Abstract
A series of 1,2,4-triazol-3-one derivatives were synthesized by using conventional heating and microwave irradiation techniques. Microwave syntheses of the target compounds were carried out by using both a domestic microwave oven and a monomode microwave reactor. The results showed that the use of microwave technique is advantageous in terms of time, low solvent loading, yield, and efficiency. The synthesized compounds were tested for their antioxidant and antiurease activities. The antioxidant activity was evaluated by using ABTS [2,2′-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt] radical scavenging and cupric ion reducing antioxidant capacity (CUPRAC) methods. Most of the compounds showed good antioxidant activity, especially compound 8d showed an SC50 value of 71.062±9.31 μM in comparison to Trolox used as standard (SC50 = 210.04±16.22 μM). According to the urease inhibitory activity results, most of the compounds showed better activity than thiourea (IC50 = 0.5027±0.0293 μM); in particular, compound 8a exhibited an IC50 value of 0.3070±0.0394 μM.
REFERENCES
Kappe, C.O., Angew. Chem., Int. Ed., 2004, vol. 43, p. 6250. https://doi.org/10.1002/anie.200400655
Kappe, C.O. and Dallinger, D., Nat. Rev. Drug Discovery, 2006, vol. 5, p. 51. https://doi.org/10.1038/nrd1926
Kahveci, B., Yilmaz, F., Menteşe, E., and Beriş, F.Ş., J. Chem. Res., 2012, vol. 36, p. 484. https://doi.org/10.3184/174751912X13400138806685
Özil, M., Emirik, M., Etlik, S.Y., Ülker, S., and Kahveci, B., Bioorg. Chem., 2016, vol. 68, p. 226. https://doi.org/10.1016/j.bioorg.2016.08.011
Özil, M., Menteşe, E., Yilmaz, F., Islamoǧlu, F., and Kahveci, B., J. Chem. Res., 2011, vol. 35, p. 268. https://doi.org/10.3184/174751911X13043524455143
Kahveci, B., Yilmaz, F., Menteşe, E., and Ülker, S., Chem. Heterocycl. Compd., 2015, vol. 51, p. 447. https://doi.org/10.1007/s10593-015-1714-5
Kahveci, B., Özil, M., Menteşe, E., Bekircan, O., and Buruk, K., Russ. J. Org. Chem., 2008, vol. 44, p. 1816. https://doi.org/10.1134/S1070428008120178
Kahveci, B., Menteşe, E., Akkaya, E., Yilmaz, F., Doǧan, I.S., and Özel, A., Arch. Pharm. (Weinheim, Ger.), 2014, vol. 347, p. 449. https://doi.org/10.1002/ardp.201300427
Ding, Z., Zhou, M., and Zeng, C., Arch. Pharm. (Weinheim, Ger.), 2020, vol. 353, article ID 1900367. https://doi.org/10.1002/ardp.201900367
Dar, O.A., Lone, S.A., Malik, M.A., Aqlan, F.M., Wani, M.Y., Hashmi, A.A., and Ahmad, A., Heliyon, 2019, vol. 5, article ID e02055. https://doi.org/10.1016/j.heliyon.2019.e02055
Brandão, P., Marques, C., Burke, A.J., and Pineiro, M., Eur. J. Med. Chem., 2021, vol. 211, article ID 113102. https://doi.org/10.1016/j.ejmech.2020.113102
Raju, R., Chidambaram, K., Chandrasekaran, B., Bayan, M.F., Kumar Maity, T., Alkahtani, A.M., and Chandramoorthy, H.C., J. Saudi Chem. Soc., 2023, vol. 27, article ID 101598. https://doi.org/10.1016/j.jscs.2023.101598
Andreani, A., Burnelli, S., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Varoli, L., Cremonini, M.A., Placucci, G., Cervellati, R., and Greco, E., Eur. J. Med. Chem., 2010, vol. 45, p. 1374. https://doi.org/10.1016/j.ejmech.2009.12.035
Elsaman, T., Mohamed, M.S., Eltayib, E.M., Abdelaziz, H.A., Abdalla, A.E., Munir, M.U., and Mohamed, M.A., Med. Chem. Res., 2022, vol. 31, p. 244. https://doi.org/10.1007/s00044-021-02832-4
De Moraes Gomes, P.A.T., Pena, J.L., and Leite, C.L.A., Mini-Rev. Med. Chem., 2019, vol. 19, p. 56. https://doi.org/10.2174/1389557518666180424093305
Xie, C., Tang, L.-M., Li, F.-N., Guan, L.-P., Pan, C.-Y., and Wang, S.-H., Med. Chem. Res., 2014, vol. 23, p. 2161. https://doi.org/10.1007/s00044-013-0811-1
Ceramella, J., Iacopetta, D., Catalano, A., Cirillo, F., Lappano, R., and Sinicropi, M.S., Antibiotics, 2022, vol. 11, p. 191. https://doi.org/10.3390/antibiotics11020191
Pandeya, S.N., Sriram, D., Nath, G., and DeClercq, E., Eur. J. Pharm. Sci., 1999, vol. 9, p. 25. https://doi.org/10.1016/S0928-0987(99)00038-X
Smolyaninov, I.V., Burmistrova, D.A., Arsenyev, M.V., Almyasheva, N.R., Ivanova, E.S., Smolyaninova, S.A., Pashchenko, K.P., Poddel’sky, A.I., and Berberova, N.T., ChemistrySelect, 2021, vol. 6, p. 10609. https://doi.org/10.1002/slct.202102246
Ohshima, A., Momotake, A., and Arai, T., J. Photochem. Photobiol., A, 2004, vol. 162, p. 473. https://doi.org/10.1016/S1010-6030(03)00388-5
Kahveci, B., Molecules, 2005, vol. 10, p. 376. https://doi.org/10.3390/10020376
Kahveci, B., Yılmaz, F., Menteşe, E., and Ülker, S., Arch. Pharm. (Weinheim, Ger.), 2017, vol. 350, article ID 1600379. https://doi.org/10.1002/ardp.201600369
Milcent, R. and Redeuilh, C., J. Heterocycl. Chem., 1979, vol. 16, p. 403. https://doi.org/10.1002/jhet.5570160245
İkizler, A.A., İkizler, A., and Yıldırım, N., Monatsh. Chem., 1991, vol. 122, p. 557. https://doi.org/10.1007/BF00809810
Apak, R., Güçlü, K., Özyürek, M., and Karademir, S.E., J. Agric. Food Chem., 2004, vol. 52, p. 7970. https://doi.org/10.1021/jf048741x
Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., and Rice-Evans, C., Free Radicals Biol. Med., 1999, vol. 26, p. 1231. https://doi.org/10.1016/S0891-5849(98)00315-3
Menteşe, E., Emirik, M., and Sökmen, B.B., Bioorg. Chem., 2019, vol. 86, p. 151. https://doi.org/10.1016/j.bioorg.2019.01.061
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The author thanks the Department of Scientific Research Project of Recep Tayyip Erdogan University for financial assistance (project no. FBA-2021-1276).
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Yilmaz, F. Green Synthesis and Biological Evaluation of Some 1,2,4-Triazol-3-ones. Russ J Org Chem 60, 513–521 (2024). https://doi.org/10.1134/S1070428024030205
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DOI: https://doi.org/10.1134/S1070428024030205