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Molecules 2014, 19(4), 3851-3868; doi:10.3390/molecules19043851

N-Substituted 2-Isonicotinoylhydrazinecarboxamides — New Antimycobacterial Active Molecules

Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, SI-1000 Ljubljana, Slovenia
Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské náměstí 7, 702 00 Ostrava, Czech Republic
Authors to whom correspondence should be addressed.
Received: 28 February 2014 / Revised: 21 March 2014 / Accepted: 24 March 2014 / Published: 28 March 2014
(This article belongs to the Section Medicinal Chemistry)
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This report presents a new modification of the isoniazid (INH) structure linked with different anilines via a carbonyl group obtained by two synthetic procedures and with N-substituted 5-(pyridine-4-yl)-1,3,4-oxadiazole-2-amines prepared by their cyclisation. All synthesised derivatives were characterised by IR, NMR, MS and elemental analyses and were evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium avium 330/88, Mycobacterium kansasii 235/80 and one clinical isolated strain of M. kansasii 6509/96. 2-Isonicotinoyl-N-(4-octylphenyl)hydrazinecarboxamide displayed an in vitro efficacy comparable to that of INH for M. tuberculosis with minimum inhibitory concentrations (MICs) of 1–2 μM. Among the halogenated derivatives, the best anti-tuberculosis activity was found for 2-isonicotinoyl-N-(2,4,6-trichlorophenyl)hydrazinecarboxamide (MIC = 4 μM). In silico modelling on the enoyl-acyl carrier protein reductase InhA confirmed that longer alkyl substituents are advantageous for the interactions and affinity to InhA. Most of the hydrazinecarboxamides, especially those derived from 4-alkylanilines, exhibited significant activity against INH-resistant nontuberculous mycobacteria. View Full-Text
Keywords: InhA inhibition; in silico docking; in vitro antimycobacterial activity; 2-isonicotinoylhydrazinecarboxamide; 5-(pyridine-4-yl)-1,3,4-oxadiazol-2-amine; tuberculosis InhA inhibition; in silico docking; in vitro antimycobacterial activity; 2-isonicotinoylhydrazinecarboxamide; 5-(pyridine-4-yl)-1,3,4-oxadiazol-2-amine; tuberculosis

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Rychtarčíková, Z.; Krátký, M.; Gazvoda, M.; Komlóová, M.; Polanc, S.; Kočevar, M.; Stolaříková, J.; Vinšová, J. N-Substituted 2-Isonicotinoylhydrazinecarboxamides — New Antimycobacterial Active Molecules. Molecules 2014, 19, 3851-3868.

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