Synthesis of Lupane-Type Saponins Containing an Unusual alpha-D-Idopyranoside Fragment as Potent Cytotoxic Agents

0433374 - ÚEB 2015 RIV DE eng J - Journal Article
Cmoch, P. - Korda, A. - Rárová, Lucie - Oklešťková, Jana - Strnad, Miroslav - Gwardiak, K. - Karczewski, R. - Pakulski, Z.
Synthesis of Lupane-Type Saponins Containing an Unusual alpha-D-Idopyranoside Fragment as Potent Cytotoxic Agents.
European Journal of Organic Chemistry. JUL 2014, č. 19 (2014), s. 4089-4098. ISSN 1434-193X. E-ISSN 1099-0690
R&D Projects: GA MŠMT(CZ) LO1204; GA ČR GA14-19590S
Institutional support: RVO:61389030
Keywords : Carbohydrates * Glycoconjugates * Glycosylation
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 3.065, year: 2014

A practical method for the preparation of benzoyl protected allyl and benzyl alpha-D-idopyranosides, and D-idopyranosyl trichloroacetimidate, from 1,2,3,4,6-penta-O-acetyl-alpha-D-idopyranose, is described. All derivatives can be prepared on a multigram scale and require only simple chromatographic purification. A concise synthesis of lupane triterpenes bearing an unusual D-idopyranoside fragment is described. All new compounds were evaluated in vitro for their cytotoxic activities. Novel saponins exhibited interesting cytotoxic activity in the micromolar range against human cancer cell lines including T-lymphoblastic leukemia CEM, breast adenocarcinoma MCF7, and cervical carcinoma HeLa, but also against normal human fibroblasts BJ.
Permanent Link: http://hdl.handle.net/11104/0237582