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A new series of 20 benzofuran based sulphonamides was synthesized from salicylaldehyde and ortho-vanillin. Synthesized compounds (VIIIa–VIIIt) were characterized using FT-IR (Fourier-transform infrared spectroscopy), 1H-NMR (Proton nuclear magnetic resonance) and Mass spectroscopic studies. All 20 compounds were subjected to in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strains. Compounds (VIIIj), (VIIIi), (VIIIo) and (VIIId) were found to exhibit lower MICs (the minimum inhibitory concentrations) as 13, 18, 17 and 19 µg/mL respectively. To predict plausible modes of binding of these compounds, we carried out molecular docking analysis against a target type III polyketide synthase PKS18 from M. tuberculosis (PDB ID: 1TED). [ABSTRACT FROM AUTHOR]