CHED 820 |
| Jeremy C. Perry, Jesse Miller, and Edward J. Brush. Department of Chemical Sciences, Bridgewater State College, Park Avenue, Bridgewater, MA 02325 |
| Glyoxalase I (GxI) is a glutathione-dependent detoxification enzyme used by all living organisms, that may play a role in the regulation of tumor cell growth. Our research involves the synthesis of oxindole derivatives as potential GxI inhibitors. Inhibition of GxI may result in an increased concentration of intracellular methylglyoxal that may induce apoptosis and destroy the tumor cells. The current synthesis of 3-methyleneoxindole (MOI) from indoleacetic acid (IAA) and N-bromosuccinimide is not environmentally friendly. We have investigated a variety of methods for the one-pot synthesis of MOI from IAA, and found that biphasic reaction conditions utilizing oxidizing agents to produce electrophilic bromine from bromide ion are effective in the synthesis of 3-bromooxindole acetic acid and MOI. The amount of waste produced is greatly reduced and the reaction proceeds with high atom economy. This research was supported by the Research Corporation, NCUR/Lancy initiative, and Adrian Tinsley Program. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |