Synthesis and biological properties of 4-substituted quinolin-2(1H)-one analogues

Abstract

A variety of 4-substituted quinolin-2(1H)-ones were prepared and evaluated for N-methyl-D-aspartate (NMDA) receptor binding site activity and their abilities to inhibit neurotoxicity. The 4-(2-carbethoxyethanamino)- 7-chloro-3-nitroquinolin-2(1H)-one (9b) exhibited favorable NMDA receptor binding site activity and 7-chloro-4-(benzylamino)-3- nitroquinolin-2(1H)-one (9c) showed the most potent neurotoxicity among them. The synthetic strategies involve the use of well known keto ester condensation and reductive ring cyclization of intermediates (2a-d) to afford 4-substituted quinolin-2(1H)-ones.