Synthesis and anti-HIV activity of triterpene 3-O-galactopyranosides, analogs of glycyrrhizic acid
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A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18βglycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-a-Dgalactopyranosyl bromide as the glycosyl donor, I–Br promoter, and 4-Å molecular sieves was developed. The method could produce primarily 3-O-α-D- or β-D-galactopyranosides depending on the reaction conditions. The 3-O-α-D-galactopyranoside of GLA exhibited an index of selectivity (IS) 2.9 times greater than that of GA for inhibition of accumulation of virus-specific protein p24 of HIV-1. β-D-Galactopyranoside of GLA was more cytotoxic for MT-4 cells and exhibited weak anti-HIV-1 activity.
Keywordstriterpeneglycosides,glycyrrhizicacid,glycyrrhetic acid glycosylation iodine monobromide anti-HIV-1 activity
The work was financed by the Royal Society of Great Britain (Project gt/fSU17p), the Federal Agency for Science and Innovation (State Contract 02.434.11.7060), and the RFBR (08-03-13514ofi-ts).
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