ORGN 403 |
| Four new uprolides (I-L) were synthesized from eupalmerin acetate, in no more than three steps, via a regioselective phenylselenylether intermediate that was further submitted to oxidative work-up conditions to generate the alkene moiety. These compounds possess a 3,7-oxa-bridge in its macrocyclic structure previously observed in uprolides F diacetate and G acetate, two cembranolides isolated from the Caribbean gorgonian octocoral Eunicea mammosa. The chemical structures of uprolides I-L were elucidated using 1D and 2D NMR experiments. Since uprolides F and G, were marginally evaluated against several cancer cell lines displaying potent cytotoxic activity against leukemic, colon and breast cancer cells (IC50 = 0.6-7μg/mL), we expect that uprolides I-L display enhanced cytotoxicity against human cancer cell lines. Therefore, their biological evaluation is currently under investigation.
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New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Sci-Mix
Division of Organic Chemistry |
