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28. Synthesis and in vitro antioxidant activity study of some new piperazinyl flavone compounds.

Author

Berczyński, Paweł, Kładna, Aleksandra, Kruk, Irena, Sarı, Elmas, Murat, Hatice Nehir, Bozdağ Dündar, Oya, and Aboul‐Enein, Hassan Y.

Abstract

Flavones exhibit a variety of beneficial effects and are well known for their medicinal importance in several diseases, including cardiovascular, neurodegenerative and cancer. The inclusion of the piperazine ring to the flavone backbone is an important strategy in drug discovery but only a few studies have synthesized piperazinyl flavone compounds to test their biological activity. While there is a major focus on the antioxidant properties of drugs in therapy of several diseases of inflammatory origin, we synthesized a series of the novel piperazinyl flavone analogues bearing the phenyl ring with different substituents. The analogues were evaluated for in vitro antioxidant activity against superoxide anion radical, hydroxyl radical, 2,2-diphenyl-1-picrylhydrazyl radical, and hydrogen peroxide scavenging properties. The total antioxidant status based on the absorbance of the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS+•) and total antioxidant capacity using the Fe(III)-ferrozine complex were also monitored. The results of the above studies showed that the compounds synthesized were found possessed moderate radical scavenging potential, and that their interaction with reactive oxygen species is complex and depends on their structural conformation and the type of substituent R in the piperazine ring being attached. Best antiradical activity were found for the compounds with methoxy groups on the phenyl ring of substituent R, whereas the presence of methoxy or trifluoromethyl groups in substituent R resulted in higher ABTS+• and ion Fe(III) reduction. These compounds are promising molecules to be used for their antioxidant properties and may be regarded, after improvement of the antioxidant potential, to control diseases of free radical etiology. [ABSTRACT FROM AUTHOR]

Published
2017
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49. Studies on the antioxidant activity of some chromonylrhodanine derivatives.

Author

Kruk, Irena, Piechowska, Teresa, Berczyński, Paweł, Kładna, Aleksandra, Bozdağ‐Dündar, Oya, Ceylan‐Unlusoy, Meltem, and Aboul‐Enein, Hassan Y.

Abstract

Fifteen chromonylrhodamine derivatives (CRs) were synthesized and the antioxidant activity levels were evaluated for the first time. The antioxidant activity potencies of these chromone derivatives were evaluated towards superoxide anion radicals, hydroxyl radicals and 2,2-diphenyl-1-picrylhydrazyl radicals. Also, the total antioxidant capacity of the tested compounds was measured using the ferric-ferrozine assay. The antioxidant activities were investigated using a chemiluminescence (CL) assay, spectrophotometry measurements, direct electron paramagnetic resonance (EPR) and the EPR spin-trapping technique. The 5,5-dimethyl- 1-pyrroline-1-oxide (DMPO) was applied as spin trap. Eleven of the 15 chromone compounds exhibited a decrease in the CL accompanying the superoxide anion radical produced in anhydrous dimethylsulfoxide (DMSO), ranging from 71-94% at concentration of 1 mmol /L; four of these compounds enhanced light emission in the range 231-672%. Similarly, these compounds caused 28-58% inhibition in the intensity of the DMPO-OOH radical EPR signal and the DMPO-OH radical (from 12-48%). Furthermore, three of these compounds showed very good antioxidant response towards the DPPH radical (EC50: 0.51-0.56 µmol/L) and the high reduction potentials. These findings demonstrate that the chromone compounds tested may be considered as effective free radicals scavengers, a finding that is of great pharmacological importance. Copyright © 2014 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

Published
2015
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