Open AccessSYNTHESIS, CHARACTERIZATION AND EVALUATION OF 4-HYDROXY-1-PHENYL/METHYL-3-(3-SUBSTITUTED-1-(SUBSTITUTEDIMINO) PROPYL) QUINOLINE-2(1H)-ONE DERIVATIVES AND 4-HYDROXY-1-PHENYL/METHYL-3-(1-(SUBSTITUEDIMINO) ETHYL) QUINOLINE-2(1H)-ONE DERIVATIVES AS POSSIBLE ANTICANCER AGENTS
Author(s) -
Shyam Desai,
Rudrax N. S. Priolkar,
Harshank A. Naik Karmali,
Prabhav D. Ambe,
B. S. Biradar
Publication year - 2017
Publication title -
international journal of pharmacy and pharmaceutical sciences/international journal of pharmacy and pharmaceutical sciences
Language(s) - English
Resource type - Journals
eISSN - 2656-0097
pISSN - 0975-1491
DOI - 10.22159/ijpps.2017v9i10.20184
Subject(s) - chemistry , quinoline , bromide , mtt assay , stereochemistry , in vitro , ic50 , medicinal chemistry , organic chemistry , biochemistry
Objective: Synthesis, characterization and evaluation of quinolin-2-one derivatives as possible anticancer agents.Methods: A series of novel 4-hydroxy-1-phenyl/methyl-3-(3-substituted-1-(substitutedimino)propyl)quinolin-2(1H)-one derivatives IIa(1-5)/IIb(1-5) and 4-hydroxy-1-phenyl/methyl-3-(1-(substituedimino)ethyl)quinolin-2(1H)-one derivatives IIIa(1-3)/IIIb(1-3) were synthesised by nucleophilic addition of substituted anilines on 3-acetyl-4-hydroxy-1-phenyl/methylquinolin-2(1H)-one (a/b) and 4-hydroxy-3-(3-substitutedpropanoyl)-1-phenyl/methyl quinolin-2(1H)-one (Ia/Ib); respectively. The synthesised derivatives were characterised by spectral analysis and were tested for their in vitro anticancer activity against K562 and Hep 3b cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay method.Results: The compounds were tested for their in vitro anticancer activity against K562 and Hep 3b cell lines at 10, 20, 25, 30 and 50 µg/ml concentration using MTT assay method. The compound 4-hydroxy-3-(3-morpholino-1-(phenylimino)propyl)-1-phenylquinolin-2(1H)-one (IIa-1) showed anticancer activity with IC50 value 20 µg as compared to the control against K562 cell lines. The compound 4-hydroxy-1-phenyl-3-(1-(phenylimino) ethyl) quinolin-2(1H)-one (IIIa-1) showed anticancer activity with IC50 value less than 10 µg.Conclusion: The proposed method for the synthesis of novel derivatives is convenient and gives a good yield. Some of the synthesised compounds showed promising anticancer activity against K562 and Hep 3b cell lines. Compound IIa-1 (R=-C6H5; R1= morpholine; R2= C6H5-NH-) exhibited most potent activity against K562 cell lines. Compound IIIa-1 (R=-C6H5; R3= C6H5-NH-) has been proved to be the most cytotoxic compound among the other derivatives against Hep 3b cell lines.