Antifungal Properties of Some Arylsulfanylpyrazine-2-carboxylic Acid Derivatives

Josef Jampílek¹, Martin Doležal² (dolezalm@faf.cuni.cz), Lukáš Palek², Luís Silva³, Vladimír Buchta³

¹ Zentiva a. s., U Kabelovny 130, 102 37 Prague, Czech Republic
² Department of Pharmaceutical Chemistry and Drug Control, ³ Department of Biological and Medical Sciences, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Czech Republic

Summary

Three possible regioisomers of 6-chloropyrazine- or 5-chloropyrazine- or 3-chloropyrazine-2-carboxylic acid derivatives were generated by means of novel regioselective synthetic and separating methods, developed at our workplace. These C₍₆₎ or C₍₅₎ or C₍₃₎ chlorinated pyrazine derivatives were consequently coupled with 4- or 3-methoxybenzene-1-thiols in the presence of a heterogeneous copper catalyst. Obtained 6- or 5- or 3-(4-methoxyphenyl)- and 6- or 5- or 3-(3-methoxyphenyl)sulfanylpyrazine-2-carboxylic acid derivatives were tested for their antifungal activity against eight fungal strains. Some of them showed only some moderate activities especially against Trichophyton mentagrophytes and Candida albicans (their MIC values ranged from 31.25 to 500 µmol.dm^-3).