ORGN 510 |
| Zachary J. O'Brien1, Saeed Attar1, and Alejandro Calderon-Urrea2. (1) Department of Chemistry, California State University, Fresno, 2555 E. San Ramon Ave., M/S SB-70, Fresno, CA 93740, (2) Department of Biology, California State University, Fresno, 2555 E. San Ramon Ave., M/S SB-73, Fresno, CA 93740 |
| Two families of ferrocenyl chalcones were synthesized according to Schemes 1 and 2 below. The compounds were characterized by 1H NMR, IR and UV-Vis spectroscopy. The compounds were administered to C. elegans nematodes in three different concentrations (1, 10, and 100 μM) to ascertain minimum levels of toxicity. The solutions were 1% DMSO and 99% (v/v) liquid medium. DMSO alone in concentrations greater than 1% was lethal to the nematodes. Each nematode was placed in 50 μL of the test solution and 10 duplicates were run for each compound. The active compounds were then duplicated 96 times for a better statistical cross-section. Results point to the existence of some biological activity, especially for 1-(4’-fluorophenyl)-3-ferrocenyl-2-propen-1-one (3, R=4-F). After fourteen days of exposure to this compound, 78% of the nematodes were killed. Of the surviving 22%, all but one had reproduced. There seems to be a correlation between biological activity and the position of the ferrocene moiety and the presence of electron-withdrawing groups on the phenyl ring. Further investigations into the structure-activity relationships in this series of compounds are underway.
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
