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Published on:August 2020
Indian Journal of Pharmaceutical Education and Research, 2020; 54(3):771-780
Original Article | doi:10.5530/ijper.54.3.129

Novel Quinolone Substituted Imidazol-5(4H)-ones as Anti-inflammatory, Anticancer Agents: Synthesis, Biological Screening and Molecular Docking Studies

Authors and affiliation (s):

Santosh Kumar1, Jignesh C Aghara1, Anirudh Manoj1, Angel T Alex2, Jesil Mathew A2, Alex Joesph1,*

1Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal, Karnataka, INDIA.

2Department of Pharmaceutical Biotechnology, Manipal College of Pharmaceutical Sciences, Manipal, Karnataka, INDIA.


Background: Quinolones and, imidazolones are important heterocyclic moieties which have been reported to possess potent anti-inflammatory and anticancer properties. The activity of these compounds were related to inhibition of nuclear factor-kappaB (NF- κB) which is one of the important targets studied for designing of anti-inflammatory and antitumor drugs. Further, hybrid pharmacophore approach is used in the present study for designing potent molecules. Objectives: Aim of the study is to synthesis a series of quinolone substituted imidazolones and evaluation of their anti-inflammatory and anticancer activity. Methods: Quinolone substituted imidazolones were synthesized by aminolysis of 7-amino-4-methyl-quinoline-2(1H)-one with substituted oxazolones afforded quinolone substituted imidazolones. Structures of synthesized compounds were characterized by spectral techniques and were evaluated for anti-inflammatory activity by carrageenan-induced rat paw oedema test. Differences between control and treatment groups were tested using one way analysis of variance followed by Tukey’s test. Anticancer activity was assessed by evaluating the cytotoxicity of compounds on BT-549 and HeLa, human cancer cell lines by MTT assay. Results: Compounds 3-fluorobenzylidene substituted imidazolonyl quinolone (F3) and 4-phenoxybenzylidene substituted imidazolonyl quinolone (F12) were the most cytotoxic compounds against BT-549 and HeLa cell lines. While 2-chlorobenzylidene substituted imidazolonyl quinolone (F4) and 4-chlorobenzylidene substituted imidazolonyl quinolone (F5) exhibited the highest anti-inflammatory activity. Most of the test compounds exhibited statistically significant inhibition of paw oedema volume when compared to that of control. Conclusion: Molecular docking studies revealed that combination of two pharmacophores was crucial for binding of quinolone substituted imidazol-5(4H)-ones on NF-κB with good correlation between docking score and biological activity.

Key words: Anti-inflammatory, Anticancer, Docking, Quinolone, Imidazolone, NF-κB.



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The Official Journal of Association of Pharmaceutical Teachers of India (APTI)
(Registered under Registration of Societies Act XXI of 1860 No. 122 of 1966-1967, Lucknow)

Indian Journal of Pharmaceutical Education and Research (IJPER) [ISSN-0019-5464] is the official journal of Association of Pharmaceutical Teachers of India (APTI) and is being published since 1967.


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