20.500.12556/RUL-136429 Synthesis and evaluation of antioxidant properties of 2-substituted quinazolin-4(3H)-ones 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 TEAC$_{CUPRAC}$, 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$_{CUPRAC}$ 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. quinazolinone synthesis antioxidant DPPH ABTS CUPRAC metal-chelating properties antioksidanti sinteze lastnosti keliranja kovin kinazolinoni farmacevtska kemija true false true Angleški jezik Slovenski jezik Članek v reviji 2022-05-04 08:08:32 2022-05-04 08:08:40 2022-09-15 04:13:52 0000-00-00 00:00:00 2021 0 0 16 str. iss. 21, art. 6585 Vol. 26 2021 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 543:615.4:54 1420-3049 10.3390/molecules26216585 83008003 molecules-26-06585-v2.pdf molecules-26-06585-v2.pdf 1 558775D9B63A8540ED6F3231D771AB8E c6ebb4e9efa633447b77f9a145bd3bd26ef97605562fc7a4d3252108e7bb4b02 d9542bac-cb70-11ec-8aca-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=156078 https://www.mdpi.com/1420-3049/26/21/6585 1 8d87529a-cb70-11ec-8aca-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=156077 Fakulteta za farmacijo 0 0 0