Title: Synthesis of triterpenoid triazine derivatives from allobetulone and betulonic acid with biological activities
Authors: Dinh Ngoc, Thuc ×
Moons, Nico
Kim, Youngju
De Borggraeve, Wim
Mashentseva, Anastassiya
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
Dehaen, Wim #
Issue Date: Jul-2014
Publisher: Pergamon
Series Title: Bioorganic & Medicinal Chemistry vol:22 issue:13 pages:3292-3300
Article number: 10.1016/j.bmc.2014.04.061
Abstract: The synthetic transformation and modification of natural products with the aim to improve the biological properties is an area of current interest. The triterpenoids betulin and betulinic acid are very abundant in nature and now are commercially available. In our study, starting from betulin and betulinic acid, we obtained allobetulone and betulonic acid in a few synthetic steps. The ketone function at the A-ring was used as the starting point for the synthesis of a series of 1,2,4-triazine-fused triterpenoids. The alkylation and Liebeskind-Srogl coupling were used for further substitution of 1,2,4-triazines, and the intramolecular hetero Diels-Alder reaction leads to interesting fused thienopyridine derivatives. All new compounds were tested for their cytostatic activities against murine leukemia L1210, human cervix carcinoma HeLa and human lymphoblast CEM tumor cells. The results show that some triterpenoid triazine betulonic acid derivatives have a promising cytostatic activity in vitro and could be used as potential leads for the development of new type of anti-cancer agents. Several compounds were also endowed with anti-HCMV activity in the low micromolar range.
ISSN: 0968-0896
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
Molecular Design and Synthesis
× corresponding author
# (joint) last author

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