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Current Chemical Biology

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ISSN (Print): 2212-7968
ISSN (Online): 1872-3136

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Research Article

Benzeneseleninic Acid Promoting the Selenofunctionalization of 2- Naphthol Derivatives: Synthesis and Antioxidant Activity of 1- Organoselanyl-naphthalen-2-ols

Author(s): Daniela H. Mailahn, Daniela R. Araujo, Patrick C. Nobre, Caren A. R. Fonseca, Filipe Penteado, Eder J. Lenardão*, Cristiane Luchese, Ethel A. Wilhelm and Gelson Perin*

Volume 17, Issue 1, 2023

Published on: 29 December, 2022

Page: [56 - 66] Pages: 11

DOI: 10.2174/2212796817666221220100340

Price: $65

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Abstract

Background: We report the synthesis and antioxidant evaluation of 1-organoselanylnaphthalen- 2-ols. The title compounds were selectively prepared through the selenofunctionalization of 2-naphthol derivatives using benzeneseleninic acids as a selenium source.

Objective: We aimed at synthesizing 1-organoselanyl-naphthalen-2-ol by functionalizing 2-naphthol with arylseleninic acids using glycerol as the solvent and further evaluating the pharmacological activity.

Methods: The products were synthesized at 70°C using glycerol as a solvent in an oil bath. Reactive species (RS) tests, DPPH radical scavenging activity assay, and ABTS+ radical scavenging activity assay were performed. A statistical analysis of the data was performed.

Results and Discussion: A total of fifteen 1-organoselanyl-naphthalen-2-ols were selectively obtained in yields of 58-95% in 0.25-48 h of reaction. Additionally, all the synthesized seleno-derivatives exhibited antioxidant activity, as revealed by their ability to scavenge DPPH and ABTS+ radicals and reduce the reactive species (RS) levels.

Conclusion: The synthesis of 1-arylselanyl-naphthalen-2-ols was developed under mild reaction conditions using benzeneseleninic acid derivatives in reactions with 2-naphthol. All synthesized 2- naphthol derivatives exhibited antioxidant activity, as revealed by their DPPH and ABTS+ radical scavenging activity and reduced RS levels.

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