungai which can further be evidenced by molecular docking. The 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile (3) was used as a starting material for the synthesis of the target compounds (4-15). The condensation of compound 3 with thiophene-2-carbaldehyde led to formation of thienylpyridine product 4, which subsequently reacted with ethyl chloroacetate or chloroacetaldehyde to furnish the thienopyridine derivatives (6,7). Moreover, the alkylation of compound 3 with various bromoalkyl ketones followed by Thorpe-Zeigler cyclization furnished the …