INQUINOA   21218
INSTITUTO DE QUIMICA DEL NOROESTE
Unidad Ejecutora - UE
artículos
Título:
Synthesis and antibacterial activity of highly oxygenated 1,8-cineole derivatives
Autor/es:
M. B. VILLECCO, J. V. CATALÁN, M. I. VEGA, F. M. GARIBOTTO, R. D. ENRIZ, CÉSAR A. N. CATALÁN
Revista:
NATURAL PRODUCT COMMUNICATIONS
Editorial:
NATURAL PRODUCT COMMUNICATIONS INC.
Referencias:
Año: 2008 vol. 3 p. 303 - 312
Resumen:
Abstract- Seventeen mono-, di- and trifunctionalized 1,8-cineole derivatives carrying OH, OAc, keto and lactone functions at C-5, C-8 and C-9 were synthesized from 1,8-cineole with fair to excellent yields. The antibacterial activity of these synthetic compounds against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus using agar dilution method was examined. Lactones 1,3-dimethyl-2-oxabicyclo[2.2.2]octan-8-endo-acetyloxy-5¨9-olide (15) and 1,3-dimethyl-2-oxabicyclo[2.2.2]octan-8-endo-ol-5¨9-olide (16) showed the highest antibacterial activity against all the three Gram negative bacteria assayed. A structure-activity relationship (SAR) study on the oxygenated 1,8-cineole derivatives have allowed a model to be proposed for the recognition of the minimal structural requirements for the antimicrobial effect. Keywords: 1-8-cineole derivatives, synthesis, antibacterial activity, structure-activity relationship (SAR) study.