5-(substituted/unsubstituted benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazides 1a-b  on reaction with phenylisothiocyanate, potassium thiocyanate, carbon disulphide in pyridine and carbon disulphide in KOH followed by hydrazine hydrate afforded nitrogenous, sulphur bridgehead heterocycles 2-5a-d respectively. The structures of the newly synthesized compounds were elucidated by elemental analysis and spectral data such as IR, 1H NMR, 13C NMR and mass spectra. In addition the in vitro antibacterial and antifungal properties were tested for these synthesized compounds against B. subtilis, S. aureus, E. coli, P. aeruginosa and A. niger compared with ampicillin and clotrimazole as reference drugs. Synthesized compounds were found to possess moderate to excellent activity against selected strains.