Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16370%2F15%3A43873818" target="_blank" >RIV/62157124:16370/15:43873818 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.bmc.2015.03.018" target="_blank" >http://dx.doi.org/10.1016/j.bmc.2015.03.018</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bmc.2015.03.018" target="_blank" >10.1016/j.bmc.2015.03.018</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides

Popis výsledku v původním jazyce

In this study, a series of twenty-two ring-substituted 6-hydroxynaphthalene-2-carboxanilides was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, Mycobacterium avium complex and M. avium subsp. paratuberculosis. Derivatives substituted by trifluoromethyl, bromo, methyl and methoxy moieties in C-(3)' and C-(4)' positions of the anilide ring showed 2-fold higher activity against M. tuberculosis than isoniazid and 4.5-fold higher activity against M. avium subsp. paratuberculosis than rifampicin. 6-Hydroxy-N-(2-methylphenyl) naphthalene-2-carboxamide had MIC = 29 mu M against M. avium complex. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT assay. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using the THP-1 cells, and no significant lethal effect was observed. The structure-activity relationships are discussed.

Název v anglickém jazyce

Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides

Popis výsledku anglicky

In this study, a series of twenty-two ring-substituted 6-hydroxynaphthalene-2-carboxanilides was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, Mycobacterium avium complex and M. avium subsp. paratuberculosis. Derivatives substituted by trifluoromethyl, bromo, methyl and methoxy moieties in C-(3)' and C-(4)' positions of the anilide ring showed 2-fold higher activity against M. tuberculosis than isoniazid and 4.5-fold higher activity against M. avium subsp. paratuberculosis than rifampicin. 6-Hydroxy-N-(2-methylphenyl) naphthalene-2-carboxamide had MIC = 29 mu M against M. avium complex. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT assay. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using the THP-1 cells, and no significant lethal effect was observed. The structure-activity relationships are discussed.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

<a href="/cs/project/EE2.3.30.0053" target="_blank" >EE2.3.30.0053: Farmakotoxikologické hodnocení nově syntetizovaných (izolovaných) látek jako nástroj integrace preklinických disciplín na VFU Brno</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Bioorganic and Medicinal Chemistry

ISSN

0968-0896

e-ISSN

—

Svazek periodika

23

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

2035-2043

Kód UT WoS článku

000352698700013

EID výsledku v databázi Scopus

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