A new way to prepare fluorinated pharmaceuticals

August 13, 2009 by Anne Trafton

(PhysOrg.com) -- A team of MIT chemists has devised a new way to add fluorine to a variety of compounds used in many drugs and agricultural chemicals, an advance that could offer more flexibility and potential cost-savings in designing new drugs.

Drug developers commonly add fluorine atoms to drugs, such as the cholesterol-lowering rosuvastatin, to keep the body from breaking them down too quickly. Many of these drugs contain aromatic rings — a type of six-carbon ring — and attaching a fluorine atom to the rings can be a difficult, expensive process.

"It's hard to add fluorine at a late stage, once you have a complete molecule already put together, because traditional methods can be quite harsh with respect to temperature or other factors," says Stephen L. Buchwald, the Camille Dreyfus Professor of Chemistry at MIT.

In their new technique, Buchwald and his colleagues used a palladium catalyst to attach a fluorine atom to aromatic compounds. The technique could be used in the design and testing of new drugs, or to create new imaging agents for positron (PET) scanning.

Donald Watson, a former postdoctoral associate in Buchwald's lab, now an assistant professor of chemistry at the University of Delaware, is lead author of a paper describing the new synthesis in the Aug. 13 early online edition of Science.

During the new process, the catalyst removes a group of atoms called a triflate attached to the aromatic compound, then replaces it with a fluorine atom taken from a simple salt, such as fluoride. This marks the first time chemists have replaced a triflate attached to an aromatic ring with a fluorine atom in one catalytic reaction.

"Many people believed it would not be possible to do this," says Buchwald.

"While the method is probably not currently efficient enough to be used in manufacturing, we are working to speed up the reaction, increase its efficiency and make it more environmentally and user-friendly," says Buchwald. "We ultimately hope to make it general enough to be useful for manufacturing."

Source: Massachusetts Institute of Technology (news : web)

Explore further: UCR chemists prepare molecules that accelerate chemical reactions for manufacturing drugs

Related Stories

From rare bugs to test tube drugs

December 23, 2008

(PhysOrg.com) -- Scientists at the University of St Andrews have created exotic biological compounds in a test tube by uncovering some of Nature's chemical secrets.

Recommended for you

Brazilian wasp venom kills cancer cells by opening them up

September 1, 2015

The social wasp Polybia paulista protects itself against predators by producing venom known to contain a powerful cancer-fighting ingredient. A Biophysical Journal study published September 1 reveals exactly how the venom's ...

Water heals a bioplastic

September 1, 2015

A drop of water self-heals a multiphase polymer derived from the genetic code of squid ring teeth, which may someday extend the life of medical implants, fiber-optic cables and other hard to repair in place objects, according ...

Naturally-occurring protein enables slower-melting ice cream

August 31, 2015

(Phys.org)—Scientists have developed a slower-melting ice cream—consider the advantages the next time a hot summer day turns your child's cone with its dream-like mound of orange, vanilla and lemon swirls with chocolate ...

3 comments

Adjust slider to filter visible comments by rank

Display comments: newest first

E_L_Earnhardt
5 / 5 (1) Aug 14, 2009
Fluqrine is on the "poisen" list!
deatopmg
1 / 5 (1) Aug 14, 2009
@ELE; so is water if you drink too much or if you try to breathe it. Triflic acid isn't very kindly if ingested either.
So what, it's chemistry.
Nik_2213
not rated yet Aug 26, 2009
ELE, next time you reach for your salt-cellar, please remember that sodium is a very nasty metal, and chlorine is a CBW poison gas.

Please sign in to add a comment. Registration is free, and takes less than a minute. Read more

Click here to reset your password.
Sign in to get notified via email when new comments are made.