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  • Title: Synthesis of novel sigma-receptor ligands from methyl alpha-D-mannopyranoside.
    Author: Wiedemeyer K, Wünsch B.
    Journal: Carbohydr Res; 2006 Oct 16; 341(14):2321-34. PubMed ID: 16854396.
    Abstract:
    For the first time a monosaccharide (methyl alpha-D-mannopyranoside) has been used as starting material for the synthesis of novel sigma-receptor ligands. The hept-3-ulopyranoside dimethyl ketals 14 and 15 were obtained from the nitrile 7 via two synthetic routes. After selective hydrolysis of the ketone dimethyl acetal, various amino substituents were introduced into position 3. High sigma(1)-receptor affinity and selectivity was attained with equatorially arranged amino substituents in position 3 and a dichlorophenylacetamide moiety in position 7. The anomeric mixture of dimethylamines 26alpha/beta displayed the highest sigma(1)-receptor affinity (K(i)=21nM) within this small series of test compounds.
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