Synthesis and pharmacological evaluation of some 3-(4-methoxyphenyl)-2- substitutedamino-quinazolin-4(3H)-ones as analgesic and anti-inflammatory agents

Abstract

A variety of novel 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)- ones were synthesized by reacting the amino group of 2-hydrazino-3-(4- methoxyphenyl)-quinazolin-4(3H)-one with a variety of alkyl and aryl ketones. The starting material 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 4-methoxyaniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. While the test compounds exhibited significant activity, compounds 2-(1-methylpropylidene)- hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A1), 2-(1-ethylpropylidene)- hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A2) and 2-(1- methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent analgesic activity and the compound 2-(1- methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent anti-inflammatory activity when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to aspirin. © 2007 Pharmaceutical Society of Japan.