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Note | Regular issue | Vol 68, No. 12, 2006, pp.2615-2626
Published online, 24th October, 2006
DOI: 10.3987/COM-06-10867
Studies on Pyrazine Derivatives. XLIX. Synthesis and Antibacterial Activity of 6-Methoxypyrazine-2-carboxylic Acid Hydrazide Derivatives

Katarzyna Gobis,* Henryk Foks, Aleksandra Zuralska, and Anna Kedzia

*Department of Organic Chemistry, Medical University of Gdansk, Al. Gen. Hallera 107, 80-416 Gdansk, Poland

Abstract

The new 6-methoxy-pyrazine derivatives have been synthesized. 6-Methoxy-pyrazine-2-carboxylic acid hydrazide was used as an initial material to obtain mono- and dithioester of hydrazinecarbodithioic acid (2 and 3). Compound (2) in reaction with ethanolamine gave triazole derivative (8) with β-hydoxyethyl substituent in 4-position and hydroxyl group in 6-position of pyrazine ring. Dithioester (3) in a reaction with morpholine cyclized to 1,3,4-oxadiazole (11). The same substrate with alkyldiamines gave the few following derivatives: 1,3-diazacycloalkane derivatives (9 and 10), S-methyl-1,3,4-oxadiazole derivative (12) and 1,2,4-triazoletetrahydropyrimidine (13). The compounds obtained were tested in vitro for their activity towards pathogenic strains of anaerobic and aerobic bacteria. Derivative (9) was the most active against both types of tested strains.