ORGN 501 |
| Udayan Das1, Heather Strachan2, Kelley Moremen2, and Aloysius Siriwardena1. (1) Department of Chemistry and Biochemistry, University of Mississippi, University, MS 38677, (2) The Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30606 |
| A series of novel heterocyclic analogs have been obtained by efficient chemical routes. These analogs resemble closely, natural indolizidine and pyrrolidizine alkaloids such as swainsonine which have attracted much interest due to their interesting and potent biological activities and inhibitory activity against glycosidases. The synthesis of a diverse range of polyhydroxylated heterocycles has been accomplished by the reaction of simple sugar precursors such as erythruronolactone and KCN, with various aminothiols or diamines. The reactions proceed efficiently, by a cascade mechanism, under very mild experimental conditions affording the target molecules in a single chemical step. After deprotection, the heterocyclic analogs were tested against human lysozomal and Golgi mannosidase II. Although the majority of derivatives displayed only low activity against either enzyme, one derivative was obtained which shows selective inhibition of the Golgi mannosidase II (ki=63 uM). This paper will outline the details of the synthesis of this novel series of polyhydroxylated heterocycles and describe their inhibitory activities. |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry |