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

Year 2019, Volume: 9 Issue: 2, 323 - 334, 15.12.2019
https://doi.org/10.31466/kfbd.620635

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.

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.

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

Year 2019, Volume: 9 Issue: 2, 323 - 334, 15.12.2019
https://doi.org/10.31466/kfbd.620635

Abstract

Bu
çalışmada antipirin (4-Aminoantipirin) başlangıç maddesi olarak seçilerek
karbotiyoamit ve 1,2,4-triazoltürevi bileşikler gerçekleştirilerek anti-tuberküler
aktiviteleri karşılaştırılmıştır. 4-aminoantipirin sırasıyla etilbromoasetat,
hidrazinhidrat ve çeşitli izo(tiyo)siyanatlar ile muamelesi sonucu bazik
ortamda reaksiyonu ile halkalaşma reaksiyonu gerçekleşmesi ile yapıya ikinci
bir halka olan 1,2,4-triazol halkasının ilavesi gerçekleştirildi. Sentezlenen
yeni antipirin türevi bileşiklerin yapıları IR, NMR ve kütle spektrofotometresi
gibi spektroskopik yöntemlerle aydınlatıldı. Sentezlenen yeni bileşikler, Gram
olmayan bakteriye karşı aktivite çalışmaları gerçekleştirilmiştir. 

Project Number

5289

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.
There are 27 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Hacer Bayrak 0000-0001-5843-8716

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

Project Number 5289
Publication Date December 15, 2019
Published in Issue Year 2019 Volume: 9 Issue: 2

Cite

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