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

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

doi:10.15671/hjbc.626966

Araştırma Makalesi

Yıl 2019, Cilt: 47 Sayı: 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

Öz

Kaynakça

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.

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

Yıl 2019, Cilt: 47 Sayı: 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

Öz

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.

Anahtar Kelimeler

Triazole, oxime ether, microwave synthesis, antimicrobial activity

Kaynakça

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.

Toplam 26 adet kaynakça vardır.

Ayrıntılar

Birincil Dil	İngilizce
Bölüm	Articles
Yazarlar	Zeynep Özdemir İnci Selin Doğan Bu kişi benim Mehmet Abdullah Alagöz Bu kişi benim Hasan Erdinç Sellitepe Bu kişi benim Didem Kart Bu kişi benim
Yayımlanma Tarihi	23 Ekim 2019
Kabul Tarihi	27 Mayıs 2019
Yayımlandığı Sayı	Yıl 2019 Cilt: 47 Sayı: 3

Kaynak Göster

APA	Özdemir, Z., Doğan, İ. S., Alagöz, M. A., Sellitepe, H. E., vd. (2019). Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities. Hacettepe Journal of Biology and Chemistry, 47(3), 277-286. https://doi.org/10.15671/hjbc.626966
AMA	Özdemir Z, Doğan İS, Alagöz MA, Sellitepe HE, Kart D. Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities. HJBC. Ekim 2019;47(3):277-286. doi:10.15671/hjbc.626966
Chicago	Özdemir, Zeynep, İnci Selin Doğan, Mehmet Abdullah Alagöz, Hasan Erdinç Sellitepe, ve Didem Kart. “Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities”. Hacettepe Journal of Biology and Chemistry 47, sy. 3 (Ekim 2019): 277-86. https://doi.org/10.15671/hjbc.626966.
EndNote	Özdemir Z, Doğan İS, Alagöz MA, Sellitepe HE, Kart D (01 Ekim 2019) Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities. Hacettepe Journal of Biology and Chemistry 47 3 277–286.
IEEE	Z. Özdemir, İ. S. Doğan, M. A. Alagöz, H. E. Sellitepe, ve D. Kart, “Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities”, HJBC, c. 47, sy. 3, ss. 277–286, 2019, doi: 10.15671/hjbc.626966.
ISNAD	Özdemir, Zeynep vd. “Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities”. Hacettepe Journal of Biology and Chemistry 47/3 (Ekim 2019), 277-286. https://doi.org/10.15671/hjbc.626966.
JAMA	Özdemir Z, Doğan İS, Alagöz MA, Sellitepe HE, Kart D. Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities. HJBC. 2019;47:277–286.
MLA	Özdemir, Zeynep vd. “Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities”. Hacettepe Journal of Biology and Chemistry, c. 47, sy. 3, 2019, ss. 277-86, doi:10.15671/hjbc.626966.
Vancouver	Özdemir Z, Doğan İS, Alagöz MA, Sellitepe HE, Kart D. Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities. HJBC. 2019;47(3):277-86.

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