Journal
NEW JOURNAL OF CHEMISTRY
Volume 34, Issue 7, Pages 1450-1464Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b9nj00602h
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Funding
- National Natural Science Foundation of China [30672523, 90713037]
- Chinese Ministry of Education [706030, 20050316008]
- program for New Century Excellent Talents in University [NCET-05-0495]
- National Office for Research and Technology [NI-61336, NK-68578, CK-77712]
- NORT Hungary [CHN-25/05]
- Program for Chinese-Hungarian Scientific and Technological Cooperation (China) [CHN-7/2006]
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Propargyl esters of the C-28 carboxylic acids of pentacyclic triterpenes (oleanolic, ursolic, and maslinic acids) were coupled with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide as well as N-(omega-azido-[C-2, C-6, and C-11]alkanoyl)-beta-D-glucopyranosylamines under conditions of copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) to give tethered D-glucose-triterpene heteroconjugates. The O-acetyl protecting groups were removed by base-catalyzed hydrolysis. N-(omega-Azido-[C-2, C-6, C-11, and C-16]alkanoyl)-beta-D-glucopyranosylamines were also tethered by 1,7-octadiyne under CuAAC conditions to furnish D-glucose homoconjugates. O-Deacetylation was carried out by the Zemplen protocol. The new compounds were assayed against rabbit muscle glycogen phosphorylase (RMGP) a or b enzymes. Some of the heteroconjugates inhibited the enzyme in the low micromolar range (IC(50) values 40-70 mu M), while the homoconjugates proved inefficient as inhibitors.
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