• SANDHYA R. DHOKALE Department of Pharmaceutical Chemistry, Poona College of Pharmacy, Bharati Vidyapeeth (Deemed to be University), Pune 411038, Maharashtra, India
  • SNEHAL R. THAKAR Department of Pharmaceutical Chemistry, Poona College of Pharmacy, Bharati Vidyapeeth (Deemed to be University), Pune 411038, Maharashtra, India
  • DEEPALI A. BANSODE Department of Pharmaceutical Chemistry, Poona College of Pharmacy, Bharati Vidyapeeth (Deemed to be University), Pune 411038, Maharashtra, India
  • KAKASAHEB R. MAHADIK Principal, Poona College of Pharmacy, Bharati Vidyapeeth (Deemed to be University), Pune 411038, Maharashtra, India


Objective: 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 S. aureus and E. coli bacteria.

Methods: The present study reports new series of 1-substituted-3-(4-oxo-2-phenylquinazolin-3(4H)-yl) urea and thiourea derivatives as potent antibacterial agents. 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. TLC of the synthesized analogues was carried out by using (toluene: methanol in the ratio 2:1), melting point was found by open capillary method, IR spectrum was recorded on JASCO V-530, 1H NMR was recorded on Bruker Avance Spectrometer and Mass spectra were obtained from G6460A, triple quadrupole/MS/MS system. In vitro antibacterial activity was performed against S. aureus and E. coli.

Results: 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. Synthesized molecules showed Rf of 0.45-0.80 in toluene: methanol mobile phase, melting point was carried out by open capillary method and were in range of 90-210 ° C, IR spectrum was recorded in range of 14000-400 cm-1and showed characteristic peaks of NH and of C-O-NH, 1H NMR of the compounds was distinct to confirm structures with delta values in the range of 7.53-11.960, Mass spectra proved parent peaks of synthesized compounds confirming molecular weight. 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.

Conclusion: The present study delivers a convenient and efficient protocol for the quinazolinone analogues synthesis.

Keywords: Antibacterial, Ciprofloxacin, E. coli, Quinazolinone analogues, S. aureus


Download data is not yet available.


1. Samira I, Patel S, Hasmin M, Patel S. Biological profile of quinazoline. Int J Pharm Chem Sci 2012;1:1863-72.
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, de Haseth 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;16:339-49.
4. Zhang K, Lai F, Lin S. 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;28:419-35.
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;7:263–74.
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;22:225-33.
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. Kinase inhibitions in pyrido[4,3-h] and [3,4-g]quinazolines: Synthesis, SAR and molecular modeling studies. Bioorg Med Chem 2019;27:2083-9.
11. Yadav MK, Tripathi L, Goswami D. Synthesis and anticonvulsant activity (Chemo shock) of N-1(substituted-n-4[(4-oxo-3-phenyl-3, 4-dihydro-quinazoline-2-ylmethyl) semicarbazones. Asian J Pharm Clin Res 2017;10:359–66.
12. Mungra DC, Patel MP, Rajani DP, Patel RG. Synthesis and identification of ?-aryloxyquinolines and their pyrano[3,2-c] chromene derivatives as a new class of antimicrobial and antituberculosis agents. Eur J Med Chem 2011;46:4192-200.
13. Kapoor B, Nabi A, Gupta R, Gupta M. Synthesis and antimicrobial evaluation of quinazolinone peptide derivatives. Asian J Pharm Clin Res 2017;10:7–12.
14. Priya D, Srimathi R, Anjana GV. Synthesis and evaluation of some mannich bases of quinazolinone nucleus. Asian J Pharm Clin Res 2018;11:407–9.
15. Niraj Kumar Sinha, Alpana J Asnani. Novel approach towards development of quinazoline derivatives in pain management. Asian J Pharm Clin Res 2013;6:200-4.
16. Megha Sahu, Amit G Nerkar. In silico screening, synthesis and in vitro evaluation of some quinazolinone derivatives as dihydrofolate reductase inhibitors for anticancer activity: Part-I. Int J Pharm Pharm Sci 2014;6:193-9.
17. Dahiya R, Kumar A, Yadav R. Synthesis and biological activity of peptide analogues of iodoquinazolinones/nitroimidazoles. Molecules 2008;13:958-76.
18. Rajveer CH, Kumaraswamy S, Rathinaraj SB. Synthesis of some 6-bromo quinazolinone analogues for their pharmacological activities. Int J Pharma Bio Sci 2010;2:50-6.
19. Messali M, Aouad MR. Synthesis, characterisation and POM analysis of novel bioactive imidazolium-based ionic liquids. Med Chem Res 2015;24:1387-95.
20. Gemma S, Camodeca C, Brindisi M. Mimicking the intramolecular hydrogen bond: synthesis, biological evaluation, and molecular modeling of benzoxazines and quinazolines as potential antimalarial agents. J Med Chem 2012;55:10387-404.
21. Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: a review. J Pharm Anal 2016;6:71-9.
22. Pavia D, Lampmanh H, Kvizgeorge. Introduction to Spectroscopy. 3rd ed.: Cengage Learning; 2017.
23. Zhijiang Fan. Synthesis, crystal structure and agricultural antimicrobial evaluation of novel quinazoline thioether derivatives incorporating the 1,2,4-triazolo[4,3-a]pyridine moiety. J Agric. Food Chem 2019;67:1-37.
24. Buggana S, Paturi M, Perka H, Gade D, VVS R. Novel 2,4-disubstituted quinazolines as cytotoxic agents and JAK2 inhibitors: synthesis, in vitro evaluation and molecular dynamics studies, comput. Biol Chem 2019;153:39-47.
25. Karuna S, Naresh P, Katari K, Jonnalagadda S. Design and synthesis of novel 6-substituted quinazoline-2-thiols. Mol Divers 2019;23:351–60.
26. Jacob B, Bisht L, Chandy V. 3D QSAR studies of 2, 3-disubstituted quinazoline phenyl acetic acid derivatives as antimicrobial agents. Res Rev: J Pharm Sci 2018;79:110-8.
27. Chen J, Sang Z, Jiang Y, Yang C, He L. Design, synthesis and biological evaluation of quinazoline derivatives as dual HDAC1 and HDAC6 inhibitors for the treatment of cancer. Chem Biol Drug Des 2019;93:232–41.
28. Faghihi K, Safakish M, Zebardast T, Hajimahdi Z, Zarghi A. Molecular docking and QSAR study of 2-benzoxazolinone, quinazoline and diazocoumarin derivatives as anti-HIV-1 agents. Ira J Pharm Res 2019;18:1253–63.
308 Views | 270 Downloads
How to Cite
DHOKALE, S. R., S. R. THAKAR, D. A. BANSODE, and K. R. MAHADIK. “The SYNTHESIS, SCREENING OF NOVEL 1-SUBSTITUTED-3-(4-OXO-2-PHENYLQUINAZOLIN-3(4H)-YL) UREA AND THIOUREA ANALOGUES AS POTENT ANTIBACTERIALS”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 11, no. 11, Nov. 2019, pp. 38-42, doi:10.22159/ijpps.2019v11i11.35461.
Original Article(s)