Abstract
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.
Highlights
The alarming rise of cancer cases has put strains on individuals, families and the society in which they live
As per a report by world health organisation (WHO), it is estimated the number of new cancer cases will rise by about 70% over the two decades [1]
In continuation of our research works on linomide, we proposed the synthesis of novel linomide analogues by modifying substitutions on ring nitrogen, isosteric replacement of oxygen by substituted nitrogen and preparing mannich bases by exploiting the acidic hydrogen of the acetyl group
Summary
The alarming rise of cancer cases has put strains on individuals, families and the society in which they live. As per a report by world health organisation (WHO), it is estimated the number of new cancer cases will rise by about 70% over the two decades [1]. The quinolin-2-one moiety exhibits a versatile range of biological activity. The natural compounds containing the quinolin-2-one nucleus such as flindersine, dictamnine as well as their synthetic analogues are found to possess pharmacological activity and therapeutic utility [2,3,4,5]. Clinical significance of quinolin-2-one is well established and documented in the form of treatment of psychosis, as a β-blocker in an ophthalmic preparation, as an antacid and in congestive cardiac failure [6,7,8,9]
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