The reaction, designed by chemistry Professor Mark Lautens and graduate student Eric Fang, simplifies the creation of the basic molecular framework found in many natural products and popular pharmaceuticals like some cholesterol-lowering drugs. Until now, synthesizing this framework - an indole - was inefficient, requiring six to 10 steps and often producing toxic by-products. "This new method only takes three steps and results in less waste," says Lautens, the NSERC-Merck Frosst Industrial Research Chair in New Medicinal Agents via Catalytic Reactions and AstraZeneca Professor of Organic Synthesis.
Indoles are ring structures containing carbon and nitrogen. In the process, the researchers used a metallic element as a catalyst to form two chemical bonds and create a diverse range of indole-containing compounds. These compounds could then be used to make drugs now on the market or form the basis of new therapeutic drugs.
Lautens says this new molecular-level technique could equal big savings and less environmental impact. "In order to make a hundred kilograms of these best-selling drugs, there are often hundreds of litres of solvent used, not to mention the many purification processes involved. Not only are you speeding up the process, you're also reducing waste and energy used in manufacturing."
A provisional patent was filed by U of T's Innovations Foundation in March. The research was funded by the Natural Sciences and Engineering Research Council of Canada.
CONTACT: Professor Mark Lautens, U of T Department of Chemistry, 416-978-6083, mlautens@chem.utoronto.ca, or Karen Kelly, U of T Public Affairs, 416-978-6974, k.kelly@utoronto.ca
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