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Synthesis and antibacterial activity of novel pyridine and pyrazine derivatives obtained from amidoximes
Author(s) -
Gobis Katarzyna,
Foks Henryk,
Kędzia Anna,
Wierzbowska Maria,
Zwolska Zofia
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.251
Subject(s) - chemistry , pyridine , pyrazine , antibacterial activity , decarboxylation , methyl iodide , bacteria , organic chemistry , iodide , anaerobic exercise , medicinal chemistry , catalysis , physiology , genetics , biology
The new pyridine, 4‐pyridine N ‐oxide and pyrazine derivatives exhibiting an antibacterial activity have been synthesized. Amidoximes were transformed into N ‐hydroxyimidoyl chlorides and then into appropriate oximes. Upon treatment of pyridinecaboxamidoximes with methyl iodide 1‐methylpyridynium iodides were formed. Reaction of amidoximes with various carbamoyl chlorides led to corresponding 5‐aminocarbonyl‐1,2,4‐oxadiazoles. Some of carboxamides have undergone thermal decarboxylation to tertiary amines. The newly synthesized compounds were tested in vitro for their tuberculostatic activity. MIC of the most active compound 9 was 12.5 μg/mL for H 37 Rv strain. Their activity towards 25 strains of anaerobic and 25 strains of aerobic bacteria was also studied. Derivative 18 was active against both aerobic and anaerobic types of the bacteria. J. Heterocyclic Chem., (2009).