Cu(II) complexes of 2-methoxy-5-sulfamoylbenzoic acid and 2-aminopyridine derivatives: Synthesis, characterization and antimicrobial activity

Year 2024, Volume: 8 Issue: 2, 153 - 158

Halil İlkimen , Cengiz Yenikaya , Aysel Gülbandılar

https://doi.org/10.32571/ijct.1368532

Abstract

Three novel mixed ligand Cu(II) complexes {[Cu(sba)2(X)2].2H2O, X = 2a3NO24mp for 1, 2a5Clp for 2, 2a5NO2p for 3} obtained from 2-methoxy-5-sulfamoylbenzoic acid (Hsba) with 2-amino-3-nitro-4-methylpyridine (2a3NO24mp), 2-amino-5-chloropyridine (2a5Clp) and 2-amino-5-nitropyridine (2a5NO2p), respectively, have been prepared. The structures of 1-3 FT-IR, AAS, UV, molar conductivity, magnetic susceptibility, and charge balance as suggested by previous studies have been characterized. According to spectroscopic findings, the structures of 1-3 can be postulated as tetrahedral complexes. Furthermore, all compounds have been screened for their antibacterial and antifungal activities against Pseudomonas aeruginosa (ATCC 27853), Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (NRRL B-767), Bacillus subtilis, Escherichia coli (ATCC25922) and Listeria monocytogenes (ATCC 7644) bacteria and Candida albicans (F89) yeast. The outcomes are contrasted with those of the control substances (Fluconazole as antifungal and Cefepime, Levofloxacin, and Vancomycin as antibacterial agents). The best activity values of the compounds are Cu(Ac)2.2H2O for S. aureus bacteria, 2a5NO2p for E. coli bacteria, 2 for P. aeruginoa bacteria, Hsba, 2a3NO24mp and 2a5NO2p for L. monocytogenes bacteria, Cu(Ac)2.2H2O, 2a3NO24mp, 2a5Clp, 2a5NO2p and 2 for E. faecalis bacteria, all compounds (except 3) for B. subtilis bacteria, and 2a5NO2p and 1 were observed for C. albicans yeast.

Keywords

2-Methoxy-5-sulfamoylbenzoic acid, aminopyridine, Cu(II) metal complex, antifungal activity, antibacterial activity

Project Number

The authors acknowledge the support provided by Kütahya Dumlupınar University Research Fund (Grant No. 2020/02).

Thanks

The authors acknowledge the support provided by Kütahya Dumlupınar University Research Fund (Grant No. 2020/02).

