SYNTHESIS AND ANTI-HIV ACTIVITY OF TRITERPENE 3-O-GALACTOPYRANOSIDES, ANALOGS OF GLYCYRRHIZIC ACID

被引：3

作者：

Baltina, L. A., Jr. ^{[1
,2
]}

Baltina, L. A. ^{[1
,2
]}

Kondratenko, R. M. ^{[1
]}

Plyasunova, O. A. ^{[3
]}

Nepogodiev, S. A. ^{[4
]}

Field, R. A. ^{[4
]}

机构：

[1] Bashkir State Med Univ, Ufa 450000, Russia

[2] Russian Acad Sci, Inst Organ Chem, Ufa Sci Ctr, Ufa 450054, Russia

[3] State Sci Ctr Virusol & Biotechnol Vector, Koltsov 633159, Novosibirsk Obl, Russia

[4] Univ E England, Ctr Carbohydrate Chem, Sch Chem & Pharmaceut Sci, Norwich NR4 7TJ, Norfolk, England

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2010年 / 46卷 / 04期

基金：

英国生物技术与生命科学研究理事会;

关键词：

triterpene glycosides; glycyrrhizicacid; glycyrrhetic acid; glycosylation; iodine monobromide; anti-HIV-1; activity; HEMOLYTIC PROPERTIES; GLYCOSIDES; DIGLYCOSIDES; IODINE;

D O I：

10.1007/s10600-010-9679-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18 beta-glycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide as the glycosyl donor, I-Br promoter, and 4-angstrom molecular sieves was developed. The method could produce primarily 3-O-alpha-D- or beta-D-galactopyranosides depending on the reaction conditions. The 3-O-alpha-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. beta-D-Galactopyranoside of GLA was more cytotoxic for MT-4 cells and exhibited weak anti-HIV-1 activity.

引用

页码：576 / 582

页数：7

共 17 条

[1]

[Anonymous], 1995, SAPONINS

[2]

BALTINA LA, 2007, THESIS PERM

[3]

Ford, 1972, CHEM COMPANION

[4]

Kartha KPR, 2001, SYNLETT, P260

[5]

Kartha KPR, 1997, TETRAHEDRON LETT, V38, P8233

[6]

Kondratenko R.M., 2001, Khim.-Farm. Zh, V35, P39

[7]

MIKHAILOVA LR, 2009, BIOORG KHIM, V35, P686

[8]

MUSTAFINA SR, 2001, THESIS UFA

[9]

PLYASUNOVA OA, 1992, VOP VIRUSOL+, P235

[10] Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4-induced hepatic injury in vitro [J].

Saito, S ;

Nagase, S ;

Kawase, M ;

Nagamura, Y .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (7-8) :557-574

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