Design and synthesis of novel goniothalamin analogs

CHED 294

Allissa A. Dillman and Mark F. Mechelke, mfmechelke@stcloudstate.edu. Department of Chemistry, St. Cloud State University, 358 Wick Science Building, 720 Fourth Avenue South, St. Cloud, MN 56301
Every two minutes a woman in the United States is diagnosed with breast cancer. One method to identify potential chemotherapeutic agents has been the mass screening of natural products for cytotoxicity. A compound discovered in this manner was goniothalamin. Goniothalamin was isolated from the stem bark of the plant goniothalamus sesuipedalis and exhibits cell specific anticancer activity against breast cancer cell lines. Goniothalamin has been extensively studied, and a large number of analogues have been prepared in an attempt to determine the structural features necessary for bioactivity. These structure/activity relationship studies have focused primarily on the manipulation of goniothalamin's styryl substituent. The focus of this research is on the lactone core of goniothalamin. Analogues have been prepared that replace the lactone ring with a lactam. It is anticipated that alteration of the lactam nitrogen substituent will potentially lead to analogues that have better bioavailability and reactivity than the natural product.