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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00179906%3A_____%2F13%3A10145627" target="_blank" >RIV/00179906:_____/13:10145627 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11160/13:10145627

Výsledek na webu

<a href="http://www.sciencedirect.com/science/article/pii/S0960894X13004903" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0960894X13004903</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bmcl.2013.04.021" target="_blank" >10.1016/j.bmcl.2013.04.021</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 (12.5-25mu 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 unsuscepti

Název v anglickém jazyce

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

Popis výsledku anglicky

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 (12.5-25mu 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 unsuscepti

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

FR - Farmakologie a lékárnická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Bioorganic and Medicinal Chemistry Letters

ISSN

0960-894X

e-ISSN

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Svazek periodika

23

Číslo periodika v rámci svazku

12

Stát vydavatele periodika

BR - Brazilská federativní republika

Počet stran výsledku

3

Strana od-do

3589-3591

Kód UT WoS článku

000319268500023

EID výsledku v databázi Scopus

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