Yeni 1H-1,2,3-triazol türevleri: Sentez, Karakterizasyon ve Antioksidan Aktivite

Year 2025, Volume: 7 Issue: 2, 191 - 194, 31.05.2025

Fatih Çelik

https://doi.org/10.51435/turkjac.1681862

Abstract

4-bromo-N-(4-((1-(4-bromobenzil)-1H-1,2,3-triazol-4-il)metoksi)-3-metoksi benziliden) anilin (3), 2-((1-(3-(1,3-dioksoizoindolin-2-il) propil)-1H-1,2,3-triazol-4-il)metoksi) benzaldehit (6) ve 4-((1-(3-(1,3-dioksoizoindolin-2-il)propil) -1H-1,2,3-triazol-4-il)metoksi)-3-metoksibenzaldehit (8) sentezlendi. Bileşikler FTIR, 1H-NMR ve 13C-NMR spektroskopik yöntemleri ile karakterize edildi. Bileşiklerin antioksidan özellikleri yaygın olarak kabul görmüş iki metodoloji deneyi (DPPH ve FRAP) kullanılarak değerlendirildi. Bileşik 3, bileşikler arasında en yüksek antioksidan potansiyeline sahip olanıdır.

Keywords

antioxidant activity , sythesize , 1,2,3-triazol

New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity

Abstract

4-bromo-N-(4-((1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxy benzylidene) aniline (3), 2-((1-(3-(1,3-dioxoisoindolin-2-yl) propyl)-1H-1,2,3-triazol-4-yl)methoxy) benzaldehyde (6), and 4-((1-(3-(1,3-dioxoisoindolin-2-yl)propyl) -1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyben zaldehyde (8) were synthesized. The compounds were characterized by FTIR, 1H-NMR and 13C-NMR spectroscopic methods. The antioxidant properties of the compounds were evaluated using two widely accepted methodologies assays (DPPH and FRAP). Compound 3 has the highest antioxidant potential among the compounds.

Keywords

antioxidant activity , 1,2,3-triazol , sythesize

References

• F. Çelik, Y. Ünver, B. Barut, A. Özel, K. Sancak, Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry, Medicinal Chemistry, 2018, 230-241.
• E. Düğdü, D. Ünlüer, F. Çelik, K. Sancak, Ş. A. Karaoğlu, A. Özel, Synthesis of Novel Symmetrical 1,4-Disubstituted 1,2,3-Bistriazole Derivatives via ‘Click Chemistry’ and Their Biological Evaluation, Molecules, 21, 2019, 659-672.
• F. Çelik, F. Türkan, A. Aras, M. N. Atalar, H. S. Karaman, Y. Ünver, N. Kahriman, Synthesis of novel 1,2,3 Triazole Derivatives and Assessment of Their Potential Cholinesterases, Glutathione S-transferase Enzymes Inhibitory Properties: An in Vitro and in Silico Study, Bioorganic Chemistry, 107, 2021.
• R. P. Frutos, S. Rodriguez, N. D. Patel, D. Reeves, T. Tampone, C.H. Senanayake, A General and Practical Synthesis of N-Aryl-3- 4-(imidazol-4-yl)-1,2,3-triazol-1-yl benzamide Anti-Inflammatory Cytokine Inhibitors, Asian Journal of Organic Chemistry, 3, 2014, 769-772.
• R. Jain, P. Gahlyan, S. Dwivedi, R. Konwar, S. Kumar, M. Bhandari, R. Arora, R. Kakkar, R. Kumar, A.K. Prasad, Design, Synthesis and Evaluation of 1H-1,2,3-Triazol-4-yl-methyl Tethered 3-Pyrrolylisatins as Potent Anti-Breast Cancer Agents, Chemistry Select, 19, 2018, 5263-5268.
• D. L. Jardim, M. Schwaederle, D. S. Hong, R. Kurzrock, An appraisal of drug development timelines in the Era of precision oncology, Oncotarget, 7, 2016, 53037-53046.
• V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, Isonicotinic Acid Hydrazide Derivatives: Synthesis, Antimycobacterial, Antiviral, Antimicrobial Activity and QSAR Studies, Letters in Drug Design & Discovery, 8, 2011, 792-810.
• V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, E. De Clercq, C. Pannecouque, J. Balzarini, Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies, Medicinal Chemistry Research, 21, 2012, 1451-1470.
• D. Kumar, N.M. Kumar, S. Ghosh, K. Shah, Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents, Bioorganic & Medicinal Chemistry Letters, 22, 2012, 212-215.
• K.S. Kumar, S. Mohanty, G.P. Reddy, V. Siddaiah, J.D. Lilakar, G.L. Goud, Synthesis and Antimicrobial Activity of 3-{2-(1-Aryl-1H-1,2,3-triazol-4-yl)methoxy -5-fluorophenyl}isoxazoles, Russian Journal of General Chemistry, 89, 2019, 1221-1224.
• S. Kumar, B. Sharma, V. Mehra, V. Kumar, Recent accomplishments on the synthetic/biological facets of pharmacologically active 1H-1,2,3-triazoles, European Journal of Medicinal Chemistry, 212, 2021, 113069.
• S. Gallagher, M. Hashemzadeh, L.R. Peyton, Triazole antifungals: A review. Drugs Today, 51, 2015,705-718.
• H. H. Renate, M. G. Eric, L. Carmen, J. S. Peter, W. Baojie, G. F. Scott, G. Jiri, J. R. Philip, C. Kelly, Synthesis, antimalarial and antitubercular activity of acetylenic chalcones, Bioorganic & Medicinal Chemistry Letters, 20, 2010, 942-944.
• M. Cuendet, K. Hostettmann, O. Potterat, W. Dyatmiko, Iridoid Glucosides with Free Radical Scavenging Properties from Fagraea blumei, Helv Chim Acta, 80, 1997, 1144-1152. I.F. Benzie, J.J. Strain, The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay, Anal Biochem, 239, 1996, 70-76.
• F. Çelik, Y. Ünver, B. Barut, A. Özel, K. Sancak, Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry, Medicinal Chemistry, 14, 2018, 230-241.