A series of 6-tosyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide analogues are synthesized by conventional techniques and characterized by elemental analysis, IR, MS, H-1, and C-13 NMR. These are tested for their antibacterial activity against Bacillus subtilis (abbreviated as BS), Staphylococcus aureus (abbreviated as SA), and Escherichia coli (abbreviated as EC). The synthesized compounds are able to inhibit the growth of the SA and EC. None of the compounds are effective against BS. All valence molecular orbital (abbreviated as MO) calculations with PM6 have been carried out for the molecules for which bioactivity data are available. Ciprofloxacin is taken as the standard antibiotics to compare activity with the molecules synthesized. It has been attempted to correlate the activity of the molecules with their electronic structure.