Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/10851
Title: Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies
Authors: Jakovljević, Katarina
Joksović, Milan
Botta, Bruno
Jovanović, Ljiljana
Avdović, Edina
Marković, Zoran
Mihailovic, Vladimir
Andric, Miroslav
Trifunović, Snežana
Marković, Violeta
Issue Date: 2019
Abstract: © 2019 Académie des sciences A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechanism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation.
URI: https://scidar.kg.ac.rs/handle/123456789/10851
Type: article
DOI: 10.1016/j.crci.2019.06.001
ISSN: 1631-0748
SCOPUS: 2-s2.0-85068213922
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac

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