Beilstein J. Org. Chem.2020,16, 798–808, doi:10.3762/bjoc.16.73
conditions. Furthermore, the reasons for the appearance of byproducts were elucidated. Crystallographic data of a selected piperazinyl amide is reported.
Keywords: 18β-glycyrrhetinic acid; piperazinyl amides; synthesis; Introduction
Glycyrrhizin was the major bioactive component in Glycyrrhiza uralensis
fisch root. 18β-glycyrrhetinic acid (1, Figure 1) was then obtained by hydrolysis of glycyrrhizin. 18β-glycyrrhetinic acid and its derivatives have been extensively investigated in medicinal chemistry for their various biological activities, including anti-inflammatory [1], antiulcer [2], antioxidative
PDF
Graphical Abstract
Figure 1:
Chemical structure of 18β-glycyrrhetinic acid and known derivatives.
Beilstein J. Org. Chem.2012,8, 705–711, doi:10.3762/bjoc.8.79
need for new antiviral compounds. Starting from the natural, antivirally active compound glycyrrhizin, spacer-bridged derivatives were generated with improved antiviral activity against the influenza A virus infection. Simplified analogues of the triterpene saponin glycyrrhizin containing 1-thio-β-D
. The deprotected compounds containing these carboxylic acid appendices mimic the glycon part of glycyrrhizin as well as the hemisuccinate derivative of glycyrrhetinic acid, carbenoxolone. Antiviral activities of the compounds were determined in a biological test based on influenza A virus-infected
cells, wherein the 3-(2-thioethyl)-N-acetylamino- and 3-(2-thioethyl)-thio-linked glucuronide derivatives were effective inhibitors with IC50 values as low as 54 µM.
Keywords: antiviral activity; carbenoxolone; glycyrrhizin; influenza A virus; thioglycoside; triterpene; Introduction
The triterpene
PDF
Graphical Abstract
Figure 1:
Structure of glycyrrhizin (GL), carbenoxolone (CBX), and spacer analogues.