A Study on Synthesis and Antioxidant Activity Comparison of Novel Stilbenebenzamide Compounds

Author(s): Aleksandra Kładna, Paweł Berczyński, Oya B. Dündar, Irena Kruk, Beyza Torun, Hassan Y. Aboul-Enein*

Journal Name: Medicinal Chemistry

Volume 17 , Issue 5 , 2021


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Abstract:

Background: Stilbene phytalexis (1,2-diphenyloethylen) and benzamide are beneficial for human health. To increase the stilbene ring activity, a new series of its derivatives containing benzamide structure was synthesized and evaluated for their in vitro antioxidant power.

Methods: 1H nuclear magnetic resonance, mass spectroscopy, and chromatographic analyses were used to confirm the successful synthesis. The antioxidant properties were determined by the elimination of O2˙-, HO˙ , DPPH˙ , ABTS+˙ radicals, total antioxidant status (TAS) and the ferric reducing antioxidant activities (TAC) measurements.

Results: Stilbenebenzamide compounds showed a wide spectrum of antioxidant ability; however, their total antioxidant power was weaker than those of butylated hydroxytoluene (BHT), ascorbic acid, and resveratrol. The highest antiradical activity towards O2˙ and HO˙ was shown by the compounds with structures containing amine group (SBEBA, SBA) (O2˙: 37.7 – 38.0% and 40.8 – 43.5%, HO˙ : 29.8%, 28.7% inhibition, respectively) at1.25 mM concentration. The antiradical power of SBEBA (0.29) in DPPH˙ assay was lower than those of resveratrol (1.83), ascorbic acid (3.63) and BHT (4.09). The TAS values of the synthesized compounds ranged from 152.9±5.3 to 240.2±6.7μM trolox equivalent/gram (TE/g) and were much lower than those of BHT (1304±43.0), reservatrol (1360±29.0) and ascorbic acid (2782±39.7) μM TE/g. Similarly, the TAC values ranging from 29.7±0.9 to 41.5±1.6 μM TE were weaker than that of resveratrol (239.2 ±6.7 μM TE/g).

Conclusion: The results suggest that the presence of the hydroxyl group in the stilbene ring should be considered in the further design of stilbenebenzamide compounds to enhance their antioxidant activity.

Keywords: Stilbenebenzamide compounds, radical scavenging activity, TAS, TAC, mass spectroscopy, chromatographic analyses.

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Article Details

VOLUME: 17
ISSUE: 5
Year: 2021
Published on: 24 May, 2021
Page: [533 - 544]
Pages: 12
DOI: 10.2174/1573406415666191114123004
Price: $65

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