Publication details

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

Authors

KOS J NEVIN E SORAL M KUSHKEVYCH Ivan GONĚC Tomáš BOBÁĽ Pavel KOLLÁR Peter COFFEY A J O Mahony LIPTAJ T KRALOVA K JAMPILEK J

Year of publication 2015
Type Article in Periodical
Magazine / Source BIOORGANIC & MEDICINAL CHEMISTRY
MU Faculty or unit

Faculty of Science

Citation
Web http://dx.doi.org/10.1016/j.bmc.2015.03.018
Doi http://dx.doi.org/10.1016/j.bmc.2015.03.018
Keywords Hydroxynaphthalene-2-carboxanilides; In vitro antimycobacterial activity; MTT assay; In vitro cytotoxicity; Structure-activity relationships
Description 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. (C) 2015 Elsevier Ltd. All rights reserved.

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