Benzeneseleninic acid promoting the selenofunctionalization of 2-naphthol derivatives: Synthesis and antioxidant activity of 1-organoselanyl-naphthalen-2-ols

Current Chemical Biology Pub Date : 2022-12-20 DOI:10.2174/2212796817666221220100340

G. Perin, Daniela H. Mailahn, D. R. Araújo, P. Nobre, C. A. Fonseca, Filipe Penteado, E. Lenardão, C. Luchese, E. A. Wilhelm

{"title":"Benzeneseleninic acid promoting the selenofunctionalization of 2-naphthol derivatives: Synthesis and antioxidant activity of 1-organoselanyl-naphthalen-2-ols","authors":"G. Perin, Daniela H. Mailahn, D. R. Araújo, P. Nobre, C. A. Fonseca, Filipe Penteado, E. Lenardão, C. Luchese, E. A. Wilhelm","doi":"10.2174/2212796817666221220100340","DOIUrl":null,"url":null,"abstract":"\n\nWe report the synthesis and antioxidant evaluation of 1-organoselanyl-naphthalen-2-ols. The title compounds were selectively prepared through the selenofunctionalization of 2-naphthol derivatives using benzeneseleninic acids as a selenium source.\n\n\n\nWe 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.\n\n\n\nThe 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.\n\n\n\nA 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.\n\n\n\nThe 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.\n","PeriodicalId":10784,"journal":{"name":"Current Chemical Biology","volume":"56 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2022-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Chemical Biology","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/2212796817666221220100340","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}

引用次数: 1

Abstract

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

查看原文本刊更多论文

苯亚硒酸促进2-萘酚衍生物的硒化:1-有机塞拉烷-萘-2-醇的合成及其抗氧化活性

本文报道了1-有机塞拉基萘-2-醇的合成及其抗氧化性评价。以苯硒酸为硒源，通过2-萘酚衍生物的硒功能化选择性制备了标题化合物。以丙三醇为溶剂，用芳基亚硒酸对2-萘酚进行功能化，合成1-有机塞拉基-萘-2-醇，并进一步评价其药理活性。产物以甘油为溶剂，在70℃油浴中合成。进行活性物质(RS)测定、DPPH自由基清除活性测定和ABTS+自由基清除活性测定。对数据进行统计分析。在0.25 ~ 48 h的反应时间内，选择性地得到了15种1-有机塞拉烷-萘-2-醇，收率为58 ~ 95%。此外，所有合成的硒衍生物都具有抗氧化活性，可以清除DPPH和ABTS+自由基，降低活性物质(RS)水平。以苯乙烯酸衍生物与2-萘酚为原料，在温和反应条件下合成了1-芳基selanyl-萘-2-醇。所有合成的2-萘酚衍生物均具有抗氧化活性，表明其具有清除DPPH和ABTS+自由基的活性，并降低了RS水平。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Current Chemical Biology Medicine-Biochemistry (medical)

CiteScore

1.40

自引率

0.00%

发文量

期刊介绍： Current Chemical Biology aims to publish full-length and mini reviews on exciting new developments at the chemistry-biology interface, covering topics relating to Chemical Synthesis, Science at Chemistry-Biology Interface and Chemical Mechanisms of Biological Systems. Current Chemical Biology covers the following areas: Chemical Synthesis (Syntheses of biologically important macromolecules including proteins, polypeptides, oligonucleotides, oligosaccharides etc.; Asymmetric synthesis; Combinatorial synthesis; Diversity-oriented synthesis; Template-directed synthesis; Biomimetic synthesis; Solid phase biomolecular synthesis; Synthesis of small biomolecules: amino acids, peptides, lipids, carbohydrates and nucleosides; and Natural product synthesis).