M. G. Bogdanov, M. Palamareva, B. Gocheva
May 1, 2007
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0
Influential Citations
12
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Journal
Journal of Heterocyclic Chemistry
Abstract
The reaction between homophthalic anhydride and cyclohexanone was examined both in the presence of DMAP or BF3·Et2O complex as a catalyst. The latter yielded (±)-1-oxo-1H-spiro[benzo[c]pyran-3(4H), 1′-cyclohexane]-4-carboxylic acid (3) in a higher yield (82 %). A series of new (±)-4-(N,N-disubstituted-1-carbamoyl)-1H-spiro[benzo[c]pyran-3(4H),1′-cyclohexane]-1-ones (5a-h) were synthesized from the parent acid 3 by a two-step reaction. Differentiating microbial screening was performed for most of the synthesized compounds against twelve microorganisms belonging to different taxonomic groups. The spiro acid 3 was active against all bacterial strains with MIC ≥ 20 μg/ml against B. subtillis and P. vulgaris. E. coli was the most sensitive strain to the antibacterial effect of the tested compounds.