Synthesis of N-substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols: Search for new glycosidase inhibitors
N-Substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols 9 and 10, respectively, were derived from (+)-L- and (-)-D-tartaric acid, respectively. Compounds 9k, 91, and 9m with the N-substituents, BnNH(CH2)(2), 4-Phc(6)H(4)CH(2)NH(CH2)(2) and 4-ClC6H4CH2NH(CH2)(2), respectively, showed modest inhibitory activities toward aD-amyloglucosidases from Aspergillus niger and from Rhizopus mold (Table 1). Unexpectedly, several (3R,4R)-pyrrolidine-3,4-diols 10 showed inhibitory activities toward alpha-D-mannosidases from almonds and from jack bean (Table 3). N-Substitution by the NH2(CH2)(2) group, i.e., 10g, led to the highest potency.
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Keywords: Immunodeficiency-virus type-1 ; hyacinthoides-non-scripta ; hiv entry ; inhibitors ; tartaric acid ; asymmetric hydrogenation ; envelope ; glycoprotein ; glucosidase inhibitor ; morus-alba ; derivatives ; alkaloids
Ecole Polytech Fed Lausanne, Lab Glyochim & Synth Asymetr, BCH, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08