Improved Syntheses of the Mglu₅ Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling.
Published version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Mu, Boshuai
Mu, Linjing
Schibli, Roger
Ametamey, Simon M
Milicevic Sephton, Selena https://orcid.org/0000-0002-1105-6726
Abstract
The Sonogashira cross-coupling, a key step in the syntheses of the mGlu₅ antagonists MMPEP and MTEP, provided an improved three-step method for the preparation of MMPEP in 62% overall yield. Using Spartan molecular modeling kit an explanation for the failure to employ analogues method in the synthesis of MTEP was sought. The DFT calculations indicated that meaningful isolated yields were obtained when the HOMO energy of the aryl halide was lower than the HOMO energy of the respective alkyne.
Description
Keywords
MMPEP, MTEP, Sonogashira cross-coupling, mGlu5 antagonist
Journal Title
Pharmaceuticals (Basel)
Conference Name
Journal ISSN
1424-8247
1424-8247
1424-8247
Volume Title
11
Publisher
MDPI AG