Journal
HETEROCYCLIC COMMUNICATIONS
Volume 20, Issue 4, Pages 215-223Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/hc-2014-0107
Keywords
acidity; antibacterial activity; DFT quantum chemical calculations; isoxazolo[3,4-b]pyridin-3(1H)-one; N-alkylation; mesomerism
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Funding
- Polish Ministry of Science and Higher Education
- National Science Centre [IP2012 055472]
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The electronic structure and prototropic tautomerism of 4,6-dimethylisoxazolo[3,4-b]pyridin-3(1H)-one (1) were studied theoretically with use of the B3LYP/6-31G* and omega B97X-D/6-31G* density functional methods and SM8 (H2O, DMF) solvation models. Compound 1, which is a weak acid with a pK(a) of 6.9, undergoes regioselective alkylation and sulfonylation under basic reaction conditions to give a series of N1-substituted products 2a-i. Later compounds were evaluated in vitro for antibacterial activity with the use of 68 strains of aerobic and anaerobic bacteria, including 12 reference strains.
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