Synthesis and evaluation of antioxidant properties of 2-substituted quinazolin-4(3H)-ones

Janez Mravljak (Author), Lara Slavec (Author), Martina Hrast (Author), Matej Sova (Author)

Abstract

Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, 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 TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-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 25a and 25b), 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(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.

Keywords

antioksidanti;sinteze;lastnosti keliranja kovin;kinazolinoni;quinazolinone;synthesis;antioxidant;DPPH;ABTS;CUPRAC;metal-chelating properties;

Data

Language:	English
Year of publishing:	2021
Typology:	1.01 - Original Scientific Article
Organization:	UL FFA - Faculty of Pharmacy
UDC:	543:615.4:54
COBISS:	83008003
ISSN:	1420-3049
Views:	117
Downloads:	54
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	Slovenian
Secondary keywords:	Farmacevtska kemija;
Type (COBISS):	Article
Pages:	str. 1-16
Volume:	ǂVol. ǂ26
Issue:	ǂiss. ǂ21
Chronology:	2021
DOI:	10.3390/molecules26216585
ID:	15209458