PMID: 11902648Mar 21, 2002Paper

Synthesis and biological activity of 5-alkyl-6-(alkylsulfanyl)- or 5-alkyl-6-(arylsulfanyl)pyrazine-2-carboxamides and corresponding thioamides

Il Farmaco
Jana KrinkováMilan Pour

Abstract

Nucleophilic substitution of chlorine in 5-alkyl-6-chloropyrazine-2-carboxamides with various alkyl and arylthiolates afforded 20 5-alkyl-6-(alkylsulfanyl)- and 5-alkyl-6-(arylsulfanyl)pyrazine-2-carboxamides. The reaction of the amides with Lawesson's reagent yielded the corresponding thioamides. The assessment of in vitro antimycobacterial and antifungal activity of the compounds was carried out. In both series, the antimycobacterial activity increases with increasing molecular weight of the alkylsulfanyl group in position 6 of the pyrazine ring. Thioamides exhibited higher activity than the corresponding amides. 5-Butyl-6-(phenylsulfanyl)pyrazine-2-carbothioamide (2j) possessed the highest activity (91% inhibition) against Mycobacterium tuberculosis and also the highest lipophilicity (log P = 4.95). Only a poor in vitro antifungal effect was noted in 5-butyl-6-(butylsulfanyl)pyrazine-2-carboxamide (1i) and 6-(ethylsulfanyl)-5-isobutylpyrazine-2-carbothioamide (2q) against Trichophyton mentagrophytes and Absidia corymbifera.

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Citations

Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·R Alan HowieEdward R T Tiekink
Mar 24, 2011·Future Medicinal Chemistry·Prem M S ChauhanMoni Sharma
Nov 26, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Veronika OpletalovaMarta Kucerova-Chlupacova
Jan 15, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marta Kucerova-ChlupacovaVeronika Opletalova
Sep 18, 2007·Chemical Reviews·Turan OzturkOlcay Mert

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