About: Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution

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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/S0960894X12015041
Description	A series of 19 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro whole cell antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two types of Mycobacterium avium. The series consisted of 3( benzylamino)-5-cyanopyrazine-2-carboxamides and 3-(benzylamino)pyrazine-2,5-dicarbonitriles with various substituents on the phenyl ring. RP-HPLC method was used to determine the lipophilicity of the prepared compounds. Nine compounds exerted similar or better activity against Mycobacterium tuberculosis compared to pyrazinamide (MIC = 6.25-12.5 mu g/mL). 3-(Benzylamino)pyrazine-2,5-dicarbonitrile inhibited all of the tested mycobacterial strains with MIC within the range 12.5-25 mu g/mL. Although not the most active, 4-NH2 substituted compounds possessed the lowest in vitro cytotoxicity (hepatotoxicity), leading to selectivity index SI = 5.5 and SI > 21. A series of 19 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro whole cell antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two types of Mycobacterium avium. The series consisted of 3( benzylamino)-5-cyanopyrazine-2-carboxamides and 3-(benzylamino)pyrazine-2,5-dicarbonitriles with various substituents on the phenyl ring. RP-HPLC method was used to determine the lipophilicity of the prepared compounds. Nine compounds exerted similar or better activity against Mycobacterium tuberculosis compared to pyrazinamide (MIC = 6.25-12.5 mu g/mL). 3-(Benzylamino)pyrazine-2,5-dicarbonitrile inhibited all of the tested mycobacterial strains with MIC within the range 12.5-25 mu g/mL. Although not the most active, 4-NH2 substituted compounds possessed the lowest in vitro cytotoxicity (hepatotoxicity), leading to selectivity index SI = 5.5 and SI > 21. (en)
Title	Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution (en)
skos:prefLabel	Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution (en)
skos:notation	RIV/00216208:11160/13:10131279!RIV14-MZ0-11160___
http://linked.open...avai/riv/aktivita	I P S
http://linked.open...avai/riv/aktivity	I, P(EE2.3.30.0022), P(NT13346), S
http://linked.open...iv/cisloPeriodika	2
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Doležal, Martin Zitko, Jan Kuneš, Jiří Mandíková, Jana Trejtnar, František 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	109458
http://linked.open...ai/riv/idVysledku	RIV/00216208:11160/13:10131279
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Cytotoxicity; Pyrazinamide derivatives; Lipophilicity; Benzylamines; Antimycobacterial activity (en)
http://linked.open.../riv/klicoveSlovo	Benzylamines Cytotoxicity Antimycobacterial activity Lipophilicity Pyrazinamide derivatives
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[C03B9E54EAD1]
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 Support of establishment, development, and mobility of quality research teams at the Charles University
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	23
http://linked.open...iv/tvurceVysledku	Doležal, Martin Kuneš, Jiří Zitko, Jan Mandíková, Jana Trejtnar, František Kubíček, Vladimír Paterová, Pavla
http://linked.open...ain/vavai/riv/wos	000312959600018
issn	0960-894X
number of pages	4 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.bmcl.2012.11.052
http://localhost/t...ganizacniJednotka	11160

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