In the present investigation, two series of novel urea/thiourea-based quinazoline analogs (7a–g/8a–g) have been synthesized by introducing C–C Suzuki coupling between quinazoline and phenyl ring followed by condensation of various N-phenyl isocyanates/isothiocyanates. The synthesized analogs were investigated for their antimicrobial activity against two Gram-positive bacteria, three Gram-negative bacteria, and two fungal species. They were also tested for the antimycobacterial activity against Mycobacterium tuberculosis H37Rv. The biological screening data revealed that majority of the compounds have demonstrated noticeable activity (MIC; 6.25–50 lg/mL) against most of the microorganisms. All the synthesized analogs were well characterized through IR, 1 H NMR, 13C NMR, and elemental analyses.