Some New Bis-(1,2,4-Triazole) Compounds: Synthesis, Characterization and Urease Enzyme Inhibition
Abstract
In this study, thiosemicarbazide derivatives (2a-c) were obtained from the reaction of acetohydrazide derivative 1,2,4-triazole compound (1) with methyl isothiocyanate, phenyl isothiocyanate, and 4-methylphenyl isothiocyanate compounds, respectively. Then, by intramolecular cyclization of 2a-c compounds, bis-(1,2,4-triazole) compounds (3a-c) were synthesized. The synthesized compounds' chemical structures were verified using FT-IR, 1H-NMR, and 13C-NMR spectroscopic methods. In addition, the urease enzyme inhibition of the synthesized compounds was evaluated using the Weatherburn method in vitro. All newly synthesized compounds showed urease enzyme inhibition in the range of 15.00 ± 0.10 to 16.00 ± 0.25 IC50 (µg/mL) compared to standard thiourea (IC50 = 15.75 ± 0.15 µg/mL).
Keywords
Bis-(1,2,4-triazole), Isothiocyanate, Thiosemicarbazide, Urease
Supporting Institution
no
Project Number
yok
Ethical Statement
no
Thanks
no
References
- Amir, M., and Shikha, K. (2004). Synthesisand Anti-inflammatory, Analgesic, Ulserogenic and Lipid Peroxidation Activities of Some New 2-[(2,6-Dichloroanilino)phenyl]acetic Acid Derivatives. European Journal of Medicinal Chemistry, 39, 535–545.
- Akyüz, G., Emirik, M.,, Sökmen, B. B., and Menteşe, E. (2022). Synthesis and Docking Studies of Novel Benzimidazole Derivatives Containing Thiophene and Triazole Rings as Potential Urease Inhibitors. Russian Journal of Bioorganic Chemistry, 48, 87–95.
- Akyuz, G., and Mentese, E. (2023). Synthesis of New Coumarin-C3 Benzimidazole Hybrids and Their Urease Inhibition Studies. Letters in Organic Chemistry, 20, 9, 864–870.
- Bentley, A., Butters, M.S., Green, P., Learmonth, W. J., MacRae, J. A., Morland, M. C. G., Connor, O., and Skuse, J. (2002). The Discovery and Process Development of a Commercial Routeto the Water-Soluble Prodrug, Fosfluconazole. Organic Process Research& Development, 6, 109–112.
- Bekhit, A. A., El-Sayed, O. A., Aboulmagd, E., and Park, J. Y. (2004). Tetrazolo[1,5- a] quinoline as a potential promising new scaff old forthe synthesis of novel antiinflammatory and antibacterial agents. European Journal of Medicinal Chemistry, 39, 249–255.
- El-Khawass, S. D. M., and Habib, N. S. (1989). Synthesis of 1,2,4-triazole, 1,2,4-triazolo[3,4- b][1,3,4]thiazinederivatives of benzotriazole. Journal of Heterocyclic Chemistry, 26, 177–181.
- Farghaly, A. M., Bekhit, A. A., and Park, J. Y. (2000). Design and synthesis of some oxadiazolyl, thiadiazolyl, thiazolidinyl, and thiazolylderivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Archiv der Pharmazie, 333, 53–57.
- Gupta, A., Unadkat, J. D., and Mao, Q. (2007). Interactions of Azole Antifungal Agents with theHuman Breast Cancer Resistance Protein (BCRP). Journal of Pharmaceutical Science, 96, 3226–3235.
- Kahveci, B., Yılmaz, F., Menteşe, E., and Ülker, S. (2015). Microwave-assistedsynthesis of some new coumarin derivativesin cluding 1,2,4-triazol-3-one and investigation of their biological activities. Chemistry of Heterocyclic Compounds, 51, 5, 447–456.
- Karaali, N. and Mentese, E. (2016). Synthesis and Study of Antitumor Activity of Some New 2-(4-Methoxybenzyl)-1H-Benzimidazole Derivatives Bearing Triazole, Oxadiazole and Ethanol Moiety. Revue Roumaine De Chimie, 61, 3, 187–192.
