Antimicrobial Activities of 3-Aryl-4-(benzenesulfonyloxy)-benzylideneamino-4,5-dihyro-1H-1,2,4-triazol-5-one Compounds

Year 2024, Volume: 11 Issue: 2, 117 - 129, 31.12.2024

Şule Gülden Talay , Evren Koç , Neslihan Mutlu , Gül Özdemir , Murat Beytur , Haydar Yüksek

https://doi.org/10.48138/cjo.1560092

Abstract

Çalışmanın sentez bölümünde, ilk olarak 3 adet 3-aril-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiğinin bir benzaldehid türevi olan 3-etoksi-4-hidroksibenzaldehidin trietilamin varlığında benzensulfonil klorür ile muamelesinden sentezlenen 3-etoksi-4-(benzensulfoniloksi)-benzaldehid ile ayrı ayrı muamelesinden karşın olan 3 adet 3-aril-4-(benzensulfoniloksi)-benzilidenamino-4,5-dihiro-1H-1,2,4-triazol-5-on bileşiği elde edilmiştir. 3 Adet 1,2,4-triazol türevli Schiff bazı bileşikleri olan 3-aril-4-[3-etoksi-4-(benzensulfoniloksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on’ların Klebsiella pneumoniae, Pseudomonas aeruginosa, Echerichia coli, Staphylococcus aureus, Entercoccus faecalis bakterileri üzerindeki antimikrobiyal etkileri disk difüzyon yöntemi ile araştırılmıştır. Yapılan araştırma sonucunda 3-p-klorobenzil-4-[3-etoksi-4-(benzensulfoniloksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on’un E. coli ve K. pneumoniae üzerinde antimikrobiyal etki gösterdiği, 3-m-klorobenzil-4-[3-etoksi-4-(benzensulfoniloksi) benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on’un da yalnızca K. pneumoniae üzerinde etkili olduğu belirlenmiştir.

