1257409-37-2

Upstream product

• 1207976-43-9 (3β,18β,20β)-3-amino-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester 
• 1257409-36-1 methyl (1-O-(2-iodoethyl)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate 
• 1392101-40-4 methyl (1-O-(2-bromoethyl)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate 
• 68354-87-0 1-Thio-1-desoxy-(2,3,4-tri-O-acetyl-β-D-glucuronsaeuremethylester) 
• 314079-40-8 methyl (2,3,4-tri-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranosyl)uronate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Downstream Products

• 1257409-39-4 (3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester 
• 1257409-41-8 (3S,18R,20S)-3-{N-(4-methoxy-1,4-dioxobutyl)-N-[2-S-(methyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyluronate)ethyl]amino}-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester 

Relevant academic research and scientific papers

Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin

The influenza virus infection remains a significant threat to public health and the increase of antiviral resistance to available drugs generates an urgent need for new antiviral compounds. Starting from the natural, antivirally active compound glycyrrhizin, spacerbridged 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-glucuronic acid residues have been prepared in good yields by alkylation of 3-amino and 3-thio derivatives of glycyrrhetinic acid with a 2-iodoethyl 1-thio-β-D-glucopyranosiduronate derivative. The spacer-connected 3-amino derivatives were further transformed into N-acetylated and N-succinylated derivatives. 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.

ANTIVIRAL TRITERPENE DERIVATIVES

The present invention encompasses novel triterpene compounds of general Formula (I) wherein RN1, RN2, R11a, R11b, R4, R17, R19 and R20 are defined as in claim 1, which exhibit an antiviral effect and are therefore suitable for the treatment of diseases related thereto and the use thereof for preparing a medicament having the above-mentioned properties.