Ergün GÜLTEKİN, Uğur KARDİL, Yeşim TOPALOĞLU, Miraç OCAK, Nuri YILDIRIM, Semra ALKAN, Murat KÜÇÜK, Hakan BEKTAŞ, Olcay BEKİRCAN

Bazı yeni 1,2,4-triazol türevlerinin sentezi, floresans özellikleri ve biyolojik aktivitelerinin incelenmesi

Bu çalışmada, iminoester hidroklorürler ve benzhidrazidden başlanarak 1,2,4-triazol halkası içeren yeni heterosiklik bileşikler sentezlendi. Triazol bileşiklerinin floresans özellikleri metanol ve DMSO gibi organik çözücülerde belirlendi. Triazol bileşikleri arasında diimin bileşikleri metanolde yüksek floresans şiddeti gösterdi. İndirgenmiş bileşikler (8) dimin bileşiklerine (6) göre metanolde düşük floresans özelliğine sahiptir. Yeni sentezlenen bileşiklerin antioksidan ve karbonik anhidraz inhibitör (CAI) aktiviteleri incelendi. Bileşiklerde düşük CAI aktivitesi gözlendi. Bis Schiff bazları (6), 200 ve 330 μM'ın altındaki IC50 değerleriyle daha iyi aktiviteye sahipti. Bileşikler DPPH ve FRAP testlerinin her ikisinde de orta ve yüksek seviyede antioksidan aktivite gösterdi. DPPH radikal temizleme testinde bileşiklerin bazılarının SC50 değerleri standart antioksidanlarınkine yakın 0,01 mg/mL seviyesinde olduğu görüldü. Benzer şekilde 8197 mM TEAC değeriyle yüksek FRAP aktivitesi tespit edildi. Yeni bileşiklerin yapısal farklılıkları antioksidan aktivitelerinde etkili oldu. Benzoilhidrazonlar (2), oksadiazoller (3) ve amino-triazoller (4), 5-8 billeşiklerine kıyasla yüksek aktivite gösterdiler.

Anahtar Kelimeler:

1.2.4-triazol, Schiff bazı, antioksidan, floresans, karbonik anhidraz inhibitör aktivitesi

Synthesis of some new 1,2,4-triazole derivatives, investigation of their fluorescence properties and biological activities

In this work, new heterocyclic compounds containing 1,2,4-triazole ring were synthesized starting from iminoester hydrochlorides and benzhydrazide. The fluorescence properties of the novel triazole compounds synthesized were determined in organic solvents such as methanol and DMSO. The diimine derivatives among the new triazoles show high fluorescence intensities in methanol. Reduced diimines (8) have lower fluorescence properties in methanol than diimine compounds (6). The compounds were also tested for their antioxidant and carbonic anhydrase inhibitory (CAI) activities. Low CAI activity was observed. Bis Schiff bases (6) showed better activity with lower IC50 values of 200 and 330 μM. The compounds showed moderate to high antioxidant activity in both DPPH and FRAP antioxidant tests. The SC50 values in DPPH test were as low as 0.01 mg/mL, close to that of standard antioxidants. Similarly, a high TEAC value as 8197 mM was observed showing considerably high FRAP activity. Structural differences were effective on the antioxidant activities of the new compounds. Benzoylhydrazones (2), oxadiazoles (3) and amino-triazoles (4) showed higher activity in both antioxidant tests as compared to compounds 5-8.

Keywords:

1.2.4-triazoles, Schiff bases, antioxidant, fluorescence, carbonic anhydrase inhibitory activity,

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