Synthesis, antimycobacterial and antifungal evaluation of some new 1-ethyl-5-(hetero)aryl-6-styryl-1,6-dihydropyrazine-2,3-dicarbonitriles

Abstract

The Petasis reaction of 6-hydroxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with trans-styrylboronic acids proved to proceed smoothly at room temperature to give the corresponding 5-(hetero)aryl-6-styryl substituted 1,6-dihydropyrazine derivatives. Also it has been found that C(6) unsubstituted 1,6-dihydro- or 1,4,5,6-tetrahydropyrazine derivatives can be easy prepared in high yields from the corresponding pyrazinium salts by reduction with triethylsilane. All synthesized compounds were screened in vitro for their antifungal activities against seven pathogenic fungal strains and antimycobacterial activities against Mycobacterium tuberculosis H37Rv, avium, terrae and multi-drug-resistant strains isolated from tuberculosis patients in the Ural region (Russia).

Keywords: Antifungal activity; Antituberculosis activity; Petasis reaction; Pyrazine; Tuberculosis.