Synthesis and anti-HIV activity of triterpene conjugates of α-d-glucosamine

被引:0
作者
L. A. Baltina
R. M. Kondratenko
O. A. Plyasunova
L. A. Baltina
A. G. Pokrovskii
L. M. Khalilov
F. Z. Galin
G. A. Tolstikov
机构
[1] Russian Academy of Sciences,Institute of Organic Chemistry, Ufa Scientific Center
[2] Bashkir State Medical University,undefined
[3] State Scientific Center for Virology and Biotechnology “Vektor”,undefined
来源
Pharmaceutical Chemistry Journal | 2008年 / 42卷
关键词
Atomic Formula; Carbamoyl; Carbenoxolone; Glycyrrhizic Acid; Succinate Disodium;
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摘要
This report describes new triterpene conjugates of α-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-α-D-glucopyranos-2-yl)-carbamoyl]-phthaloyl-11-deoxyglycyrrhetic acid was found to have marked anti-HIV activity (the CD50 (50% cytotoxic concentration) was 150 µg/ml, the ID50 (50% effective concentration) was 1.5 µg/ml, and the index of selectivity (IS, IC50/ID50) was 100) andwas more active than GA in terms of IS (IS = 9.6).
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[1]   Synthesis of Triterpene Derivatives of D-Glucosamine - Modified Analogs of Glycyrrhizic Acid [J].
R. M. Kondratenko ;
S. R. Mustafina ;
L. A. Baltina ;
F. Z. Galin ;
G. A. Tolstikov .
Chemistry of Natural Compounds, 2005, 41 :7-10
[2]   Synthesis of triterpene derivatives of D-glucosamine - Modified analogs of glycyrrhizic acid [J].
Kondratenko, RM ;
Mustafina, SR ;
Baltina, LA ;
Galin, FZ ;
Tolstikov, GA .
CHEMISTRY OF NATURAL COMPOUNDS, 2005, 41 (01) :7-10
[3]   SYNTHESIS AND ANTI-HIV ACTIVITY OF TRITERPENE 3-O-GALACTOPYRANOSIDES, ANALOGS OF GLYCYRRHIZIC ACID [J].
Baltina, L. A., Jr. ;
Baltina, L. A. ;
Kondratenko, R. M. ;
Plyasunova, O. A. ;
Nepogodiev, S. A. ;
Field, R. A. .
CHEMISTRY OF NATURAL COMPOUNDS, 2010, 46 (04) :576-582
[4]   Synthesis and anti-HIV-1 activity of new conjugates of 18β- and 18α-glycyrrhizic acids with aspartic acid esters [J].
L. A. Baltina ;
E. S. Chistoedova ;
L. A. Baltina ;
R. M. Kondratenko ;
O. A. Plyasunova .
Chemistry of Natural Compounds, 2012, 48 :262-266
[5]   Synthesis and anti-HIV-1 activity of new conjugates of 18β- and 18α-glycyrrhizic acids with aspartic acid esters [J].
Baltina, L. A., Jr. ;
Chistoedova, E. S. ;
Baltina, L. A. ;
Kondratenko, R. M. ;
Plyasunova, O. A. .
CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (02) :262-266
[6]   Synthesis of new hetero- and carbocyclic aromatic amides of glycyrrhizic acid as potential anti-HIV agents [J].
R. M. Kondratenko ;
L. A. Baltina ;
L. A. Baltina. ;
O. A. Plyasunova ;
A. G. Pokrovskii ;
G. A. Tolstikov .
Pharmaceutical Chemistry Journal, 2009, 43 :383-388
[7]   Synthesis of new hetero- and carbocyclic aromatic amides of glycyrrhizic acid as potential anti-HIV agents [J].
Kondratenko, R. M. ;
Baltina, L. A. ;
Baltina, L. A., Jr. ;
Plyasunova, O. A. ;
Pokrovskii, A. G. ;
Tolstikov, G. A. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2009, 43 (07) :383-388
[8]   Synthesis and Antiviral Activity of Novel Glycyrrhizic Acid Conjugates with D-Amino Acid Esters [J].
Fayrushina, A. I. ;
Baltina, L. A., Jr. ;
Baltina, L. A. ;
Konovalova, N. I. ;
Petrova, P. A. ;
Eropkin, M. Yu. .
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2017, 43 (04) :456-462
[9]   Synthesis and antiviral activity of novel glycyrrhizic acid conjugates with D-amino acid esters [J].
A. I. Fayrushina ;
L. A. Baltina ;
L. A. Baltina ;
N. I. Konovalova ;
P. A. Petrova ;
M. Yu. Eropkin .
Russian Journal of Bioorganic Chemistry, 2017, 43 :456-462
[10]   Synthesis and Anti-HIV-1 Activity of Olean-9(11),12(13)-Dien-30-Oic Acid 3β-(2-O-β-D-Glucuronopyranosyl-β-D-Glucuronopyranoside) [J].
Baltina, L. A., Jr. ;
Stolyarova, O. V. ;
Kondratenko, R. M. ;
Gabbasov, T. M. ;
Baltina, L. A. ;
Plyasunova, O. A. ;
Il'ina, T. V. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (07) :439-443