SYNTHESIS AND ANTIRADICAL ACTIVITY OF ALKYL DERIVATIVES OF 5-(5-METHYL-1H-PYRAZOL-3-YL)-4-PHENYL-4H1,2,4-TRIAZOLE-3-THIOL

Öz

Objective: The aim of the work was to develop effective methods for the synthesis of biologically active heterocyclic systems containing 1,2,4-triazole and pyrazole.

Material and Method: Chemical structures of synthesized compounds were characterized with elemental analysis, IR, 1H-NMR, LC-MS techniques. The antiradical activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay.

Result and Discussion: Developed optimal methods of obtaining of alkylderivatives of 5-(5-methyl-1H-pyrazol-3-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol. A number of synthesized compounds showed moderate antiradical activity.

Anahtar Kelimeler

• antiradical activity
• pyrazole
• synthesis
• 1.2.4-triazoles

5-(5-METİL-1H-PİRAZOL-3-İL)-4-FENİL-4H-1,2,4-TRİAZOL-3-TİYOL ALKİL TÜREVLERİNİN SENTEZ VE ANTİRADİKAL AKTİVİTELERİ

Öz

Amaç: Çalışmanın amacı biyolojik olarak aktif 1,2,4-triazol ve pirazol içeren heterosiklik sistemlerin sentezi için etkili yöntemler geliştirmektir.

Gereç ve Yöntem: Sentezlenen bileşiklerin kimyasal yapıları elemantal analiz, IR, 1H-NMR, LC-MS teknikleri ile karakterize edildi. Antiradikal aktivite 2,2-difenil-1-pikrilhidrazil (DPPH) radikal süpürücü aktivite deneyi kullanılarak değerlendirildi.

Sonuç ve Tartışma: 5-(5-metil-1H-pirazol-3-il)-4-fenil-4H-1,2,4-triazol-3-tiyol alkil türevlerinin elde edilmesi için optimum yöntemler geliştirildi. Bir dizi sentezlenmiş bileşik, orta derecede antiradikal aktivite göstermiştir.

Anahtar Kelimeler

• antiradikal aktivite
• pirazol
• sentez
• 1.2.4-triazol

Kaynakça

1. 1. Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y., Al-aizari, F., Ansar, M. (2018). Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review. Molecules, 23, 134.
2. 2. Al-Ghamdi, H. M. (2019). Synthesis and antimicrobial activity of novel pyrazole derivatives. Oriental journal of chemistry, 35 (1), 391-398.
3. 3. Vijesh, A. M., Isloor, A. M., Shetty, P., Sundershan, S., Fun, H. K. (2013). New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents. European Journal of Medicinal Chemistry, 62, 410-415.
4. 4. Kharb, R., Sharma P. C., Bhandari, A., Yar, M. S. (2012). Synthesis, spectral characterization and anthelmintic evaluation of some novel imidazole bearing triazole derivatives / Der Pharmacia Lettre, 4 (2), 652-657.
5. 5. Hassan, G. S, Abdel Rahman D. E., Abdelmajeed E. A., Refaey R. H., Alaraby, S. M., Nissan, Y. M. (2019). New pyrazole derivatives: Synthesis, anti-inflammatory activity, cycloxygenase inhibition assay and evaluation of mPGES. Eurohean Journal of Medicinal Chemistry, 171, 332-342.
6. 6. Li, Y.-S., Tian, H., Zhao, D.-S., Hu, D.-K., Liu, X.-Y., Jin, H.-W., Cui, Z.-N. (2016). Synthesis and bioactivity of pyrazole and triazole derivatives as potential PDE4 inhibitors. Bioorganic & Medicinal Chemistry Letters, 26 (15), 3632-3635.
7. 7. Ashok, D., Kavitha, R., Gundu, S., Rao, V. H. (2017). Microwave-assisted synthesis of new pyrazole derivatives bearing 1,2,3-triazole scaffold as potential antimicrobial agents. Journal of the Serbian Chemical Society, 82 (4), 357-366.
8. 8. Hotsulia, A. S., Fedotov, S. O. (2019). Synthesis, structure and properties of N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides / Current issues in pharmacy and medicine: science and practice, 12 (1), 4-9.

9. 9. Kazunin, M. S., Voskoboynik, O. Yu., Nosulenko, I. S., Berest, G. G., Sergeieva, T., Okovytyy, S., Karpenko, O. V., Priimenko, B. O., Kovalenko, S. I. (2018). Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives / Journal of Heterocyclic Chemistry, 55 (4), 1033-1041.