Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones

Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3<i>H</i>)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TE...

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Autores principales:	Janez Mravljak, Lara Slavec, Martina Hrast, Matej Sova
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	quinazolinone synthesis antioxidant DPPH ABTS CUPRAC Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/e73e428c490f4cc191f015f12b1a5666
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spelling	oai:doaj.org-article:e73e428c490f4cc191f015f12b1a56662021-11-11T18:33:53ZSynthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones10.3390/molecules262165851420-3049https://doaj.org/article/e73e428c490f4cc191f015f12b1a56662021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6585https://doaj.org/toc/1420-3049Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3<i>H</i>)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEAC<sub>CUPRAC</sub>, to obtain key information about the structure–antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEAC<sub>CUPRAC</sub> assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3<i>H</i>)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds <b>25a</b> and <b>25b</b>), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2,3-dihydroxyphenyl)quinazolin-4(3<i>H</i>)-one <b>21e</b> as a potent antioxidant with promising metal-chelating properties.Janez MravljakLara SlavecMartina HrastMatej SovaMDPI AGarticlequinazolinonesynthesisantioxidantDPPHABTSCUPRACOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6585, p 6585 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	quinazolinone synthesis antioxidant DPPH ABTS CUPRAC Organic chemistry QD241-441
spellingShingle	quinazolinone synthesis antioxidant DPPH ABTS CUPRAC Organic chemistry QD241-441 Janez Mravljak Lara Slavec Martina Hrast Matej Sova Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones
description	Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3<i>H</i>)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEAC<sub>CUPRAC</sub>, to obtain key information about the structure–antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEAC<sub>CUPRAC</sub> assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3<i>H</i>)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds <b>25a</b> and <b>25b</b>), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2,3-dihydroxyphenyl)quinazolin-4(3<i>H</i>)-one <b>21e</b> as a potent antioxidant with promising metal-chelating properties.
format	article
author	Janez Mravljak Lara Slavec Martina Hrast Matej Sova
author_facet	Janez Mravljak Lara Slavec Martina Hrast Matej Sova
author_sort	Janez Mravljak
title	Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones
title_short	Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones
title_full	Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones
title_fullStr	Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones
title_full_unstemmed	Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones
title_sort	synthesis and evaluation of antioxidant properties of 2-substituted quinazolin-4(<i>3h</i>)-ones
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/e73e428c490f4cc191f015f12b1a5666
work_keys_str_mv	AT janezmravljak synthesisandevaluationofantioxidantpropertiesof2substitutedquinazolin4i3hiones AT laraslavec synthesisandevaluationofantioxidantpropertiesof2substitutedquinazolin4i3hiones AT martinahrast synthesisandevaluationofantioxidantpropertiesof2substitutedquinazolin4i3hiones AT matejsova synthesisandevaluationofantioxidantpropertiesof2substitutedquinazolin4i3hiones
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Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(<i>3H</i>)-ones

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