Synthesis and Biological Evaluation of
N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

J 2015

Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

GONĚC, Tomáš, I ZADRAZILOVA, E NEVIN, Tereza KAUEROVÁ, M PESKO et. al.

Základní údaje

Originální název

Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

Autoři

GONĚC, Tomáš, I ZADRAZILOVA, E NEVIN, Tereza KAUEROVÁ, M PESKO, J KOS, M ORAVEC, Peter KOLLÁR, A COFFEY, O Mahony J, Alois ČÍŽEK, K KRALOVA a J JAMPILEK

Vydání

Molecules, BASEL, Mayer und Muller, 2015, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Utajení

není předmětem státního či obchodního tajemství

Impakt faktor

Impact factor: 2.465

DOI

http://dx.doi.org/10.3390/molecules20069767

UT WoS

000357992700018

Klíčová slova anglicky

hydroxynaphthalene-2-carboxanilides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; structure-activity relationships

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 12. 3. 2021 00:00, PharmDr. Tomáš Goněc, Ph.D.

Anotace

V originále

A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 mu M against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 mu M and 24 mu M against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 mu M) was the most active PET inhibitor. The structure-activity relationships are discussed.

Citovat

GONĚC, Tomáš, I ZADRAZILOVA, E NEVIN, Tereza KAUEROVÁ, M PESKO, J KOS, M ORAVEC, Peter KOLLÁR, A COFFEY, O Mahony J, Alois ČÍŽEK, K KRALOVA a J JAMPILEK. Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides. Molecules. BASEL: Mayer und Muller, 2015, roč. 20, č. 6, s. 9767-9787. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules20069767.

@article{1727185,
   author = {Goněc, Tomáš and Zadrazilova, I and Nevin, E and Kauerová, Tereza and Pesko, M and Kos, J and Oravec, M and Kollár, Peter and Coffey, A and J, O Mahony and Čížek, Alois and Kralova, K and Jampilek, J},
   article_location = {BASEL},
   article_number = {6},
   doi = {http://dx.doi.org/10.3390/molecules20069767},
   keywords = {hydroxynaphthalene-2-carboxanilides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; structure-activity relationships},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides},
   volume = {20},
   year = {2015}
}

TY  - JOUR
ID  - 1727185
AU  - Goněc, Tomáš - Zadrazilova, I - Nevin, E - Kauerová, Tereza - Pesko, M - Kos, J - Oravec, M - Kollár, Peter - Coffey, A - J, O Mahony - Čížek, Alois - Kralova, K - Jampilek, J
PY  - 2015
TI  - Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
JF  - Molecules
VL  - 20
IS  - 6
SP  - 9767-9787
EP  - 9767-9787
PB  - Mayer und Muller
SN  - 14203049
KW  - hydroxynaphthalene-2-carboxanilides
KW  - in vitro antibacterial activity
KW  - in vitro antimycobacterial activity
KW  - in vitro cytotoxicity
KW  - photosynthetic electron transport inhibition
KW  - structure-activity relationships
N2  - A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 mu M against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 mu M and 24 mu M against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 mu M) was the most active PET inhibitor. The structure-activity relationships are discussed.
ER  -

GONĚC, Tomáš, I ZADRAZILOVA, E NEVIN, Tereza KAUEROVÁ, M PESKO, J KOS, M ORAVEC, Peter KOLLÁR, A COFFEY, O Mahony J, Alois ČÍŽEK, K KRALOVA a J JAMPILEK. Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides. \textit{Molecules}. BASEL: Mayer und Muller, 2015, roč.~20, č.~6, s.~9767-9787. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules20069767.

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