Electrochemistry of ring-substituted
1-hydroxynaphthalene-2-carboxanilides: Relation to structure
and biological activity

J 2020

Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity

GAJDAR, J., K. TSAMI, H. MICHNOVA, Tomáš GONĚC, M. BRAZDOVA et. al.

Základní údaje

Originální název

Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity

Autoři

GAJDAR, J., K. TSAMI, H. MICHNOVA, Tomáš GONĚC (203 Česká republika, domácí), M. BRAZDOVA, Z. SOLDANOVA, M. FOJTA, J. JAMPILEK, J. BAREK a J. FISCHER (garant)

Vydání

Electrochimica Acta, OXFORD, Elsevier, 2020, 0013-4686

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 6.901

Kód RIV

RIV/00216224:14160/20:00118087

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1016/j.electacta.2019.135485

UT WoS

000506201800049

Klíčová slova anglicky

Hydroxynaphthalene-2-carboxanilides; Antimycobacterial activity; Photosynthetic electron transport inhibition; Hammett correlation; Structure-activity relationship

Štítky

afiliace VFU, rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 24. 2. 2021 13:08, Mgr. Hana Hurtová

Anotace

V originále

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. (C) 2019 Elsevier Ltd. All rights reserved.

Citovat

GAJDAR, J., K. TSAMI, H. MICHNOVA, Tomáš GONĚC, M. BRAZDOVA, Z. SOLDANOVA, M. FOJTA, J. JAMPILEK, J. BAREK a J. FISCHER. Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity. Electrochimica Acta. OXFORD: Elsevier, 2020, roč. 332, FEB 1 2020, s. 1-10. ISSN 0013-4686. Dostupné z: https://dx.doi.org/10.1016/j.electacta.2019.135485.

@article{1736828,
   author = {Gajdar, J. and Tsami, K. and Michnova, H. and Goněc, Tomáš and Brazdova, M. and Soldanova, Z. and Fojta, M. and Jampilek, J. and Barek, J. and Fischer, J.},
   article_location = {OXFORD},
   article_number = {FEB 1 2020},
   doi = {http://dx.doi.org/10.1016/j.electacta.2019.135485},
   keywords = {Hydroxynaphthalene-2-carboxanilides; Antimycobacterial activity; Photosynthetic electron transport inhibition; Hammett correlation; Structure-activity relationship},
   language = {eng},
   issn = {0013-4686},
   journal = {Electrochimica Acta},
   title = {Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity},
   url = {https://www.sciencedirect.com/science/article/pii/S0013468619323576?via%3Dihub},
   volume = {332},
   year = {2020}
}

TY  - JOUR
ID  - 1736828
AU  - Gajdar, J. - Tsami, K. - Michnova, H. - Goněc, Tomáš - Brazdova, M. - Soldanova, Z. - Fojta, M. - Jampilek, J. - Barek, J. - Fischer, J.
PY  - 2020
TI  - Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity
JF  - Electrochimica Acta
VL  - 332
IS  - FEB 1 2020
SP  - 1-10
EP  - 1-10
PB  - Elsevier
SN  - 00134686
KW  - Hydroxynaphthalene-2-carboxanilides
KW  - Antimycobacterial activity
KW  - Photosynthetic electron transport inhibition
KW  - Hammett correlation
KW  - Structure-activity relationship
UR  - https://www.sciencedirect.com/science/article/pii/S0013468619323576?via%3Dihub
L2  - https://www.sciencedirect.com/science/article/pii/S0013468619323576?via%3Dihub
N2  - 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. (C) 2019 Elsevier Ltd. All rights reserved.
ER  -

GAJDAR, J., K. TSAMI, H. MICHNOVA, Tomáš GONĚC, M. BRAZDOVA, Z. SOLDANOVA, M. FOJTA, J. JAMPILEK, J. BAREK a J. FISCHER. Electrochemistry of ring-substituted 1-hydroxynaphthalene-2-carboxanilides: Relation to structure and biological activity. \textit{Electrochimica Acta}. OXFORD: Elsevier, 2020, roč.~332, FEB 1 2020, s.~1-10. ISSN~0013-4686. Dostupné z: https://dx.doi.org/10.1016/j.electacta.2019.135485.

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