Crystal structure of (±)-3,6-Di-O-(2-propylpentanoyl)-1,2:4,5-di-O-isopropylidene-myo-inositol, an anticonvulsant agent

SUNG MOON; GUSTAVO ECHEVERRÍA; JAVIER ELLENA; GRACIELA PUNTE; LUIS BRUNO-BLANCH

CARBOHYDRATE RESEARCH

Elsevier

Año: 2007 vol. 342 p. 1456 - 1461

0008-6215

The biological activity and cristal structure of (±)-1,2:4,5-di-O-isopropylidene-3,6-di-O-(2-propylpentanoyl)-myo-inositol have been investigated. This compound shows better anticonvulsant activity than valproic acid (VPA) in the MES test as 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-bonding 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.