Baylis Hillman (BH) reaction is important for C-C bond forming reactions in organic synthesis. Allyl alcohols can be synthesized readily by this reaction and these alcohols undergo nucleophilic rearrangement to provide wide range of useful synthons for organic and medicinal chemistry. We are interested in the development of new molecules based on BH reaction and we have initiated this project to explore novel functionalized allyl esters derived from BH reaction as potential anticancer agents. We synthesized several carboxylic acids derived analogs of bromomethyl phenyl acrylate obtained from BH reaction. The allyl ester was further dihydroxylated using OsO4. The synthesized molecules have been evaluated against several cancer cells including triple negative breast cancer cell line MDA-MB-231, and pancreatic cancer cell line MIAPaCa-2. These studies have indicated that several of the synthesized compounds show good cytotoxicity with EC50 values in the range of 3-73μM. Interestingly, the removal of electrophilic double bond in both compounds 2 and 4 reduced the biological activity.
University Honors Capstone Project Paper and Poster and Undergraduate Research Opportunities Program (UROP), University of Minnesota Duluth, 2017. Yishu Zhang authored paper and poster; Jake Gibbons, Skylar Hubbard, Tanner Schumacher, and Zachary Gardner authored poster.
Zhang, Yishu; Gibbons, Jake; Hubbard, Skylar; Schumacher, Tanner; Gardner, Zachary.
Synthesis and Biological Evaluation of Simple Baylis-Hillman Carboxylic Acid Esters as Potential Anticancer Agents.
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