Synthesis and Anti-Biofilm Activity Studies on Novel Quinazolinone-Thiadiazole Hybrids
Year 2025,
Volume: 15 Issue: 1, 170 - 174, 28.03.2025
Sevda Türk
,
Seyhan Ulusoy
,
Sevgi Karakuş
,
Gülgün Tınaz
Abstract
Objective: In this study it was aimed to synthesize novel 1,3,4-thiadizole bearing 4(3H)-quinazolinone compounds, elucidate their structure and evaluate their anti-biofilm activity.
Methods: Four novel 4(3H)-quinazolinone compounds (1-4) were synthesized with a two step reaction starting from 5-bromoanthranilic acid. Their anti-biofilm activity was investigated.
Results: The final compounds’ structures were clarified by elemental analysis and spectroscopic methods (IR, 1H-NMR, 13C-NMR and MS). In the result of anti-biofilm activity studies, they possessed 26.0-30.0% biofilm formation inhibition.
Conclusion: Among the tested compounds, 6-bromo-3-{4-[5-(4-nitrophenylamino)-1,3,4-thiadiazol-2-yl]phenyl}-2-methylquinazolin-4(3H)-one formulated compound 3 was found as the most active one with 30.0% biofilm formation inhibition.
Ethical Statement
This study didn’t need an Ethics Committee Approval.
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Year 2025,
Volume: 15 Issue: 1, 170 - 174, 28.03.2025
Sevda Türk
,
Seyhan Ulusoy
,
Sevgi Karakuş
,
Gülgün Tınaz
References
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- Deng Y, Chen M, Yi J, Zheng Y. Design, synthesis, and anti–tobacco mosaic virus activity evaluation of quinazolinone derivatives containing purine moieties. Phytochem Lett. 2024; 59: 10-14. https://doi.org/10.1016/j.phytol.2023.11.003
- Qhobosheane MA, Legoabe LJ, Petzer A, Petzer JP. The monoamine oxidase inhibition properties of C6-mono- and N3/C6-disubstituted derivatives of 4(3H)-quinazolinone. Bioorg Chem. 2019; 85: 60-65. https://doi.org/10.1016/j.bioorg.2018.12.030
- Khalifa MM, Sakr HM, Ibrahim A, Mansour AM, Ayyad RR. Design and synthesis of new benzylidene-quinazolinone hybrids as potential anti-diabetic agents: In vitro α-glucosidase inhibition, and docking studies. J Mol Struct. 2022; 1250: 131768. https://doi.org/10.1016/j.molstruc.2021.131768
- Tokalı FS, Sağlamtaş R, Öztekin A, Yırtıcı Ü, Çomaklı V. New diacetic acids containing quinazolin-4(3H)-one: Synthesis, characterization, anticholinergic properties, DFT analysis and molecular docking studies. Chemistry Select 2023; 8(e202205039): 1-9. https://doi.org/10.1002/slct.202205039
- Moftah HK, Mousa MHA, Elrazaz EZ, Kamel AS, Lasheen DS, Georgey HH. Novel quinazolinone Derivatives: Design, synthesis and in vivo evaluation as potential agents targeting Alzheimer disease. Bioorg Chem. 2024; 143: 107-065. https://doi.org/10.1016/j.bioorg.2023.107065
- Bouley R, Ding, D, Peng Z, Bastian, M, Lastochkin E, Song W, Suckow MA, Schroeder VA, Wolter WR, Mobashery S, Chang M. Structure−activity relationship for the 4(3H)‑quinazolinone antibacterials. J Med Chem. 2016; 59: 5011-5021. https://doi.org/10.1021/acs.jmedchem.6b00372
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- Liu T, Peng F, Cao X, Liu F, Wang Q, Liu L, Xue W. Design, synthesis, antibacterial activity, antiviral Activity, and mechanism of myricetin derivatives containing a quinazolinone moiety. ACS Omega 2021; 6: 30826-30833. https://doi.org/10.1021/acsomega.1c05256
- Rasapalli S, Murphy ZF, Sammeta VR, Golen JA, Weig AW, Melander RJ, Melander C, Macha P, Vasudev MC. Synthesis and biofilm inhibition studies of 2-(2-amino-6-arylpyrimidin-4-yl)quinazolin-4(3H)-ones. Bioorg Med Chem Lett. 2020; 30: 127550. https://doi.org/10.1016/j.bmcl.2020.127550
- Rakesh KP, Kumara HK, Ullas BC, Shivakumara J, Gowda DC. Amino acids conjugated quinazolinone-Schiff’s bases as potential antimicrobial agents: Synthesis, SAR and molecular docking studies. Bioorg Chem. 2019; 90: 103093. https://doi.org/10.1016/j.bioorg.2019.103093
- Türk S, Karakuş S, Maryam A, Oruç-Emre EE. Synthesis, characterization, antituberculosis activity and computational studies on novel Schiff bases of 1,3,4-thiadiazole derivatives. J Res Pharm. 2020; 24(6): 793-800. https://doi.org/10.35333/jrp.2020.232
- Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur J Med Chem. 2007; 42: 235-242. https://doi.org/10.1016/j.ejmech.2006.10.003
- Türk S, Karakuş S, Ece A, Ulusoy S, Boşgelmez-Tınaz G. Synthesis, structure elucidation and biological activities of some novel 4(3H)-quinazolinones as anti-biofilm agents. Lett Drug Des Discov. 2019; 16: 313-321. https://doi.org/10.2174/1570180815666180621101123
- Türk S, Turan K, Ulusoy S, Karakuş S, Boşgelmez-Tınaz G. Synthesis, characterization and biological activity studies on amide derivatives. Istanbul J Pharm. 2018; 48(3): 76-81. https://doi.org/10.26650/IstanbulJPharm.2018.18007
- Karakus S, Kocyigit-Kaymakcioglu B, Toklu HZ, Aricioglu F, Rollas S. Synthesis and anticonvulsant activity of new N-(alkyl/substitutedaryl)-N'-4-(5-cyclohexylamino)-1,3,4-thiadiazole-2-yl)phenythioureas. Arch Pharm. 2009; 342(1): 48-53. https://doi.org/10.1002/ardp.200800118
- Ulusoy S, Akalın RB, Çevikbaş H, Berisha A, Oral A, Boşgelmez-Tinaz G. Zeolite 4A as a jammer of bacterial communication in Chromobacterium violaceum and Pseudomonas aeruginosa. Future Microbiol. 2022; 17(11), 861-871. https://doi.org/10.2217/fmb-2021-0174
- Uraz M, Karakuş S, Mohsen UA, Kaplancıklı ZA, Rollas S. The synthesis and evaluation of anti-acetylcholinesterase activity of some 4(3H)-quinazolinone derivatives bearing substituted 1,3,4-thiadiazole. Marmara Pharm J. 2017; 21: 96-101. https://doi.org/10.12991/marupj.259886