Synthesis of tri-and tetramines containing two 2,3-dihydroxypyrrolidine moieties and their inhibitory activity toward alpha-mannosidases
Through the reductive amination of N-[(tert-butoxy) carbonyl]-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose with tetramethylenediamine, hexamethylenediamine, 2,7-diaminofluorene, 4,4'-diaminodiphenylmethane and 1,4-(diaminomethyl) benzene, five tetramines containing two (2R, 3R, 4S)-2-aminomethylpyrrolidine- 3,4- diol moieties have been prepared and assayed for their inhibitory activities toward 24 glycosidases. Tetramines containing the tetramethylene or benzene-1,4-dimethylene linkers are more potent amannosidase inhibitors than simple (2R, 3R, 4S)-2-aminomethylpyrrolidine- 3,4-diols. Triamines such as (2S, 3R, 4S)-bis(3,4-dihydroxy-pyrrolidin-2-ethyl) amine were also prepared and shown to be better alpha-mannosidase inhibitors than (2S, 3R, 4S)- 2-(2-aminoethyl) pyrrolidin-3,4-diol.
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Keywords: 3 deoxy derivatives ; glycosidase inhibitors ; mannostatin-a ; biologicalevaluation ; n-butyldeoxynojirimycin ; advanced malignancies ; processinginhibitor ; potent ; swainsonine ; galactosidase
Record created on 2005-11-09, modified on 2016-08-08