Novel quinolone substituted quinazolin-4(3h)-ones as anti-inflammatory, anticancer agents: Synthesis and biological screening

Santosh Kumar, Jignesh Chhaganbhai Aghara, Angel Treasa Alex, Jesil Mathew Aranjani, Alex Joesph

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


Background: Quinolones and, quinazolinones are important pharmacodynamic heterocyclic nuclei which when incorporated into different heterocyclic templates, have been reported to possess potent anti-inflammatory and anticancer properties. The activity of these compounds were associated with inhibition of nuclear factor-kappaB (NF-κB) which is one of the important targets studied for designing of anti-inflammatory and antitumor drug. Further, the combination of two pharmacophores on the same molecule is a well-established approach for designing of potent molecules and may further enhance their activity. Objectives: Aim of the study is to synthesis a series of quinolone substituted quinazolinones and evaluation of their anti-inflammatory and anticancer activity. Methods: Quinolone substituted quinazolin-4(3H)-ones were synthesized in two steps, first step involves synthesis of 7-amino-4-methyl-quinolin-2(1H)-one. Second step involves aminolysis of 7-amino-4-methyl-quinoline-2(1H)-one with substituted benzoxazines afforded quinolone substituted quinazolinones. Structures of synthesized compounds were characterized by spectral techniques. The synthesized compounds were evaluated for anti-inflammatory activity by carrageenan-induced rat paw oedema test and anticancer activity was assessed by evaluating the cytotoxic effect of synthesized compounds on BT-549 and HeLa, human cancer cell lines by MTT assay. Results: The synthesized compounds; 6, 7-dimethoxy-2-methyl-3-(4-methyl-2-oxo-1, 2-dihydroquinolin-7-yl)quinazolin-4(3H)-one (6d) was the most cytotoxic compound against HeLa and BT-549 human cancer cell lines. While the compounds 6,8-dibromo-2-methyl-3-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)quinazolin-4(3H)-one (6f) and 2-methyl-3-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)-7-nitroquinazolin-4(3H)-one (6g) exhibited the highest anti-inflammatory activity in carrageenan-induced paw oedema model. Conclusion: Molecular docking studies revealed that combination of two pharmacophores was crucial for binding of quinolone substituted quinazolin-4(3H)-ones on NF-κB and good correlation was observed between docking scores and biological activity of synthesized compounds.

Original languageEnglish
Pages (from-to)S268-S276
JournalIndian Journal of Pharmaceutical Education and Research
Issue number4
Publication statusPublished - 12-2018

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)


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