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Titolo:
Chiral resolution of the enantiomers of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide using high-performance liquid chromatography on cellulose-based chiral stationary phases
Autore:
Cannazza, G; Braghiroli, D; Baraldi, M; Parenti, C;
Indirizzi:
Univ Modena & Reggio Emilia, Dipartimento Sci Farmaceut, I-41100 Modena, Italy Univ Modena & Reggio Emilia Modena Italy I-41100 , I-41100 Modena, Italy Univ G DAnnunzio, Dipartimento Sci Farm, I-66013 Chieti, Italy Univ G DAnnunzio Chieti Italy I-66013 to Sci Farm, I-66013 Chieti, Italy
Titolo Testata:
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
fascicolo: 1, volume: 23, anno: 2000,
pagine: 117 - 125
SICI:
0731-7085(20000801)23:1<117:CROTEO>2.0.ZU;2-I
Fonte:
ISI
Lingua:
ENG
Soggetto:
RECEPTOR DESENSITIZATION; TRIS(3,5-DIMETHYLPHENYLCARBAMATE); CYCLOTHIAZIDE; S,S-DIOXIDE; HPLC;
Keywords:
benzothiadiazine; enantioseparation; cellulose-based chiral stationary phases; enantiomerization; semipreparative enantioseparation;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
18
Recensione:
Indirizzi per estratti:
Indirizzo: Cannazza, G Univ Modena & Reggio Emilia, Dipartimento Sci Farmaceut, Via Campi 183, I-41100 Modena, Italy Univ Modena & Reggio Emilia Via Campi 183 Modena Italy I-41100
Citazione:
G. Cannazza et al., "Chiral resolution of the enantiomers of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide using high-performance liquid chromatography on cellulose-based chiral stationary phases", J PHARM B, 23(1), 2000, pp. 117-125

Abstract

Analytical high-performance liquid chromatography (HPLC) methods using derivatized cellulose chiral stationary phases (CSPs) were developed for the separation of the enantiomers of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide ((+/-) IDRA21). in previous studies, (+/-) IDRA21 has been found to have an interesting inhibitory effect on the desensitization of alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid (AMPA) receptor and improve cognition in animals. This compound posses one chiral carbon atom, but very little information has been reported on the stereoselectivity of his activity. Therefore resolution of the enantiomers of this compound and subsequent identification of stereospecifity in his pharmacological actions are clearly matters of interest. The resolution were made under normal- and reversed-phase conditions using a mobile phase consistingof n-hexane:2-propanol (70/30, v/v) and water:acetonitrile (60/40, v/v) respectively, and a CSP of silica-based cellulose tris-3,5-dimethyl-phenylcarbammate (Chiralcel OD and Chiracel OD-R). The enantiomeric nature of eluates was confirmed by circular dichroism (CD) spectra. A baseline separation (R-s > 1.5) was obtained in both cases. Furthemore the isolation of optical isomers of (+/-) IDRA21 was perfomed using a semipreparative column packed with the same cellulose OD CSP. (C) 2000 Elsevier Science B.V. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 07/07/20 alle ore 20:41:16