Chemists synthesize a better building block for drugs


Chemists have overcome a major hurdle in synthesizing a more stable form of heterocycles. Heterocycles are a family of organic compounds that are a common component of most modern drugs.

This research, which could expand the toolkit available to drug developers to improve the safety profile of drugs and reduce side effects, was published in 2012. Science By organic chemists from the University of British Columbia (UBC), the Massachusetts Institute of Technology (MIT), and the University of Michigan.

“Azetidines are a particularly useful, stable form of heterocycle, but synthesizing them has been incredibly challenging,” says Dr. Corinna Schindler, Canada Research Chair in Synthetic Solutions for Bioactive Compounds at UBC and senior author of the paper.

Heterocycles play a major role in the design of modern drug families – including cancer drugs and antibiotics. Some reviews suggest that 85 percent of all biologically active chemical units contain heterocycles.

But many of the heterocycles currently used in drug design oxidize under physiological conditions. This can lead to off-target effects and challenges with the safety profile of drugs.

Azetidins – organic compounds containing three carbon atoms and one nitrogen atom, and which are liquid at room temperature – are considered metabolically robust and do not undergo oxidation reactions under physiological conditions.

“This is something that synthetic organic chemists have been trying to achieve for a long time, and we hope this will help researchers develop new synthetic modifications of azetidines with more useful chemical and medical functions,” says Dr. Schindler, whose lab conducted the research in collaboration with graduate student Emily Wareing at the University of Michigan and with Dr. Heather Kulik’s lab at the Massachusetts Institute of Technology.

The team used light-driven reactions and a computational approach to this problem and for the first time was able to productively incorporate compounds called imines into the reaction to create new azetidines.


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