Enantioseparation, absolute configuration determination, and anticonvulsant activity of (+/-)-1-(4-aminophenyl)-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-2,3-benzodiazepin-4-one.
The resolution of 1-(4-aminophenyl)-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-benzodiazepin-4-one (+/-)-(R,S)-2 was accomplished by chiral HPLC. The absolute configuration of (+)-2, determined by X-ray crystallographic analysis, was R. The in vivo anticonvulsant activity of the enantiomers (+)-(R)-2 and (-)-(S)-2 is reported. It has been also demonstrated that compound (+/-)-(R,S)-2 in vivo undergoes oxidative metabolism to derivative 1.
Calabrò
Maria Luisa
ML
Dipartimento Farmaco-Chimico, Università di Messina, Messina, Italy.
Raneri
Daniela
D
Ficarra
Paola
P
Ferreri
Guido
G
De Sarro
Giovambattista
G
Bruno
Giuseppe
G
Zappalà
Maria
M
Micale
Nicola
N
Grasso
Silvana
S
D000818:Animals; D000927:Anticonvulsants / Q000737:chemistry* / Q000494:pharmacology; D001570:Benzodiazepinones / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D051381:Rats; D017207:Rats, Sprague-Dawley; D013237:Stereoisomerism
C516046:1-(4-aminophenyl)-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-2,3-benzodiazepin-4-one; D000927:Anticonvulsants; D001570:Benzodiazepinones