Objective: The aim of this study was to the synthesis of indole, coumarinyl and pyridinyl derivatives of isoniazid as potent anti-TB and antimicrobial agents and their molecular docking studies. Methods: The structures of the newly synthesized compounds were confirmed by FT-IR, ¹HNMR, and Mass spectroscopic methods and to evaluate the biological studies like anti-TB, antimicrobial and antioxidant activities. The mode of action of these active compounds was carried out by molecular docking studies. Results: Among all the synthesized compounds tested 5d was found to be the most active with M. tuberculosis H₃₇Rv strain at 12.5µg/ml, 5b at 25µg/ml, 4d was found to be the most active with S. typhi, S. aureus and A. Nizer, 5a with A. Oryzae, 5c with A. terrous and A. Flavous and 5d with Shegella at 100µg/ml and some of the compounds like 4d, 5a, 5b and 5d have shown promising antioxidant properties. Conclusion: All the synthesized compounds have exhibited promising anti-TB, antimicrobial and antioxidant activities.