Synthesis of new analogues of salacinol containing a pendant hydroxymethyl group as potential glycosidase inhibitors |
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Authors: | Nasi Ravindranath Pinto B Mario |
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Affiliation: | Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6. |
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Abstract: | The synthesis of new analogues of the naturally occurring glycosidase inhibitor, salacinol, and its ammonium analogue, ghavamiol is described. These analogues contain an additional hydroxymethyl group at C-1, which was intended to form additional polar contacts within the active site of glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least hindered carbon atom of 2,4-O-benzylidene-l (or d)-erythritol 1,3-cyclic sulfate by 2,5-anhydro-1,3:4,6-di-O-benzylidene-2,5-dideoxy-5-thio (or 1,5-imino)-l-iditol. |
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Keywords: | Glycosidase inhibitors Analogues of salacinol and ghavamiol Ammonium salt Sulfonium salt Cyclic sulfate |
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