About: Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://www.sciencedirect.com/science/article/pii/S0960894X13004903
Description	To develop new potential antimycobacterial drugs, a series of pyrazinamide derivatives was designed, synthesized and tested for their ability to inhibit the growth of selected mycobacterial strains (Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two strains of Mycobacterium avium). This Letter is focused on binuclear pyrazinamide analogues containing the -CONH-CH2-bridge, namely on N-benzyl-5-chloropyrazine-2-carboxamides with various substituents on the phenyl ring and their comparison with some analogously substituted 5-chloro-N-phenylpyrazine-2-carboxamides. Compounds from the N-benzyl series exerted lower antimycobacterial activity against M. tuberculosis H37Rv then corresponding anilides, however comparable with pyrazinamide (12.5-25 mu g/mL). Remarkably, 5-chloro-N-(4-methylbenzyl)pyrazine-2-carboxamide (8, MIC = 3.13 mu g/mL) and 5-chloro-N-(2-chloro-benzyl)pyrazine-2-carboxamide (1, MIC = 6.25 mu g/mL) were active against M. kansasii, which is naturally unsusceptible to PZA. Basic structure-activity relationships are presented. To develop new potential antimycobacterial drugs, a series of pyrazinamide derivatives was designed, synthesized and tested for their ability to inhibit the growth of selected mycobacterial strains (Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two strains of Mycobacterium avium). This Letter is focused on binuclear pyrazinamide analogues containing the -CONH-CH2-bridge, namely on N-benzyl-5-chloropyrazine-2-carboxamides with various substituents on the phenyl ring and their comparison with some analogously substituted 5-chloro-N-phenylpyrazine-2-carboxamides. Compounds from the N-benzyl series exerted lower antimycobacterial activity against M. tuberculosis H37Rv then corresponding anilides, however comparable with pyrazinamide (12.5-25 mu g/mL). Remarkably, 5-chloro-N-(4-methylbenzyl)pyrazine-2-carboxamide (8, MIC = 3.13 mu g/mL) and 5-chloro-N-(2-chloro-benzyl)pyrazine-2-carboxamide (1, MIC = 6.25 mu g/mL) were active against M. kansasii, which is naturally unsusceptible to PZA. Basic structure-activity relationships are presented. (en)
Title	Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides (en)
skos:prefLabel	Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides (en)
skos:notation	RIV/00216208:11160/13:10145627!RIV14-MZ0-11160___
http://linked.open...avai/riv/aktivita	I P S
http://linked.open...avai/riv/aktivity	I, P(EE2.3.20.0235), P(NT13346), S
http://linked.open...iv/cisloPeriodika	12
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Doležal, Martin Zitko, Jan Kuneš, Jiří Servusová, Barbora Vobicková, Jana Kubíček, Vladimír
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Farmaceutická fakulta v Hradci Králové
http://linked.open...dnocenehoVysledku	109457
http://linked.open...ai/riv/idVysledku	RIV/00216208:11160/13:10145627
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Lipophilicity; Antimycobacterial activity; Anilines; Benzylamines; Pyrazinamide derivatives (en)
http://linked.open.../riv/klicoveSlovo	Anilines Benzylamines Antimycobacterial activity Lipophilicity Pyrazinamide derivatives
http://linked.open...odStatuVydavatele	BR - Brazilská federativní republika
http://linked.open...ontrolniKodProRIV	[B9C70DB78954]
http://linked.open...i/riv/nazevZdroje	Bioorganic and Medicinal Chemistry Letters
http://linked.open...in/vavai/riv/obor	FR
http://linked.open...ichTvurcuVysledku	6 (xsd:int)
http://linked.open...cetTvurcuVysledku	7 (xsd:int)
http://linked.open...vavai/riv/projekt	Design and enzyme targeting of antibacterial active compounds against multidrug resistant strains Establishment of Research Team Focused on Experimental and Applied Biopharmacy
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	23
http://linked.open...iv/tvurceVysledku	Doležal, Martin Kuneš, Jiří Zitko, Jan Kubíček, Vladimír Paterová, Pavla Servusová, Barbora Vobicková, Jana
http://linked.open...ain/vavai/riv/wos	000319268500023
issn	0960-894X
number of pages	3 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.bmcl.2013.04.021
http://localhost/t...ganizacniJednotka	11160

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