Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities

Hacer Bayrak; Yıldız Uygun Cebeci

doi:10.31466/kfbd.620635

TR EN

Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities

Abstract

In this study, antipyrine (4-aminoantipyrine) was selected as the starting material and anti-tubercular activities were compared by carrying out the antipyrine nucleated carbothioamide and 1,2,4-triazole derivatives. The treatment of 4-aminoantipyrine with ethylbromoacetate, hydrazinhydrate and various iso (thio) cyanates, respectively, followed by cyclic reaction by basic reaction resulted in the addition of a second ring of 1,2,4-triazole to the structure. The structures of the synthesized new antipyrine derivatives were determined by spectroscopic methods such as IR, NMR and mass spectrophotometry. For the new compounds synthesized, activity studies were performed against non-Gram bacteria.

Keywords

Antipyrine, 1 2 4-Triazole, Anti-tubercular Activity

Supporting Institution

Karadeniz Teknik Üniversitesi Bilimsel Araştırma Projesi (KTÜ-BAP)

Project Number

5289

Thanks

This work was supported by the Scientific research project of Karadeniz Technical University (KTU-BAP) [grant numbers 5289]. The author also thanks to Prof. Şengül Alpay Karaoğlu for the antitubercular activity studies.

References

Abdel-Latif, E., (2006). Phosphorus, Sulfur Silicon Relat. Elem., 181, 125-139.
Abu-Elmaati, T.M., (2002). Acta Chim. Slov., 49, 721-732.
Bondock, S., Rabie, R., Etman, H.A. and Fadda, A.A., (2008). Eur. J. Med. Chem., 43, 2122-2129.
Chandra, J. N. N. S., Sadashiv, C.T., Kavitha, C.V. and Rangappa, K.S., (2006). Bioorg. Med. Chem., 14, 6621-27.
Demirbaş, N. and Uğurluoğlu, R., (2004). Turk J. Chem., 28, 559-570.
Demirbaş, N., Uğurluoğlu, R. and Demirbas, A., (2002). Bioorg. Med. Chem., 10, 3717-3723.
Dixit, P.P., Patil, V.J., Nair, P.S., Jain, S., Sinha, N. and Arora, S.K., (2006). Eur. J. Med. Chem., 41, 423-28.
Filho, V.C., Correa, Z., Vaz, J.B., Calixto, R.J., Nunes, T.R., Pinheiro, A.D. and Andricopulo, R.A., (1998). Il Framaco, 53, 55-57.
Gürsoy, A., Demirayak, S., Capan, G., Erol, K. and Vurual, K., (2000). Eur. J. Med. Chem., 35, 359-364.
Holla, B., S., Sarojini, B., K., Sooryanarayana, R., Akberali, P., M., Kumari, N., S. and Shetty, V., (2001). II Farmaco, 56, 565-570.

İkizler, A., Demirbaş, N. and İkizler, A., (1996). J Het. Chem., 33, 1765-69.
İkizler, A.A., Ucar, F.I., Demirbaş, N.D., Yasa, I., Demirbaş, A. and Genzer, T., (1999). Indian j. Pharm. Sci., 61, 271-74.
İsmail, M.M.F., Ammar, Y.A., El-Zahaby, H.S.A., Eisa, S.I. and Barakat, S.E., (2007). Arch. Pharm. Life Sci., 340, 476-482.
Jain, S.C., Sinha, J., Bhagat, S., Errington, W. and Olsen, C.E., (2003). Synth. Commun., 33, 563-577.
Kolavi, G., Hedge, V., Khazi, I, A. and Gadad, P., (2006). Bioorg. Med. Chem., 14, 3069-3080.
Mishra, A.P., (1999). J. Indian Chem. Soc., 76, 35-37.
Raman, N., Kulandaisamy, A. and Jeyasubramanian, K., (2002). Synth. React. Inorg. Met., 32, 1583-1610.
Raman, N., Kulandaisamy, A. and Jeyasubramanian, K., (2004). Synth. React. Inorg. Met., 34, 17-43.
Rostom, S.A.F., El-Ashmawy, I.M., Abd El Razik, H.A., Badr, M.H. and Ashour, H.M.A., (2009). Bioorg. Med. Chem., 17, 882-895.
Rostom, S., A., F., Shalaby, M., A. and El-Demellawy, A., (2003). Eur. J. Med. Chem., 38, 959-974.
Sondhi, S.M., Sharma, V.K., Verma, R.P., Singhal, N., Shukla, R., Raghubir, R. and Dubey, M.P., (1999). Synthesis, 878-884.
Sondhi, S.M., Singhal, N., Verma, S.K., Arora, S.K. and Dastidar, S.G., (2001). Indian J. Chem., Sect. B, 40, 113-119.
Sun, S., Lou, H., Gao, Y., Fan, P., Ma, B., Ge, W. and Wang, X., (2004). Journal of Pharmaceutical and Biomedical Analysis, 34, 1117-1124.
Turan-Zitouni, G., Kaplancikli, Z., A., Erol, K. and Kilic, F., S., (1999). II Farmaco, 54, 218-223.
Turan-Zitouni, G., Sivaci, M., Kilic, F.S.and Erol, K., (2001). Eur. J. Med. Chem., 36, 685-689.
Verrect, G., Six, K., Mooter, G. V., Baert, L., Peeters, J. and Brewser, M. E., (2003). International Journal of Pharmaceutics, 251, 165-174.
Woods, G.L., Brown-Elliott, B.A., Desmond, E.P., Hall, G.S., Heifets, L., Pfyffer, G.E., Ridderhof, J.C., Wallace, R.J., Jr. Warren, N.C. and Witebsky, F.G., (2003). Approved Standard. NCCLS document M24-A, 23, 18.

Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Hacer Bayrak ^*
0000-0001-5843-8716
Türkiye

Yıldız Uygun Cebeci This is me
0000-0001-7949-0329
Türkiye

Publication Date

December 15, 2019

Submission Date

September 16, 2019

Acceptance Date

December 13, 2019

Published in Issue

Year 2019 Volume: 9 Number: 2

DOI

https://doi.org/10.31466/kfbd.620635

IZ

https://izlik.org/JA49CD94SZ

APA

Bayrak, H., & Uygun Cebeci, Y. (2019). Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities. Karadeniz Fen Bilimleri Dergisi, 9(2), 323-334. https://doi.org/10.31466/kfbd.620635

AMA

1.Bayrak H, Uygun Cebeci Y. Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities. KFBD. 2019;9(2):323-334. doi:10.31466/kfbd.620635

Chicago

Bayrak, Hacer, and Yıldız Uygun Cebeci. 2019. “Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-Tubercular Activities”. Karadeniz Fen Bilimleri Dergisi 9 (2): 323-34. https://doi.org/10.31466/kfbd.620635.

EndNote

Bayrak H, Uygun Cebeci Y (December 1, 2019) Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities. Karadeniz Fen Bilimleri Dergisi 9 2 323–334.

IEEE

[1]H. Bayrak and Y. Uygun Cebeci, “Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities”, KFBD, vol. 9, no. 2, pp. 323–334, Dec. 2019, doi: 10.31466/kfbd.620635.

ISNAD

Bayrak, Hacer - Uygun Cebeci, Yıldız. “Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-Tubercular Activities”. Karadeniz Fen Bilimleri Dergisi 9/2 (December 1, 2019): 323-334. https://doi.org/10.31466/kfbd.620635.

JAMA

1.Bayrak H, Uygun Cebeci Y. Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities. KFBD. 2019;9:323–334.

MLA

Bayrak, Hacer, and Yıldız Uygun Cebeci. “Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-Tubercular Activities”. Karadeniz Fen Bilimleri Dergisi, vol. 9, no. 2, Dec. 2019, pp. 323-34, doi:10.31466/kfbd.620635.

Vancouver

1.Hacer Bayrak, Yıldız Uygun Cebeci. Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities. KFBD. 2019 Dec. 1;9(2):323-34. doi:10.31466/kfbd.620635

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Synthesis, In Silico Studies, Antimicrobial, Antioxidant Activities, Docking Simulation, and Computational Analysis of Novel Acrylamide Derivatives

Russian Journal of General Chemistry

https://doi.org/10.1134/S1070363224080188

The published articles in The Black Sea Journal of Sciences are licensed under Creative Commons Attribution-NonCommercial 4.0 International

Bazı Yeni Antipirin Karbo (tiyo) amid ve 1,2,4-Triazol Türevlerinin Sentezi ve Anti-tuberküler Aktivitelerinin Karşılaştırılması

Abstract

Keywords

Project Number

Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities

Abstract

Keywords

Supporting Institution

Project Number

Thanks

References

Details

Primary Language

Subjects

Journal Section

Authors

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite

Cited By

Synthesis, In Silico Studies, Antimicrobial, Antioxidant Activities, Docking Simulation, and Computational Analysis of Novel Acrylamide Derivatives