The SYNTHESIS, SCREENING OF NOVEL 1-SUBSTITUTED-3-(4-OXO-2-PHENYLQUINAZOLIN-3(4H)-yl) UREA AND THIOUREA ANALOGUES AS POTENT ANTIBACTERIALS
The proposed study is an attempt to determine antibacterial activity of synthesized novel 1-substituted-3-(4-oxo-2-phenylquinazolin-3(4H)-yl) urea and thiourea analogues as potent antibacterials against against S. aureus and E. coli bacteria.
Reagents used in the present study were of synthetic grade and solvents were used after distillation. Novel quinazolinone analogues were synthesized by considering substitution pattern, characterization of the synthesized analogues was performed using various techniques like Thin layer chromatography, Melting point, Infrared spectroscopy, Proton NMR spectrometry and Mass spectrometry.
Six derivatives of quinazolinone analogues were synthesized. The structures of 1-substituted-3-(4-oxo-2-phenylquinazolin-3(4H)-yl) urea and thiourea derivatives were confirmed by physical and spectral analysis. The compounds were assayed for antibacterial activity against S. aureus and E. coli using ciprofloxacin as standard. The synthesized analogues have shown good yield and comparable antibacterial activity.
The present study delivers a convenient and efficient protocol for the quinazolinone analogues synthesis.
1. Samira I, Patel S, Hasmin M, Patel S. Biological profile of quinazoline. Int J Pharm Chem Sci: 2012; 1:1863-1872.
2. Jafari E, Khajouei MR, Hassanzadeh F, Hakimelahi GH, Khodarahmi GA. Quinazolinone and quinazoline analogues: recent structures with potent antimicrobial and cytotoxic activities. Res Pharm Sci: 2016; 1:1-14.
3. Schroeder LA, Gries TJ, Saecker RM, Record Jr MT, Harris ME, deHaseth PL. Evidence for a tyrosine–adenine stacking interaction and for a short-lived open intermediate subsequent to initial binding of Escherichia coli RNA polymerase to promoter DNA.
J Mol Biol. 2009; 16:339-349.
4. Zhang K, Lai F, Lin S, et al. Design, synthesis and biological evaluation of 4-methyl quinazoline derivatives as anticancer agents simultaneously targeting phosphoinositide 3-kinases and histone deacetylases. J Med Chem. 2019; 62: 6992-7014.
5. Muthu K, Madhavi M, Kiana N, Aparna S, Kishor S. Topoisomerase as a target for antibacterial and anticancer drug discovery. J. Enzyme Inhib Med Chem; 2013; 28: 419-435.
6. Mohamed M, Ghanem H, Abd F, Mohamed S. Biological evaluation and molecular docking of substituted quinazolinones as antimicrobial agents. Aust J Basic Appl Sci. 2013; 7: 263–274.
7. Suresha P, Prakasha C, Kumara S, Kapfo W, Gowda C. Design and synthesis of heterocyclic conjugated peptides as novel antimicrobial agents. Int J Pept Res The. 2009; 15:25-30.
8. Rana M, Desai R, Jauhari S. Synthesis, characterization, and pharmacological evaluation of 1-[2-(6-nitro-4-oxo-2-phenyl-4H-quinazolin-3-yl)-ethyl]-3-phenyl ureas. Med Chem Res. 2013; 22: 225-233.
9. Olomola O, Akinpelu A, Obafemi A. Microwave-assisted synthesis and antibacterial activity of some quinazolinone analogues. J. Pharm. Res. 2013; 6: 6337.
10. Zeinyeh W, Esvan J, Josselin B, et al. Kinase inhibitions in pyrido[4,3-h] and [3,4-g]quinazolines: Synthesis, SAR and molecular modeling studies. Bioorg Med Chem. 2019; 27: 2083-2089.
11. Dahiya R, Kumar A, Yadav R. Synthesis and biological activity of peptide analogues of iodoquinazolinones/nitroimidazoles. Molecules. 2008; 13: 958-976.
12. Rajveer CH, Kumaraswamy S. Rathinaraj. SB: Synthesis of some 6-bromo quinazolinone analogues for their pharmacological activities. Int J Pharma Bio Sci: 2010; 2: 50-56.
13. Messali M, Aouad MR, et al. Synthesis, characterisation and POM analysis of novel bioactive imidazolium-based ionic liquids. Med Chem Res.2015; 24: 1387-1395.
14. Gemma S, Camodeca C, Brindisi M, et al. Mimicking the intramolecular hydrogen bond: synthesis, biological evaluation, and molecular modeling of benzoxazines and quinazolines as potential antimalarial agents. J Med Chem. 2012; 55: 10387-10404.
15. Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J Pharm Anal. 2016; 6: 71-79.
16. Pavia D, Lampmanh H, Kvizgeorge. Introduction to Spectroscopy. 3rd ed.: Cengage Learning: 2017.
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