Synthesis and characterization of amino phenyl propane derivatives as monoamine transport inhibitors

CHED 274

Bruce J. Heyen, bruceh@tabor.edu1, Scott Adrian, scottadr@tabor.edu1, and Kandatege Wimalasena, kandatege.wimalasena@wichita.edu2. (1) Department of Chemistry, Tabor College, 400 S. Jefferson, Hillsboro, KS 67063, (2) Department of Chemistry, Wichita State University, Wichita, KS 67260
A series of 4'- 3'- and 2'-iodo-3-amino-2-phenylpropene derivatives are easily synthesized starting with the Wittig synthesis of the corresponding iodo-acetophenone to produce an alpha-methylstyrene derivative. Next, the allylic position of the alkene is brominated with NBS. The Gabriel synthesis followed by hydrazinolysis produces the desired 3-amino-2-phenylpropene (APP) product. The 4'-I derivatives have been previously shown to inhibit vesicular monoamine transport. Since the 4-I-APP derivative is a reversible competitive inhibitors with similar affinities of most pharmacologically active monoamines, these derivatives are useful agents for the study of dopamine transport into storage vesicles.
 

Undergraduate Research Poster Session
2:30 PM-4:30 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Chemical Education

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007