Keywords

Schiff bazı, Antimikrobiyal aktivite, Disk difüzyon yöntemi

References

• Akan, M., (2006). “Staphylococcal Infections. Veterinary Microbiology (Bacterial Diseases), Aydın, N., Paracıkoğlu, J., (eds.). İlke Emek Yayınları, Ankara, 5-13.
• Arda, M., (2006). “Basic Microbiology 3rd Edition”. Medisan Yayınevi, Ankara, 56-58.
• Aydınlı Esen, A. (2006). “Antimicrobial Activities of Some Schiff Bases”, Master's Thesis, Ankara University, Graduate School of Natural and Applied Sciences, Ankara.
• Bagihalli, G.,B., Avaji, P. G., Patil, S.A., Prema, S. (2008). “Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases”, Badami European Journal of Medicinal Chemistry, 43, 2639-2649.
• Bahçeci, Ş., Yıldırım, N., Alkan, M., Gürsoy Kol, Ö., Manap, S., Beytur, M., & Yüksek. (2017). Investigation of antioxidant, biological and acidic properties of new 3-alkyl (aryl)-4-(3-acetoxy-4-methoxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones. The Pharmaceutical and Chemical Journal, 4 (4), 91-101.
• Bayrak, H., Demirbas, A., Alpay Karaoglu, Ş., Demirbas, N. (2009). “Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities”, European Journal of Medicinal Chemistry, 44, 1057-1066.
• Beytur, M. (2020). Fabrication of platinum nanoparticle/boron nitride quantum dots/6-methyl-2-(3-hydroxy-4- methoxybenzylidenamino)-benzothiazole (ıls) nanocomposite for electrocatalytic oxidation of methanol. Journal of the Chilean Chemical Society, 65, 4929-4933.
• Beytur, M., & Avinca, I. (2021). Molecular, electronic, nonlinear optical and spectroscopic analysis of heterocyclic 3-substituted-4-(3-methyl-2-thienylmethyleneamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5- ones: experiment and dft calculations. Heterocyclic Communications, 27(1), 1-16.
• Beytur, M., Manap, S., Özdemir, G., Gürsoy Kol, Ö., Aytemiz, F., Alkan, M., & Yüksek. (2019). Preparation of some new bis-[4-(3-alkyl/aryl-4, 5-dihydro-1H-1, 2, 4-triazol-5-on-4-yl)-azomethinphenyl] phtalate derivatives with their antioxidant and antimicrobial activities. Research Journal of Pharmaceutical Biological and Chemical Sciences, 10 (1), 426-436.
• Blagus, A., Cincic, D., Friscic, T., Kaitner, B., Stilinovic, V. (2010). “Aldehydes: Molecular And Crystal Structure, Tautomerısm, Quınoıd Effect, Coordınatıon Compounds”, Macedonian Journal of Chemistry and Chemical Engineering, 29 (2), 117-138.
• Chohan, Z.H., Sumrra, S.H., Youssoufi, M.H., Hadda, T.B. (2010). “Metal based biologically active compounds: Design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium(IV) complexes”, European Journal of Medicinal Chemistry, 45 (7), 2739-2747.
• Çiftçi, E., Beytur, M. Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V. A., Manap, S., & Yüksek. (2017). Synthesis, characterization, antioxidant and antimicrobial activities and DNA damage of some novel 2- [3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in human lymphocytes. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9 (5), 1760-1771.
• Cui, P.L., Li, X.L., Zhu, M.Y., Wang, B.H., Liu, J., Chen, H. (2017). “Design, synthesis and antimicrobial activities of thiouracil derivatives containing triazolo-thiadiazole as SecA inhibitors”, Eur. J. Med. Chem., 127, 159-165.
• Değirmencioğlu, S.M. (2010). “Synthesis of some Schiff bases metal komplexes and investigation of biological activities”, Master's Thesis, Selçuk University, Graduate School of Natural and Applied Sciences, Konya.
• Esendal, Ö.M. (2006). “Pseudomonas Infections. Veterinary Microbiology (Bacterial Diseases), Aydın, N., Paracıkoğlu, J., (eds.)”, İlke Emek Yayınları, Ankara, 15-29.
• Ghasemzadeh, M.A., Abdollahi-Basir, M.H., Elyasi, Z. (2018). “Synthesis of some novel imidazoles catalyzed by Co3O4 nanoparticles and evaluation of their antibacterial activities”, Comb. Chem. High Throughout Screen., 21, 1-10.
• Gürsoy Kol, Ö., Manap, S., Ozdemir, G., Beytur, M., Agdaş, E., Azap, F., Yuca, S., Alkan, M., & Yüksek, H. (2020). Synthesis, antioxidant and antimicrobial activities of novel 4-(2-cinnamoyloxy benzylidenamino )-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Heterocyclic Letters, 10(4), 575- 587.
• İzgür, M. (2006). “Enterobacterial infections. Veterinary Microbiology (Bacterial Diseases), Aydın, N., Paracıkoğlu, J., (eds.)”, İlke Emek Yayınları, Ankara, 109-127.
• Karaca, E.Ö. (2018). “Synthesis of New Schiff Some Compounds and Elucidation of Their Structures”, Politeknik Dergisi, 21 (1), 245-249.
• Kardaş, F., Manap, S., Gürsoy-Kol, Ö., Beytur, M.,& Yüksek, H.(2016).Synthesis and antioxidant properties of some 3-alkyl(aryl)-4-[3-ethoxy-2-(4-toluenesulfonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4- triazol-5-ones. Der Pharma Chemica, 8(18): 274-281.
• Kayapa, F., (2018). “Chitosan schiff base derivatives and their complexes: Synthesis, characterization, investigation of antimicrobial properties”, Master's Thesis, Nevşehir Hacı Bektaş Veli University, Institute of Science and Technology, Nevşehir.
• Koç, E., Yüksek, H., Beytur, M., Akyıldırım, O., Akçay, M., & Beytur, C. (2020). In vivo determination of antioxidant property of heterocyclic 4,5 dihydro-1H-1, 2, 4- triazol 5-one derivate in male rats (wistar albino). Bitlis Eren University Journal of Science, 9, 542-548.
• Murray, P.R., Rosenthal, K.S., Pfaller, M.A. (2016). “Medical Microbiology. Enterocoocus and Other Gram-Positive Cocci, Us, A.D., Başustaoğlu, A., (ç.Ed.)”, Elsevier Limited, 205-208.
• Nastasa, C., Vodnar, D.C., Ionut, I., Stana, A., Benzdec, D., Tamaian, R., Oniga, O. (2018). “Tiperciuc Antibacterial evaluation and virtual screening of new thiazolyl-triazole Schiff bases as potential DNA-gyrase inhibitors”, Int. J. Mol. Sci., 19, 222.
• Özdemir, G. (2016). “Synthesis, characterization and investigation of some properties of some new 4-[3-methoxy-4-(benzensulfonyloxy)benzylidene amino]-4,5-dihydro-1H-1,2,4-triazol-5-on derivatives”, Master's Thesis, Kafkas University Institute of Science and Technology, Kars.
• Özsen, İ. (2010). “Synthesis, characterization and antibacterial activities of some new Schiff bases with diamines and their metal complexes”, Master's Thesis, Gazi University Institute of Science and Technology, Ankara.
• Pişkin, N. (2011). “New aminoacid -schiff bases and Ni(II) complexes synthesis, characterization and evaluation of biological activity”, Master's Thesis, Gazi University Institute of Science and Technology, Ankara. Tuncer, S., Akova, M. (1997). “Pseudomonas aeruginosa İnfeksiyonları”. Flora, 1,61-65.
• Turhan Irak, Z., & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi. Journal of the Institute of Science & Technology, 9(1), 512-521.
• Uğurlu G., & Beytur, M. (2020). Theoretical Studies on The Structural, Vibrational, Conformational Analysis and Nonlinear Optic (NLO) Property of 4-(Methoxycarbonyl) Phenylboronic Acid. Indian Journal of Chemistry-Section A, 59(10), 1504-1512.
• Yüksek, H. Göksu, B., Manap, S., Beytur, M. & Gürsoy Kol, Ö. (2018). Synthesis of some new 4-[2-(2-methylbenzoxy)-benzylidenamino]-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives with their antioxidant properties, Chemical Science International Journal, 22(2), 1- 29.
• Zeydan, C., (2009). “Synthesis of schiff bases obtained from 1,2,4-triazole-3-thione and evaluation of their biological activities”, Master's Thesis, Marmara University, Institute of Health Sciences, İstanbul.