Collect. Czech. Chem. Commun. 1996, 61, 1109-1114

Synthesis and Antituberculotic Activity of 5-Alkyl-6-chloro-2-pyrazinecarboxamides and Corresponding Thioamides

Jiří Hartla, Martin Doležala, Jana Krinkováa, Antonín Lyčkab and Želmíra Odlerovác

a Department of Medicinal Chemistry and Drug Control, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic
b Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví, Czech Republic
c Institute of Preventive and Clinic Medicine, 833 01 Bratislava, Slovak Republic


Homolytic alkylation of 6-chloro-2-pyrazinecarbonitrile by alkanoic acid and subsequent partial hydrolysis afforded 5-alkyl-6-chloro-2-pyrazinecarboxamides 1a-1e. Reaction of amides 1a-1e by Lawesson's reagent afforded corresponding thioamides 2a-2e. The structure of compounds was confirmed by elemental analysis, IR and 1H NMR spectra. The assessment of in vitro antimycobacterial activity of the compounds was carried out. The highest antituberculotic activity against Mycobacterium tuberculosis and other mycobacterial strains in this series was shown by 5-(1,1-dimethylethyl)-6-chloro-2-pyrazinecarbothioamide (2e).

Keywords: Homolytic alkylation; Pyrazinecarboxamides; Pyrazinecarbothioamides; Tuberculostatic activity.