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Statements

Subject Item
n2:RIV%2F62157124%3A16370%2F12%3A43871112%21RIV13-MSM-16370___
rdf:type
skos:Concept n9:Vysledek
dcterms:description
A series of 14 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and two types of Mycobacterium avium. The series comprised of N-substituted 3-aminopyrazine- 2,5-dicarbonitriles derived from 3-chloropyrazine-2,5-dicarbonitrile by nucleophilic substitution of chlorine by various non-aromatic amines (alkylamines, cycloalkylamines and heterocyclic amines). Noteworthy antimycobacterial activity against M. tuberculosis was found among the alkylamino derivatives, for example, 3-(heptylamino) pyrazine-2,5-dicarbonitrile inhibited M. tuberculosis at MIC = 51 mu mol/L. 3-(Hexylamino) pyrazine-2,5-dicarbonitrile inhibited M. kansasii at MIC = 218 mu mol/L. Basic structure-activity relationships are discussed. A comparison between calculated and experimentally determined lipophilicity parameters within the series is included. A series of 14 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and two types of Mycobacterium avium. The series comprised of N-substituted 3-aminopyrazine- 2,5-dicarbonitriles derived from 3-chloropyrazine-2,5-dicarbonitrile by nucleophilic substitution of chlorine by various non-aromatic amines (alkylamines, cycloalkylamines and heterocyclic amines). Noteworthy antimycobacterial activity against M. tuberculosis was found among the alkylamino derivatives, for example, 3-(heptylamino) pyrazine-2,5-dicarbonitrile inhibited M. tuberculosis at MIC = 51 mu mol/L. 3-(Hexylamino) pyrazine-2,5-dicarbonitrile inhibited M. kansasii at MIC = 218 mu mol/L. Basic structure-activity relationships are discussed. A comparison between calculated and experimentally determined lipophilicity parameters within the series is included.
dcterms:title
Synthesis and antimycobacterial evaluation of N-substituted 3-aminopyrazine-2,5-dicarbonitriles Synthesis and antimycobacterial evaluation of N-substituted 3-aminopyrazine-2,5-dicarbonitriles
skos:prefLabel
Synthesis and antimycobacterial evaluation of N-substituted 3-aminopyrazine-2,5-dicarbonitriles Synthesis and antimycobacterial evaluation of N-substituted 3-aminopyrazine-2,5-dicarbonitriles
skos:notation
RIV/62157124:16370/12:43871112!RIV13-MSM-16370___
n9:predkladatel
n10:orjk%3A16370
n3:aktivita
n4:P n4:I n4:V n4:Z n4:S
n3:aktivity
I, P(NS10367), S, V, Z(MSM0021620822)
n3:cisloPeriodika
4
n3:dodaniDat
n15:2013
n3:domaciTvurceVysledku
n14:9033793
n3:druhVysledku
n5:J
n3:duvernostUdaju
n11:S
n3:entitaPredkladatele
n18:predkladatel
n3:idSjednocenehoVysledku
172910
n3:idVysledku
RIV/62157124:16370/12:43871112
n3:jazykVysledku
n19:eng
n3:klicovaSlova
Structure-activity relationships; Pyrazinamide derivatives; Lipophilicity; Antimycobacterial activity; Alkyl chain homology
n3:klicoveSlovo
n6:Alkyl%20chain%20homology n6:Antimycobacterial%20activity n6:Lipophilicity n6:Structure-activity%20relationships n6:Pyrazinamide%20derivatives
n3:kodStatuVydavatele
NL - Nizozemsko
n3:kontrolniKodProRIV
[7F7A00F06E29]
n3:nazevZdroje
Bioorganic and Medicinal Chemistry Letters
n3:obor
n21:FR
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
6
n3:projekt
n7:NS10367
n3:rokUplatneniVysledku
n15:2012
n3:svazekPeriodika
22
n3:tvurceVysledku
Jampílek, Josef Doležal, Martin Zitko, Jan Kuneš, Jiří Dobrovolný, Lukáš Svobodová, Michaela
n3:wos
000300404900022
n3:zamer
n16:MSM0021620822
s:issn
0960-894X
s:numberOfPages
4
n17:doi
10.1016/j.bmcl.2011.12.129
n20:organizacniJednotka
16370