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

J 2015

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

KOS, J, E NEVIN, M SORAL, Ivan KUSHKEVYCH, Tomáš GONĚC et. al.

Basic information

Original name

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

Authors

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

Edition

BIOORGANIC & MEDICINAL CHEMISTRY, OXFORD, PERGAMON-ELSEVIER SCIENCE LTD, 2015, 0968-0896

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10606 Microbiology

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.923

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.bmc.2015.03.018

UT WoS

000352698700013

Keywords in English

Hydroxynaphthalene-2-carboxanilides; In vitro antimycobacterial activity; MTT assay; In vitro cytotoxicity; Structure-activity relationships

Abstract

V originále

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.

Citovat

KOS, J, E NEVIN, M SORAL, Ivan KUSHKEVYCH, Tomáš GONĚC, Pavel BOBÁĽ, Peter KOLLÁR, A COFFEY, O Mahony J, T LIPTAJ, K KRALOVA and J JAMPILEK. Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides. BIOORGANIC & MEDICINAL CHEMISTRY. OXFORD: PERGAMON-ELSEVIER SCIENCE LTD, 2015, vol. 23, No 9, p. 2035-2043. ISSN 0968-0896. Available from: https://dx.doi.org/10.1016/j.bmc.2015.03.018.

@article{1409330,
   author = {Kos, J and Nevin, E and Soral, M and Kushkevych, Ivan and Goněc, Tomáš and Bobáľ, Pavel and Kollár, Peter and Coffey, A and J, O Mahony and Liptaj, T and Kralova, K and Jampilek, J},
   article_location = {OXFORD},
   article_number = {9},
   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},
   language = {eng},
   issn = {0968-0896},
   journal = {BIOORGANIC & MEDICINAL CHEMISTRY},
   note = {Doc. Kushkevychovi chybí na WoS afiliace na MU, nelze přenášet do RIV!},
   title = {Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides},
   url = {http://dx.doi.org/10.1016/j.bmc.2015.03.018},
   volume = {23},
   year = {2015}
}

TY  - JOUR
ID  - 1409330
AU  - 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
PY  - 2015
TI  - Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides
JF  - BIOORGANIC & MEDICINAL CHEMISTRY
VL  - 23
IS  - 9
SP  - 2035-2043
EP  - 2035-2043
PB  - PERGAMON-ELSEVIER SCIENCE LTD
SN  - 09680896
N1  - Doc. Kushkevychovi chybí na WoS afiliace na MU, nelze přenášet do RIV!
KW  - Hydroxynaphthalene-2-carboxanilides
KW  - In vitro antimycobacterial activity
KW  - MTT assay
KW  - In vitro cytotoxicity
KW  - Structure-activity relationships
UR  - http://dx.doi.org/10.1016/j.bmc.2015.03.018
L2  - http://dx.doi.org/10.1016/j.bmc.2015.03.018
N2  - 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.
ER  -

KOS, J, E NEVIN, M SORAL, Ivan KUSHKEVYCH, Tomáš GONĚC, Pavel BOBÁĽ, Peter KOLLÁR, A COFFEY, O Mahony J, T LIPTAJ, K KRALOVA and J JAMPILEK. Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides. \textit{BIOORGANIC \&{}amp; MEDICINAL CHEMISTRY}. OXFORD: PERGAMON-ELSEVIER SCIENCE LTD, 2015, vol.~23, No~9, p.~2035-2043. ISSN~0968-0896. Available from: https://dx.doi.org/10.1016/j.bmc.2015.03.018.

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