Facile, alternative route to lubeluzole, its enantiomer, and the racemate |
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Authors: | Bruno Claudio Carocci Alessia Catalano Alessia Cavalluzzi Maria M Corbo Filomena Franchini Carlo Lentini Giovanni Tortorella Vincenzo |
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Institution: | Dipartimento Farmaco-Chimico, Facoltà di Farmacia, Università degli Studi di Bari, Bari, Italy. |
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Abstract: | Lubeluzole (S)-9] has been synthesized by a convergent synthesis, alkylation of N-methyl-N-piperidin-4-yl-1,3-benzothiazol-2-amine (4) with (+)-(R)-1-chloro-3-(3,4-difluorophenoxy)propan-2-ol (+)-(R)-8] being the key step. Alcohol (+)-(R)-8 was obtained from commercially available (R)-epichlorohydrin (R)-6], while the thiazole derivative 4 was easily obtained starting from N-protected piperidin-4-one (1) in a three-step procedure. The same method was used in order to obtain both the (R)-stereoisomer of lubeluzole (R)-9] and its racemate (RS)-9]. Overall yields ranged from 20% to 35%. The enantiomeric excess values for (S)-9 and (R)-9 were 97% and 94% respectively, as analyzed by chiral HPLC. |
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Keywords: | stroke sodium channel stereospecific synthesis enantiomers enantiomeric excess |
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