Synthesis of new heparinoids with high anticoagulant activity

Publisher Website
Google Scholar
Abstract
New heparinoids were synthesized by the chemical method starting from ring-opening polymerization of anhydro sugar derivatives. Sulfation of synthetic (1 .fwdarw. 6)-.alpha.-linked 3-amino-3-deoxy-D-glucopyran and its copolymers gave dextran-type heparinoids having a sulfamide group on the C-3 carbon of the sugar unit. Heparinoids with different sulfamide contents indicated that the anticoagulant activity (35.3-41.3 units/mg) is independent of the sulfamide content, while an increase in sulfamide content lowered the toxicity. Sulfation of (1 .fwdarw. 5)-.alpha.-D-xylofuranan and -ribofuranan provided furanan-type heparinoids the anticoagulant activities of which were higher than those of the corresponding sulfated pyranan-type polysaccharides (1 .fwdarw. 4)-.beta.-D-xylopyranan and -ribopyranan. The highest activity (69.1 units/mg) was shown by sulfated (1 .fwdarw. 5)-.alpha.-D-xylofuranan. The dextran-type heparinoid having a sulfamide group showed a high anticoagulant activity also in vivo and high lipemia-clearing activity.