Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities

Year 2019, Volume: 47 Issue: 3, 277 - 286, 23.10.2019

Zeynep Özdemir , İnci Selin Doğan Mehmet Abdullah Alagöz Hasan Erdinç Sellitepe , Didem Kart

https://doi.org/10.15671/hjbc.626966

Abstract

I
n this study, four new oxime ether derivatives were synthesized and their antimicrobial activities were evaluated. At the
same time, a comparison of the efficiency of the conventional method of synthesis with the microwave method was investigated. The structures of synthesized compounds were confirmed by their IR, 1H-NMR, and HRMS spectra. Antimicrobial
activity of the compounds was tested against two Gr (+) bacteria (S. aureus, E. faecalis), two Gr (-) bacteria (P. aeruginosa, E.
coli), and three yeast-like fungi (C. albicans, C. krusei, C. parapsilosis) by modified agar dilution method.

Keywords

Triazole, oxime ether, microwave synthesis, antimicrobial activity

References

• 1. A.S. Hassan, D.M. Masoud , F.M. Sroor , A.A. Askar, Synthesis and biological evaluation of pyrazolo[1,5-a]pyrimidine-3- carboxamide as antimicrobial agents, Med. Chem. Res., 26 (2017) 2909-2919.
• 2. I. Roca, M. Akova, F. Baquero, J. Carlet, M. Cavaleri, S. Coenen, J. Cohen, D. Findlay, I. Gyssens, O.E. Heure, G. Kahlmeter, The global threat of antimicrobial resistance: science for intervention, New Microbes New Infect., 6 (2015) 22-29.
• 3. M.A. Abdelrahman, I. Salama, M.S. Gomaa, M.M. Elaasser, M.M. Abdel-Aziz, D.H. Soliman, Design, synthesis and 2D QSAR study of novel pyridine and quinolone hydrazone derivatives as potential antimicrobial and antitubercular agents, Eur. J. Med. Chem., 138 (2017) 698-714.
• 4. S. Silva, M. Negri, M. Henriques, R. Oliveira, D.W. Williams, J. Azeredo, Candida glabrata, Candida parapsilosis and Candida tropicalis: biology, epidemiology, pathogenicity and antifungal resistance, FEMS Microbiol. Rev., 36/2 (2012) 288-305.
• 5. M. Janeczko, O.M. Demchuk, D. Strzelecka, K. Kubinski, M. Masłyk, New family of antimicrobial agents derived from 1,4-naphthoquinone., Eur. J. Med. Chem., 124 (2016) 1019- 1025.
• 6. S. Concilio, L. Sessa, A.M. Petrone, A. Porta, R. Diana, P. Iannelli, S. Piotto, Structure Modification of an Active AzoCompound as a Route to New Antimicrobial Compounds, Molecules, 22 (2017) 875.
• 7. A. Karakurt, M.D. Aytemir, J.P. Stables, M. Özalp, F.B. Kaynak, S. Özbey, S. Dalkara, Synthesis of some oxime ether derivatives of 1-(2-naphthyl)-2-(1,2,4-triazol-1-yl)ethanone and their anticonvulsant and antimicrobial activities, Arch. Pharm. (Weinheim, Germany), 339 (2006) 513-520.
• 8. S. Kaping, I. Boiss, L.I. Singha, P. Helissey, J.N. Vishwakarma, A facile, regioselective synthesis of novel 3-(N-phenylcarboxamide)pyrazolo[1,5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their antibacterial activities, Mol. Divers., 20 (2016) 379–390.
• 9. S. Deshmukh, K. Dingore, V. Gaikwad, M. Jachak, An efficient synthesis of pyrazolo[1,5-a]pyrimidines and evaluation of their antimicrobial activity, J Chem. Sci., 128 (2016) 1459– 1468.
