Chemists have discovered a way to use visible light to synthesize a class of compounds particularly well suited for use in pharmaceuticals. The class of compounds, called azetidines, had been previously identified as a good candidate to build therapeutic drugs, but the compounds are difficult to produce in chemical reactions.
Now, a team has developed a method to produce a specific class of azetidines called monocyclic azetidines using visible light and a photocatalyst.
"The ring systems can break down in the body after a patient has ingested a therapeutic drug. Because the compound can be metabolized by the human body, what you give initially to a patient may not necessarily be what you would find in the body after the patient has taken it, and that is a problem." In the reaction, the researchers used two classes of compounds called acyclic imines and alkenes, which are highly desirable as starting materials because they can be easily varied to produce different products, Wearing says. However, when you use light to excite the imine, the acyclic imine decays from the excited state before it can undergo the cycloaddition, Schindler says.
Her lab ran a computational analysis that found using specific classes of the imines and alkenes starting materials would facilitate a better match in energy between those starting materials, which lowered the barrier for reaction. They also analyzed what factors led to high yields of azetidines. "The synthesis of these azetidine compounds are examples to demonstrate that this synthetic methodology can be applied to make complicated molecules and medicine-like molecules," Yeh said.
Pharmaceuticals Allergy Gene Therapy Chemistry Inorganic Chemistry Optics Organic Chemistry
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