Substituent effect of ring-substituted 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides in relation to their electrochemical and biological activity

0546621 - BFÚ 2022 RIV CH eng J - Journal Article
Gajdar, J. - Kos, J. - Gonec, T. - Brázdová, Marie - Soldanová, Zuzana - Fojta, Miroslav - Jampílek, J. - Barek, J. - Fischer, J.
Substituent effect of ring-substituted 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides in relation to their electrochemical and biological activity.
Journal of Electroanalytical Chemistry. Roč. 899, OCT 15 2021 (2021), č. článku 115667. ISSN 1572-6657. E-ISSN 1873-2569
Institutional support: RVO:68081707
Keywords : herbicidal activity * antioxidant activity * antimycobacterial * antibacterial * agents
OECD category: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Impact factor: 4.598, year: 2021
Method of publishing: Limited access
https://www.sciencedirect.com/science/article/pii/S1572665721006937?via%3Dihub

Two groups of novel anti-infective agents, 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides, were studied by voltammetric techniques at the glassy carbon electrode in aqueous media. Oxidation of hydroxyl group was observed for all forty-four studied compounds, all of them differentiated by a position and a substituent on the benzene moiety. A shift of the oxidation potential was observed for all cases based on electron-donating or electron-withdrawing properties of substituents. These shifts were successfully correlated with Hammett sigma substituent constants for meta- and para- substituted compounds. The observed differences in electrochemical behaviour (a shift of the oxidation potential of the unsubstituted compound, and the changes in the value of the reaction constant rho) between the two studied groups were highlighted and discussed. In addition, an attempt was made to correlate the electrochemical behaviour with the previously obtained in vitro anti-infective (antibacterial, antimycobacterial, antiprotozoal) activities and herbicidal activity. Due to the moderate activity only limited conclusions could be made. However, good relationships were observed between the oxidation potential and antitrypanosomal activities.
Permanent Link: http://hdl.handle.net/11104/0323067