Synthesis of Some New Kind of Antipyrine Carbo(thio)amide and 1,2,4-Triazole Derivatives and Comparing Their Anti-tubercular Activities
Yıl 2019,
Cilt: 9 Sayı: 2, 323 - 334, 15.12.2019
Hacer Bayrak
,
Yıldız Uygun Cebeci
Öz
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.
Destekleyen Kurum
Karadeniz Teknik Üniversitesi Bilimsel Araştırma Projesi (KTÜ-BAP)
Teşekkür
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.
Kaynakça
- 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.
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- 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.
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- 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
Yıl 2019,
Cilt: 9 Sayı: 2, 323 - 334, 15.12.2019
Hacer Bayrak
,
Yıldız Uygun Cebeci
Öz
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.
Kaynakça
- 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.