Factors influencing the cytotoxicity of a-methylene-γ-hydroxy esters against pancreatic cancer, and the development of a chiral route to AMGBLs

Matthew A Helppi, Purdue University


Reported herein is the synthesis of a variety of Michael acceptors related to α-methylene-γ-butyrolactones (AMGBLs) and their evaluation as anti-pancreatic cancer agents. The study revealed that, the Michael acceptor capabilities of a number of AMGBL derivatives is not the major factor that affects biological activity but the number of carbons and the ability to lactonize are crucially important. It was also shown that a number of α-methylene-γ-hydroxy esters are equally, or even more, active than the corresponding AMGBLs. Additionally, a new route to synthesize chiral AMGBLs via dynamic kinetic resolution using a chiral catalyst is described.




Ramchandran, Purdue University.

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