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

J 2021

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

GAJDAR, Július, Jiří KOS, Tomáš GONĚC, Marie BRÁZDOVÁ, Zuzana SOLDÁNOVÁ et. al.

Základní údaje

Originální název

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

Autoři

GAJDAR, Július (garant), Jiří KOS (203 Česká republika, domácí), Tomáš GONĚC (203 Česká republika, domácí), Marie BRÁZDOVÁ (203 Česká republika), Zuzana SOLDÁNOVÁ (203 Česká republika), Miroslav FOJTA (203 Česká republika), Josef JAMPÍLEK, Jiří BAREK (203 Česká republika) a Jan FISCHER (203 Česká republika)

Vydání

Journal of Electroanalytical Chemistry, Lausanne, Elsevier, 2021, 1572-6657

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Nizozemské království

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Odkaz na plný text výsledku nebo domovskou stánku výsledku

Impakt faktor

Impact factor: 4.598

Kód RIV

RIV/00216224:14110/21:00123094

Organizační jednotka

Lékařská fakulta

DOI

http://dx.doi.org/10.1016/j.jelechem.2021.115667

UT WoS

000702520400003

Klíčová slova anglicky

Hydroxynaphthalenecarboxanilides; Hammett correlation; Structure-activity relationships; Cyclic voltammetry

Štítky

14110512, podil, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 27. 1. 2022 13:18, Mgr. Tereza Miškechová

Anotace

V originále

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.

Citovat

GAJDAR, Július, Jiří KOS, Tomáš GONĚC, Marie BRÁZDOVÁ, Zuzana SOLDÁNOVÁ, Miroslav FOJTA, Josef JAMPÍLEK, Jiří BAREK a Jan FISCHER. 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. Lausanne: Elsevier, 2021, roč. 899, October 2021, s. 1-8. ISSN 1572-6657. Dostupné z: https://dx.doi.org/10.1016/j.jelechem.2021.115667.

@article{1806939,
   author = {Gajdar, Július and Kos, Jiří and Goněc, Tomáš and Brázdová, Marie and Soldánová, Zuzana and Fojta, Miroslav and Jampílek, Josef and Barek, Jiří and Fischer, Jan},
   article_location = {Lausanne},
   article_number = {October 2021},
   doi = {http://dx.doi.org/10.1016/j.jelechem.2021.115667},
   keywords = {Hydroxynaphthalenecarboxanilides; Hammett correlation; Structure-activity relationships; Cyclic voltammetry},
   language = {eng},
   issn = {1572-6657},
   journal = {Journal of Electroanalytical Chemistry},
   title = {Substituent effect of ring-substituted 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides in relation to their electrochemical and biological activity},
   url = {https://www.sciencedirect.com/science/article/pii/S1572665721006937?via%3Dihub},
   volume = {899},
   year = {2021}
}

TY  - JOUR
ID  - 1806939
AU  - Gajdar, Július - Kos, Jiří - Goněc, Tomáš - Brázdová, Marie - Soldánová, Zuzana - Fojta, Miroslav - Jampílek, Josef - Barek, Jiří - Fischer, Jan
PY  - 2021
TI  - Substituent effect of ring-substituted 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides in relation to their electrochemical and biological activity
JF  - Journal of Electroanalytical Chemistry
VL  - 899
IS  - October 2021
SP  - 1-8
EP  - 1-8
PB  - Elsevier
SN  - 15726657
KW  - Hydroxynaphthalenecarboxanilides
KW  - Hammett correlation
KW  - Structure-activity relationships
KW  - Cyclic voltammetry
UR  - https://www.sciencedirect.com/science/article/pii/S1572665721006937?via%3Dihub
N2  - 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.
ER  -

GAJDAR, Július, Jiří KOS, Tomáš GONĚC, Marie BRÁZDOVÁ, Zuzana SOLDÁNOVÁ, Miroslav FOJTA, Josef JAMPÍLEK, Jiří BAREK a Jan FISCHER. Substituent effect of ring-substituted 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides in relation to their electrochemical and biological activity. \textit{Journal of Electroanalytical Chemistry}. Lausanne: Elsevier, 2021, roč.~899, October 2021, s.~1-8. ISSN~1572-6657. Dostupné z: https://dx.doi.org/10.1016/j.jelechem.2021.115667.

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