DESIGN, SYNTHESIS AND PSYCHOPHARMACOLOGICAL ACTIVITY OF QUINOLIN-2-ONE DERIVATIVES

Starting material 4-hydroxy-1-phenyl/methyl-quinolin-2-(1H)-one was treated with phosphorous oxychloride and then subjected to Mannich reaction to yield title 4-chloro-1-phenyl/methyl-3-[3- (substituted) propanoyl] quinolin-2(1H)-one derivatives compounds IIa (1-7)/ IIb (1-7). Molecular docking studies of the compounds were carried out using Molegro Virtual Docker. All the synthesized compounds were characterized by IR, 1H-NMR and Mass Spectral data and were tested for their antidepressant activity. Amongst the synthesized compounds, compound 4-chloro-1-phenyl-3-[3-(morpholinopropanoyl] quinolin-2(1H)-one [IIa4] was found to show the most potent antidepressant activity with immobility time of 98.17± 4.806. Compound 4-chloro-1-phenyl-3-[3-(4- methylpiperazin-1-yl) propanoyl] quinolin-2(1H)- one [IIa 3] and 4-chloro-1-methyl-3-[3-(pyrrolidin-1-yl) propanoyl] quinolin-2(1H)-one [IIb 2] showed moderate antidepressant activity with immobility time of 126.5 ± 1.945s and 120.3 ± 2.376s, respectively, compared to standard imipramine.