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

Year 2017, Issue: 1, 36 - 42, 31.12.2017

Ergün Gültekin , Uğur Kardil Yeşim Topaloğlu Miraç Ocak , Nuri Yıldırım , Semra Alkan Murat Küçük , Hakan Bektaş , Olcay Bekircan

Abstract

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

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

Abstract

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.

Keywords

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

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