Synthesis and biological activity investigation of new 3,5-disubstituted-2-pyrazoline derivatives

Abstract

In this study 3 new pyrazolines, one of the electron-rich nitrogen containing heterocyclics, derivative compounds were synthesized starting from chalcones. Due to the biological and pharmacological properties of pyrazolines, DPPH radical scavenging and phosphomolybdenum reducing power (PRAP) activities and tyrosinase and α-glycosidase enzyme inhibition activities of these compounds were investigated . Based on the obtained results, it was determined that compounds 4 (IC50 = 16.68 ± 0.19 μM) and 6 (IC50 = 22.60 ± 0.83 μM) had better tyrosinase inhibitory activities than standard kojic acid (IC50 = 35.41 ± 0.19 μM). Although the α-glucosidase enzyme inhibition activities of the compounds were not very high, compound 4 (IC50 = 134.24 ± 2.51 μM) showed the highest activity. When the antioxidant activity values of the compounds were examined, compound 5 showed the highest DPPH radical scavenging (67.59 ± 0.44%) and phosphomolybdenum reducing power (PRAP, Abs = 0.815 ± 0.009) activities. As a result, the binding position of the -NH2 group, which differed in the compound structures, also caused a significant difference in the biological properties of the compounds..

Keywords

• Pyrazoline,tyrosinase and α-glycosidase inhibition,DPPH and PRAP antioxidant activity

Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi

Abstract

Bu çalışmada elektronca zengin azot atomu içeren 5 üyeli heterosikliklerden biri olan pirazolin türevi 3 adet yeni bileşik kalkonlardan başlanarak sentezlendi. Pirazolinlerin sahip oldukları biyolojik ve farmakolojik özelliği sebebiyle bu bileşiklerin DPPH radikal süpürme ve fosfomolibdenyum indirgeyici güç (PRAP) aktiviteleri ile tirozinaz ve α-glikozidaz enzim inhibisyon aktiviteleri araştırıldı. Elde edilen veriler doğrultusunda 4 (IC50=16.68 ± 0.19 μM) ve 6 (IC50=22.60 ± 0.83 μM) nolu bileşiklerin standart kojik asitten (IC50=35.41 ± 0.19 μM) daha iyi tirozinaz inhibisyon aktiviteye sahip oldukları belirlendi. Bileşiklerin α-glukozidaz enzim inhibisyon aktiviteleri çok yüksek olmamakla birlikte 4 (IC50=134.24 ± 2.51 μM) nolu bileşik en yüksek aktiviteyi gösterdi. Bileşiklerin antioksidan aktivite değerlerine bakıldığında ise 5 nolu bileşik en yüksek DPPH radikal süpürme (%67.59 ± 0.44) ve fosfomolibdenyum indirgeyici güç (PRAP, Abs= 0.815 ± 0.009) aktivitesini sergiledi. Sonuç olarak bileşik yapılarında farklılık gösteren -NH2 grubunun bağlanma pozisyonu, bileşiklerin biyolojik özelliklerinde belirgin bir farklılığa sebep olmuştur.

Keywords

• Pirazolin,tirozinaz ve α-glikozidaz inhibisyonu,DPPH ve PRAP antioksidan aktivite

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