| Identifikační kód |
RIV/61989592:15310/20:73604501 |
| Název v anglickém jazyce |
Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity |
| Druh |
J - Recenzovaný odborný článek (Jimp, Jsc a Jost) |
| Poddruh |
J/A - Článek v odborném periodiku je obsažen v databázi Web of Science společností Thomson Reuters s příznakem „Article“, „Review“ nebo „Letter“ (Jimp) |
| Jazyk |
eng - angličtina |
| Vědní obor |
30107 - Medicinal chemistry |
| Rok uplatnění |
2020 |
| Kód důvěrnosti údajů |
S - Úplné a pravdivé údaje o výsledku nepodléhající ochraně podle zvláštních právních předpisů. |
| Počet výskytů výsledku |
6 |
| Počet tvůrců celkem |
10 |
| Počet domácích tvůrců |
2 |
| Výčet všech uvedených jednotlivých tvůrců |
Josef Jampílek (státní příslušnost: CZ - Česká republika, domácí tvůrce: A, vedidk: 9033793, orcid: 0000-0003-2003-9052, scopusid: 6508328006)
Hana Michnová (státní příslušnost: CZ - Česká republika, domácí tvůrce: A, vedidk: 6489528, orcid: 0000-0002-2523-3092)
Július Gajdár (státní příslušnost: CZ - Česká republika, orcid: 0000-0003-1909-1400)
Konstantina Tsami (státní příslušnost: GR - Řecká republika) |
| Popis výsledku v anglickém jazyce |
Twenty-two novel antimycobacterial agents, 1-hydroxynaphthalene-2-carboxanilides, were studied by cyclic voltammetry on a glassy carbon electrode in a phosphate buffer pH 7.2 - dimethyl sulfoxide (DMSO) mixed medium (9:1; v/v). All compounds exhibited similar voltammetric behavior with one irreversible anodic signal in the range 100-300 mV corresponding to the oxidation of hydroxyl group on the naphthalene moiety. A shift of the oxidation potential was caused solely by electron donating or withdrawing effects of substituents and their position on the benzene moiety. Mechanism of oxidation in the studied medium was briefly outlined. Values of oxidation potentials exhibited very good linear correlation with calculated Hammett sigma substituent constants. For all active compounds, a relationship between oxidation potentials and MIC or IC50 values obtained from in vitro screening was investigated in detail. Primary in vitro screening of synthesized compounds was previously performed against three species of Mycobacterium pathogens. Additionally, their activity related to the inhibition of photosynthetic electron transport (PET) in spinach chloroplasts was tested in previous publications. In vitro screening against Mycobacterium tuberculosis was performed here for the first time with 1-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-2-carboxamide being the most effective (MIC = 11.7 mmol L-1). Furthermore, several other compounds showed higher antimycobacterial activity than the standard isoniazid. Relation of biological activities and oxidation potentials was successfully found in some cases; however, final correlations must also be considered with other physical and chemical factors contributing to the biological activity. Relation of structure, biological activity and electrochemical potential was also studied by cyclic voltammetry in cathodic area for three compounds containing reducible nitro moiety. |
| Klíčová slova oddělená středníkem |
Structure-activity relationship;Hammett correlation;Photosynthetic electron transport inhibition;Antimycobacterial activity;Hydroxynaphthalene-2-carboxanilides |
| Stránka www, na které se nachází výsledek |
https://www.sciencedirect.com/science/article/pii/S0013468619323576 |
| DOI výsledku |
https://doi.org/10.1016/j.electacta.2019.135485 |
| Odkaz na údaje z výzkumu |
- |