An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3- azabicyclo[3.2.1]octane-6-carboxylic acids |
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Authors: | Gelmi Maria Luisa Cattaneo Cristian Pellegrino Sara Clerici Francesca Montali Marina Martini Claudia |
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Institution: | Istituto di Chimica Organica A. Marchesini, Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20133 Milano, Italy. marialuisa.gelmi@unimi.it |
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Abstract: | A single-step synthesis on a gram scale of four pure stereoisomers of the 6-amino-3-azabicyclo3.2.1]octane-6-carboxylic acid was carried out using (R)-1-phenylethylamine to confer chirality. The phenylethyl group, and the p-methoxy group linked to the N-atom, are easily removed by hydrogenolysis to afford the corresponding NH-3 derivatives. A series of N-3-alkyl compounds were prepared by way of a "one-pot" deprotection-alkylation procedure starting from the above key compounds. Their biological activity has been evaluated on the GABA receptor. |
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