Thiophenyl-chalcone derivatives: Synthesis, antioxidant activity, FMO energies and molecular parameters

Year 2023, Volume: 25 Issue: 1, 293 - 304, 16.01.2023

Fatih Sönmez Tuğçe Gür Zuhal Şahin

https://doi.org/10.25092/baunfbed.1119869

Abstract

In this study, a series of thiophenyl-chalcones derivatives was synthesized and their DPPH and ABTS activities were evaluated. All thiophenyl-chalcones exhibited high antioxidant activity. Among them, 4e ((E)-5-(3-(4-(chlorosulfonyl)-3-hydroxyphenyl)-3-oxoprop-1-en-1-yl)thiophene-2-sulfonyl chloride) have higher ABTS activity (IC50 = 13.12 μM) than quercetin (IC50 = 15.49 μM), well-known as antioxidant agent and used as a standard. The structure-activity relationship results revealed that most of synthesized sulfonyl chloride derivatives (4a-e) have higher antioxidant activity than the sulphonamide derivatives (5a-c) and also 4d and 4e including hydroxyl group, exhibited the strongest antioxidant activity as expected. Additionally, the frontier molecular orbitals (FMOs) energies and molecular parameters of the synthesized molecules were calculated to support experimental results. The quantum chemical calculation results indicated that the strongest antioxidant compounds, in this study, had the lowest LUMO energies and the highest electronegativity, electron affinity and electrophilicity index.

Keywords

Thiophene, chalcone, antioxidant activity

Tiyofenil-kalkon türevleri: Sentez, antioksidan aktivite, FMO enerjileri ve moleküler parametreler

Abstract

Bu çalışmada bir dizi tiyofenil-kalkon türevi sentezlendi ve bunların DPPH ve ABTS aktiviteleri incelendi. Tüm tiyofenil-kalkonlar yüksek antioksidan aktivite sergilemiştir. Bunlardan, 4e ((E)-5-(3-(4-(klorosülfonil)-3-hidroksifenil)-3-oksoprop-1-en-1-il)tiyofen-2-sülfonil klorür) antioksidan ajan olarak iyi bilinen ve standart olarak kullanılan quersetinden (IC50 = 13.12 μM) daha yüksek ABTS aktivitesine sahiptir. Yapı-aktivite ilişkisi sonuçları, sentezlenen sülfonil klorür türevlerinin (4a-e) sülfonamid türevlerinden (5a-c) daha yüksek antioksidan aktiviteye sahip olduğunu ve ayrıca hidroksil grubu içeren 4d ve 4e'nin beklendiği gibi en güçlü antioksidan aktiviteyi sergilediğini ortaya koymuştur. Ayrıca, deneysel sonuçları desteklemek için sentezlenen bileşiklerin sınır moleküler orbital (FMO) enerjileri ve moleküler parametreleri hesaplandı. Kuantum kimyasal hesaplama sonuçları, bu çalışmada en güçlü antioksidan bileşiklerin en düşük LUMO enerjilerine ve en yüksek elektronegatiflik, elektron afinitesi ve elektrofilik indeksine sahip olduğunu göstermiştir.

Keywords

tiyofen, kalkon, antioksidant aktivite

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