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.

Basic information

Original name

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

Authors

GAJDAR, Július (guarantor), Jiří KOS (203 Czech Republic, belonging to the institution), Tomáš GONĚC (203 Czech Republic, belonging to the institution), Marie BRÁZDOVÁ (203 Czech Republic), Zuzana SOLDÁNOVÁ (203 Czech Republic), Miroslav FOJTA (203 Czech Republic), Josef JAMPÍLEK, Jiří BAREK (203 Czech Republic) and Jan FISCHER (203 Czech Republic)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Netherlands

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Odkaz na plný text výsledku nebo domovskou stánku výsledku

Impact factor

Impact factor: 4.598

RIV identification code

RIV/00216224:14110/21:00123094

Organization unit

Faculty of Medicine

DOI

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

UT WoS

000702520400003

Keywords in English

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

Abstract

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 and 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, vol. 899, October 2021, p. 1-8. ISSN 1572-6657. Available from: 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 and 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, vol.~899, October 2021, p.~1-8. ISSN~1572-6657. Available from: https://dx.doi.org/10.1016/j.jelechem.2021.115667.

Detailed Information on Publication Record