3-Amino-2-(substituted phenoxymethyl / propyl) quinazolin4(3H)ones 4a-c have been prepared. Refluxing 4 with 5-nitro-2furaldehyde / 4-nitrobenzaldehyde afforded the corresponding substituted methylidene-amino derivatives 5 and 6 respectively. Reaction of 4 with isatin yielded the indolylideneamino derivatives 7. Refluxing 4 with ofloxacin acid chloride furnished the corresponding carboxamides 8. Reaction of chloroacetyl chloride with 4c produced the 3-chloroacetylamino derivative 9 which upon further reaction with the potassium salts of some antibacterial acids gave the corresponding carboxylate derivatives 10. Sixteen compounds were screened for their antibacterial and antifungal activities. Thirteen compounds were found to possess (high to moderate) activity against Pseudomonas aerugenosa and some of them were also active against Escherichia coli. Only one compound was found to exhibit moderate antifungal activity against Candida albicans.