The present paper proposed the tri-potassium phosphate catalyzed synthesis of some novel series of Schiff bases (3a to 3l) derived from 2-aminopyridine using microwave technique. All synthesized Schiff bases were confirmed by different spectroscopic methods. Further all synthesized imines have been evaluated to screen for antimicrobial, antioxidant and anti-inflammatory activity. The compound 3c displays potent anti-inflammatory activity with 42.307%±1.322 inhibition of inflammation. The antioxidant activity data revealed that all synthesized Schiff bases exhibit potency to scavenge DPPH and nitric oxide radicals. Antimicrobial properties of these compounds showed moderate to excellent growth of inhibitory activity against various tested pathogens. Our observations and examination for pharmacological study towards the presence of active pharmacological functional groups present in the main structural nucleus of synthesized imines. Therefore, present study may lead to the development of a new class of anti-inflammatory and antioxidant drugs with structural modification.