IFLP   13074
INSTITUTO DE FISICA LA PLATA
Unidad Ejecutora - UE
artículos
Título:
Crystal structure and anticonvulsant activity of (±)-3,6-Di-O-(2-propylpentanoyl)-1,2:4,5-di-O-isopropylidene-myo-inositol
Autor/es:
S. C. MOON; G. A. ECHEVERRÍA; G. PUNTE; J. ELLENA; L. E. BRUNO-BLANCH
Revista:
CARBOHYDRATE RESEARCH
Referencias:
Año: 2006
ISSN:
0008-6215
Resumen:
The biological activity and crystal structure of (±)-3,6-Di-O-(2-propylpentanoyl)-1,2:4,5-di-O-isopropylidene-myo-inositol have been investigated. This compound shows better anticonvulsant activity than valproic acid in the MES test measured in mice. Its structure, determined from single crystal X-ray diffraction measurements, shows that the inositol ring deviates from the ideal chair conformation and that the two 2-propylpentanoyl groups are located on opposite ring positions. This molecular conformation lets carbonyl and hydroxyl oxygen atoms to be available for hydrogen bonds interactions, hinders carbonyl carbon atoms, preventing metabolic enzymatic hydrolysis and helps to rationalize the observed inactive profile in the PTZ test. The anticonvulsant activity profile suggests a mechanism different from that of VPA.