Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities
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.
___
- 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-Dibenzoa,dcycloheptene 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.