N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F86652079%3A_____%2F16%3A00465898" target="_blank" >RIV/86652079:_____/16:00465898 - isvavai.cz</a>

Alternative codes found

RIV/62157124:16170/16:43874577 RIV/62157124:16370/16:43874577

Result on the web

<a href="http://dx.doi.org/10.3390/molecules21081068" target="_blank" >http://dx.doi.org/10.3390/molecules21081068</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules21081068" target="_blank" >10.3390/molecules21081068</a>

Result language

angličtina

Original language name

N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity

Original language description

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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

EH - Ecology - communities

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

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

Name of the periodical

Molecules

ISSN

1420-3049

e-ISSN

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Volume of the periodical

21

Issue of the periodical within the volume

8

Country of publishing house

CH - SWITZERLAND

Number of pages

18

Pages from-to

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UT code for WoS article

000382334600107

EID of the result in the Scopus database

2-s2.0-84983349265