References

• 1. Marinescu, M. Int. J. Pharm. Bio. Sci. 2017, 8(2), 338-355.
• 2. Garcia-Raso, A.; Fiol, J.J.; Lopez-Zafra, A.; Cabrero, A.; Mata, I.; Molins, E. Polyhedron, 1999, 18(6), 871-878.
• 3. Lechat, P.; Tesleff, S.; Bownan, W.C. Aminopyridines and similarly acting drugs, Pergamon, Oxford, 1982.
• 4. Yenikaya, C.; Poyraz, M.; Sarı, M.; Demirci, F.; İlkimen, H.; Bülbül, M.; Büyükgüngör, O. Polyhedron, 2009, 28, 3526-3532.
• 5. Yenikaya, C.; Büyükkıdan, N.; Sarı, M.; Kesli, R.; İlkimen, H.; Bülbül, M.; Büyükgüngör, O. J. Coord. Chem. 2011, 64, 3353-3365.
• 6. Pomarnacka, E.; Angielski, S.; Hoppe, A. Acta Polon. Pharm. 1984, 41(2), 141-151.
• 7. Petzinger, E. Deut. Tierar. Wochen. 1992, 99(10), 412-415.
• 8. Barroso, M.B.; Jimenez, R.M.; Alonso, R.M.; Ortiz, E. J. Chrom. B Ana. Tech. Biomed. Life Sci. 1996, 675(2), 303-312.
• 9. Lebedev, A.A.; Mironova L.I.; Pleshakov, M.G.; Malveeva, A.K.; Timokhina, I.A. Khim. Farm. Zhur. 1985, 19(10), 1205-1208.
• 10. Zhao, W.; Wang, J.; Ho, L.; Ono, K.; Teplow, D.B.; Pasinetti, G.M. J. Alzheimers Dis. 2009, 16, 49-57.
• 11. Tzin, V.; Galili, G. Mol. Plant. 2010, 3, 956-972.
• 12. Raymoni, G.; Ali, H.A. Appl. Organomet. Chem. 2018, 33(1), 46-80.
• 13. Mishra, C.B.; Kumari, S.; Angeli, A.; Bua, S.; Buonanno, M.; Monti, S.M.; Tiwari, M.; Supuran CT (2018) Euro. J. Med. Chem. 2018, 156, 430-443.
• 14. Zaksauskas, A.; Capkauskaite, E.; Jezepcikas, L.; Linkuviene, V.; Kisonaite, M.; Smirnov, A.; Manakova, E.; Grazulis, S.; Daumantas, M. Euro. J. Med. Chem. 2018, 156, 61-78.
• 15. Lykke, K.; Tollner, K.; Romermann, K.; Feit, P.W.; Erker, T.; MacAulay, N.; Loscher, W. (2015) British J. Pharm. 2015, 172(18), 4469-4480.
• 16. Abo-Ashour, M.F.; Eldehna, W.M.; Nocentini, A.; Ibrahim, H.S.; Bua, S.; Abou-Seri, S.M.; Supuran, C.T. Euro. J. Med. Chem. 2018, 157, 28-36.
• 17. Yenikaya, C.; Sarı, M.; Bülbül, M.; İlkimen, H.; Çelik, H.; Büyükgüngör, O. Bioorg. Med. Chem. 2010, 18, 930-938.
• 18. Yenikaya, C.; Sarı, M.; Bülbül, M.; İlkimen, H.; Çınar, B.; Büyükgüngör, O. J. Enzyme Inhib. Med. Chem. 2011, 26(1), 104-114.
• 19. İlkimen, H.; Gülbandılar A. Kuwait J. Sci., 2023, 50(3A), 1-11.
• 20. İlkimen, H.; Gülbandılar A. Uşak Univ. J. Sci. Nat. Sci., 2024, 8(1), 1-14.
• 21. İlkimen, H.; Yenikaya, C.; Gülbandılar, A. Selcuk Uni. Fac. Sci. J. Sci. 2023, 49(2), 53-63.
• 22. İlkimen, H.; Türken, N.; Gülbandılar, A. J. Iran. Chem. Soc. 2021, 18, 1941–1946.
• 23. İlkimen, H.; Gülbandılar, A. Synthesis, characterization and investigation of antimicrobial and antifungal activities of proton transfer salts of 2-amino-5-substitutedpiridin derivatives and 2-methoxy-5-sulfamoylbenzoic acid. 2nd International Conference on Contemporary Academic Research ICCAR, November 4-5 2023, Konya, Türkiye.
• 24. İlkimen, H.; Gülbandılar, A. Synthesis, characterization and investigation of antimicrobial and antifungal activities of 2-amino-6-substitutedpiridin derivatives and proton transfer salts of 2-methoxy-5-sulfamoylbenzoic acid. 2nd International Conference on Contemporary Academic Research ICCAR, November 4-5, 2023, Konya, Türkiye.
• 25. İlkimen, H.; Yenikaya, C.; Gülbandılar, A. Synthesis, characterization and investigation of antimicrobial and antifungal activities of 2-methoxy-5-sulfamoylbenzoic Acid and 2-Aminonitropyridine derivatives. 3rd International Conference on Innovative Academic Studies, September 26-28, 2023, Konya, Türkiye.
• 26. İlkimen, H.; Yenikaya, C.; Gülbandılar, A. Synthesis, characterization, antimicrobial and antifungal activities of 2-methoxy-5-sulfamoylbenzoic acid and 2-aminonitropyridine derivatives, 3rd International Conference on Innovative Academic Studies, September 26-28, 2023, Konya, Türkiye.
• 27. İlkimen, H.; Yenikaya, C.; Gülbandılar, A. Synthesis, characterization and investigation of antimicrobial properties of proton transfer salts and Cu(II) complexes of 2-methoxy-5-sulfamoylbenzoic acid and 2,3-diaminopyridine derivatives. III. Baskent International Conference On Multidisciplinary Studies, September 23-25, 2022, Ankara, Türkiye.
• 28. İlkimen, H.; Gülbandılar A. Pamukkale Univ. J. Engi. Sci., 2024, Doi. 10.5505/pajes.2024.48196.
• 29. İlkimen, H., Polyhedron, 2024, 257, 117019.
• 30. İlkimen, H. Macedonian J. Chem. Chemical Eng. 2019, 38(1), 13-17.
• 31. İlkimen, H.; Salün, S.G.; Yenikaya, C. Synthesis and characterization of metal complexes of 2-methoxy-5-sulfamoylbenzoic acid. SOCRATES 1st International Health, Engineering and Applied Sciences Congress. 19-20 June 2021, Ankara, Türkiye.
• 32. İlkimen, H.; Yenikaya, C.; Gülbandılar, A. Investigation of antimicrobial and antifungal activities of metal complexes of 2-metoxy-5-sulfamoylbenzoic acid, III. Baskent International Conference On Multidisciplinary Studies, September 23-25, 2022, Ankara, Türkiye.
• 33. Koneman, E.W.; Allen, S.D.; Winn, W.C. Colour Atlas and Textbook of Diagnostic Microbiology, Lippincott Raven Pub., Philadelphia, 1997, 122-30.
• 34. Nakamoto, K. Infrared and raman spectra of inorganic and coordination compounds, 5th ed., Wiley-Interscience, NewYork, p. 232, 1997.
• 35. Ucar, I.; Bulut, A.; Buyukgungor, O. J. Phys. Chem. Solids 2007, 68(12), 2271-2277.
• 36. Geary, W. J. Coord. Chem. Rev. 1971, 7, 81-122.