Synthesis and anti-HIV activity of triterpene conjugates of Delta a-d-glucosamine

This report describes new triterpene conjugates of Delta *a-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'-dicyclohexylcarbodiimi...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2008-02, Vol.42 (2), p.64-67
Main Authors: Baltina, L A, Kondratenko, R M, Plyasunova, O A, Pokrovskii, A G, Khalilov, L M, Galin, F Z, Tolstikov, G A
Format: Article
Language:English
Subjects:
Antiviral activity
Cytotoxicity
Human immunodeficiency virus
triterpenes
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Summary:This report describes new triterpene conjugates of Delta *a-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- Delta *a-D-glucopyranos-2-yl)-carbamoyl]-phthaloyl-11 -deoxyglycyrrhetic acid was found to have marked anti-HIV activity (the CD50 (50% cytotoxic concentration) was 150 ?g/ml, the ID50 (50% effective concentration) was 1.5 ?g/ml, and the index of selectivity (IS, IC50/ID50) was 100) andwas more active than GA in terms of IS (IS = 9.6).
ISSN:0091-150X
DOI:10.1007/s11094-008-0061-6