SYNTHESIS AND ANTI-HIV ACTIVITY OF TRITERPENE CONJUGATES OF α-d-GLUCOSAMINE

This report describes new triterpene conjugates of alpha-D-glucosamine, i.e. modified glycyrrhizic acid (GA) analogs containing 18,19-dehydroglycyrrhetic acid 3-O-hemisuccinate and maleate and 11-deoxyglycyrrhetic acid 3-O-hemiphthalate fragments synthesized using N,N'-dicyclohexylcarbodiimide-N-hydroxybenzotriazole. 3-O-[3-(N-2-deoxy-alpha-D-glucopyranos-2-yl)-carbamoyl]-phthaloyl-11-deoxyglycyrrhetic acid was found to have marked anti-HIV activity (the CD50 (50% cytotoxic concentration) was 150 mu g/ml, the ID50 (50% effective concentration) was 1.5 mu g/ml, and the index of selectivity (IS, IC50/ID50) was 100) and was more active than GA in terms of IS (IS = 9.6).