Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: synthesis and biological activity.

Research paper by M M Dolezal, J J Jampílek, Z Z Osicka, J J Kunes, V V Buchta, P P Víchová

Indexed on: 24 Oct '03Published on: 24 Oct '03Published in: Farmaco (Societa chimica italiana : 1989)


Homolytic aroylation of pyrazine nucleus with various substituted aromatic carbaldehydes afforded a series of 5-aroylpyrazine-2-carboxylic acid derivatives. The synthetic approach, analytical and spectroscopic data of all compounds synthesized, their preliminary in vitro evaluation of antituberculotic and antifungal activities, cytotoxicity data and subsequent SAR studies are presented. Among all derivatives prepared, only 5-(4-chlorobenzoyl)-pyrazine-2-carbothioamide (3d) showed promising activity (90% inhibition) against Mycobacterium tuberculosis. The highest antifungal effect (MIC<1.95 microM ml(-1)) against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-benzoylpyrazine-2-carbothioamide (3a). Thioamides exhibited higher in vitro antimicrobial activity than the corresponding amides.