title: Studies on pyrazine derivatives. XLVII. Synthesis and antibacterial activity of novel pyrazine derivatives with amidoxime moiety.
abstract: The new pyrazine derivatives exhibiting an antibacterial activity have been synthesized. Initial amidoxime 1 was obtained in the reaction of pyrazinecarbonitrile with hydroxylamine. Upon treatment of amidoxime with methyl iodide O-methyl derivative 2 was formed. Both amidoximes were transformed into imidoyl chlorides 3, 4. Then the chloride atom in those derivatives was substituted with various secondary amines giving appropriate oximes 5-18 and O-methyl-oximes 19 and 20. The obtained compounds were tested in vitro for their tuberculostatic activity. The inhibiting concentration (MIC) values were within 25-100 microg/mL. Their activity towards 25 strains of anaerobic and 25 strains of aerobic bacteria was also studied. Three compounds exhibited activity against both types of bacteria.
authors.affiliation: Department of Organic Chemistry, Medical University of Gdańsk, 107 Al. Gen. Hallera, 80-416 Gdańsk, Poland. katarzyna.gobis@wp.pl
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Gobis
authors.forename: Henryk
authors.initials: H
authors.lastname: Foks
authors.forename: Anna
authors.initials: A
authors.lastname: Kedzia
authors.forename: Maria
authors.initials: M
authors.lastname: Wierzchowska
authors.forename: Ewa
authors.initials: E
authors.lastname: Kwapisz
authors.forename: Zofia
authors.initials: Z
authors.lastname: Zwolska
authors.forename: Ewa
authors.initials: E
authors.lastname: Augustynowicz-Kopeć
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001420:Bacteria, Aerobic / Q000187:drug effects; D001421:Bacteria, Anaerobic / Q000187:drug effects; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010091:Oximes / Q000138:chemical synthesis* / Q000494:pharmacology*; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D010091:Oximes; D011719:Pyrazines