| GONĚC, Tomáš, S POSPISILOVA, Tereza KAUEROVÁ, J KOS, J DOHANOSOVA, M ORAVEC, Peter KOLLÁR, A COFFEY, T LIPTAJ, Alois ČÍŽEK a J JAMPILEK. N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity. Molecules. BASEL: Mayer und Muller, 2016, roč. 21, č. 8, 18 s. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules21081068. |
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@article{1727125,
author = {Goněc, Tomáš and Pospisilova, S and Kauerová, Tereza and Kos, J and Dohanosova, J and Oravec, M and Kollár, Peter and Coffey, A and Liptaj, T and Čížek, Alois and Jampilek, J},
article_location = {BASEL},
article_number = {8},
doi = {http://dx.doi.org/10.3390/molecules21081068},
keywords = {hydroxynaphthalenecarboxamides; in vitro antimycobacterial activity; MTT assay; lipophilicity; structure-activity relationships},
language = {eng},
issn = {1420-3049},
journal = {Molecules},
title = {N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity},
volume = {21},
year = {2016}
}
TY - JOUR
ID - 1727125
AU - Goněc, Tomáš - Pospisilova, S - Kauerová, Tereza - Kos, J - Dohanosova, J - Oravec, M - Kollár, Peter - Coffey, A - Liptaj, T - Čížek, Alois - Jampilek, J
PY - 2016
TI - N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity
JF - Molecules
VL - 21
IS - 8
PB - Mayer und Muller
SN - 14203049
KW - hydroxynaphthalenecarboxamides
KW - in vitro antimycobacterial activity
KW - MTT assay
KW - lipophilicity
KW - structure-activity relationships
N2 - A series of nineteen N-(alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides and a series of their nineteen positional isomers N-(alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides were prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, M. kansasii and M. smegmatis. Screening of the cytotoxicity of the compounds was performed using human monocytic leukemia THP-1 cells. Some of the tested compounds showed antimycobacterial activity comparable with or higher than that of rifampicin. For example, 2-hydroxy-N-(4-propoxyphenyl)-naphthalene-1-carboxamide showed the highest activity (MIC = 12 mu M) against M. tuberculosis with insignificant cytotoxicity. N-[3-(But-2-yloxy) phenyl]-and N-[4-(but-2-yloxy) phenyl]-2-hydroxy-naphthalene-1-carboxamide demonstrated high activity against all tested mycobacterial strains and insignificant cytotoxicity. N-(Alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides demonstrated rather high effect against M. smegmatis and M. kansasii and strong antiproliferative effect against the human THP-1 cell line. Lipophilicity was found as the main physicochemical parameter influencing the activity. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) assay. Structure-activity relationships are discussed.
ER -
GONĚC, Tomáš, S POSPISILOVA, Tereza KAUEROVÁ, J KOS, J DOHANOSOVA, M ORAVEC, Peter KOLLÁR, A COFFEY, T LIPTAJ, Alois ČÍŽEK a J JAMPILEK. N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity. \textit{Molecules}. BASEL: Mayer und Muller, 2016, roč.~21, č.~8, 18 s. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules21081068.
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