Tetrazole regioisomers in the development of nitro group-containing antitubercular agents

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F15%3A10312842" target="_blank" >RIV/00216208:11160/15:10312842 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60162694:G44__/15:43875343 RIV/00179906:_____/15:10312842

Výsledek na webu

<a href="http://pubs.rsc.org/en/content/articlehtml/2015/md/c4md00301b" target="_blank" >http://pubs.rsc.org/en/content/articlehtml/2015/md/c4md00301b</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c4md00301b" target="_blank" >10.1039/c4md00301b</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Tetrazole regioisomers in the development of nitro group-containing antitubercular agents

Popis výsledku v původním jazyce

Tetrazole derivatives containing nitro substituents have been identified as promising antitubercular agents. In this study, the antitubercular potency, selectivity and toxicity of tetrazole 1,5- and 2,5-regioisomers were examined. We prepared a series of1-and 2-alkyl-5-benzylsulfanyl-2H-tetrazoles and their selenium analogs with various nitro group substitutions. These 1,5-and 2,5-regioisomers were isolated and unambiguously identified using H-1 and/or C-13 NMR. Among the prepared compounds, 1-and 2-alkyl-5-[(3,5-dinitrobenzyl) sulfanyl]-2H-tetrazole derivatives and their selenium bioisosteres showed the highest antimycobacterial activity, with minimal inhibitory concentration (MIC) values of approximately 1 mu M (0.37-0.46 mu g mL(-1)) against Mycobacterium tuberculosis CNCTC My 331/88. The 2-alkyl regioisomers exhibited consistently higher antimycobacterial activity and lower in vitro toxicity against a mammalian cell line compared to the 1-alkyl isomers. The antimycobacterial activ

Název v anglickém jazyce

Tetrazole regioisomers in the development of nitro group-containing antitubercular agents

Popis výsledku anglicky

Tetrazole derivatives containing nitro substituents have been identified as promising antitubercular agents. In this study, the antitubercular potency, selectivity and toxicity of tetrazole 1,5- and 2,5-regioisomers were examined. We prepared a series of1-and 2-alkyl-5-benzylsulfanyl-2H-tetrazoles and their selenium analogs with various nitro group substitutions. These 1,5-and 2,5-regioisomers were isolated and unambiguously identified using H-1 and/or C-13 NMR. Among the prepared compounds, 1-and 2-alkyl-5-[(3,5-dinitrobenzyl) sulfanyl]-2H-tetrazole derivatives and their selenium bioisosteres showed the highest antimycobacterial activity, with minimal inhibitory concentration (MIC) values of approximately 1 mu M (0.37-0.46 mu g mL(-1)) against Mycobacterium tuberculosis CNCTC My 331/88. The 2-alkyl regioisomers exhibited consistently higher antimycobacterial activity and lower in vitro toxicity against a mammalian cell line compared to the 1-alkyl isomers. The antimycobacterial activ

Druh

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

CEP obor

FR - Farmakologie a lékárnická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA14-08423S" target="_blank" >GA14-08423S: Studie vztahů struktura-aktivita-toxicita ve skupině nízkomolekulárních sloučenin s antimykobacterialní aktivitou</a><br>

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

MedChemComm

ISSN

2040-2503

e-ISSN

—

Svazek periodika

6

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

174-181

Kód UT WoS článku

000349700400018

EID výsledku v databázi Scopus

2-s2.0-84920391799