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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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
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Language:English
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Antiviral activity
Cytotoxicity
Human immunodeficiency virus
triterpenes
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container_issue 2
container_start_page 64
container_title Pharmaceutical chemistry journal
container_volume 42
creator Baltina, L A
Kondratenko, R M
Plyasunova, O A
Pokrovskii, A G
Khalilov, L M
Galin, F Z
Tolstikov, G A
description 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).
doi_str_mv 10.1007/s11094-008-0061-6
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subjects Antiviral activity
Cytotoxicity
Human immunodeficiency virus
triterpenes
title Synthesis and anti-HIV activity of triterpene conjugates of Delta a-d-glucosamine
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