• 10. J. Zhang, J.F. Peng, T. Wang, P. Wang, Z.T. Zhang, Synthesis, crystal structure, characterization and antifungal activity of pyrazolo[1,5-a]pyrimidines derivatives, J. Mol. Struct., 1120 (2016) 228–233.
• 11. A.N. Ambhore, R.D. Kamble, P.P. Mogle, S.V. Hese, S.N. Kadam, M.J. Hebade, S.S. Kamble, R.N. Gacche, B.S. Dawane1, An Efficient One-pot Synthesis of some New Pyrazolyl Appended 1,3,4-Oxadiazole Derivatives as Antibacterial and Antioxidant agents, Der. Pharma. Chemica, 9/9 (2017) 48-56.
• 12. Z. Özdemir, A. Karakurt, Ü. Çalış, S. Günal, Ş. Işık, Z.S. Şahin, S. Dalkara, Synthesis, anticonvulsant and antimicrobial activities of some new[1-(2-naphthyl)-2(pyrazol-1-yl) ethanone]oximeethers, Med. Chem., 11 (2015) 41–49.
• 13. A. Karakurt, S. Dalkara, M. Özalp, S. Özbey, E. Kendi, J.P. Stables, Synthesis of some 1-(2-naphthyl)-2-(imidazole-1- yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities, Eur. J. Med. Chem., 36 (2001) 421-33.
• 14. İ.S. Doğan, S. Saraç, S. Sari, D. Kart, G.Ş. Eşsiz, İ. Vural, S. Dalkara, New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies, Eur. J. Med. Chem., 21/130 (2017) 124-138.
• 15. A. Karakurt, M.A. Alagöz, B. Sayoğlu, Ü. Calış, S. Dalkara, Synthesis of some novel 1-(2-naphthyl)-2-(imidazol-1-yl) ethanone oxime ester derivatives and evaluation of their anticonvulsant activity, Eur. J. Med. Chem., 57 (2012) 275- 282.
• 16. M. Larhed, A. Hallberg, Microwave-assisted high-speed chemistry: a new technique in drug discovery, Drug Discov. Today, 6/8 (2001) 406-416.
• 17. P. Lidström, J. Tierney, B. Wathey, J. Westman, Microwave assisted organic synthesis-a review, Tetrahedron, 57 (2001) 9225-9283.
• 18. B.L. Hayes, Recent Advances in Microwave-Assisted Synthesis, Aldrichimica Acta, 37 (2004) 66-76.
• 19. S. Balalaie, M.M. Hashemi, M. Akhbari, A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation, Tetrahedron Lett., 44 (2003) 1709–1711.
• 20. T. Immediata, A.R. Day, Beta-Naphtyl Derivatives of Ethanolamine and N-Substituted Ethanolamines, J. Org. Chem., 5 (1940) 512-27.
• 21. Ü. Çalış, S. Dalkara, M. Ertan, R. Sunal, The Significance of the Imidazole Ring in Anticonvulsant Activity of (Arylalkyl) imidazoles, Arch. Pharm. (Weinheim), 321 (1988) 841-846.
• 22. F. Özkanlı, S. Dalkara, Ü. Çalış, A. Willke, Synthesis of Some N-Arylazole Acetamide Derivatives and Their Anticonvulsant and Antimicrobial Activities, ArzneimmittelForsch., 44/8 (1994) 920-924.
• 23. Clinical and Laboratory Standards Institute, Approved StandardSeventh Edition, CLSI Document M7-A7, Pennsylvania, https://www.clsi.org/media/1632/m07a10_ sample.pdf, 2003 (accessed 24.05.2018)
• 24. Clinical and Laboratory Standards Institute, Approved StandardSecond Edition. NCCLS document M27-A2, Pennsylvania, 2002.
• 25. J. Gootjes, A.B.H. Funcke, H. Timmerman, W.TH. Nauta, Experiments in the 5H-Dibenzoa,dcycloheptene Series, ArzneimmittelForsch., 22/12 (1972) 2070-2073.
• 26. E. Pretsch, T. Clerk, J. Seibl, W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer- Verlag, Berlin, 1983.