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Pharmaceuticals 2018, 11(1), 24; doi:10.3390/ph11010024

Improved Syntheses of the mGlu5 Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling

Center of Radiopharmaceutical Sciences of ETH, PSI and USZ, Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Vladimir-Prelog-Weg 4, 8093 Zurich, Switzerland
Department of Nuclear Medicine, University Hospital Zurich, Ramistrasse 101, 8003 Zurich, Switzerland
Molecular Imaging Chemistry Laboratory, Wolfson Brain Imaging Centre, Department of Clinical Neurosciences, University of Cambridge, Box 65 Cambridge Biomedical Campus, Cambridge CB2 0QQ, UK
Author to whom correspondence should be addressed.
Received: 25 December 2017 / Revised: 10 February 2018 / Accepted: 12 February 2018 / Published: 20 February 2018
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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. View Full-Text
Keywords: Sonogashira cross-coupling; MMPEP; MTEP; mGlu5 antagonist Sonogashira cross-coupling; MMPEP; MTEP; mGlu5 antagonist

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Mu, B.; Mu, L.; Schibli, R.; Ametamey, S.M.; Milicevic Sephton, S. Improved Syntheses of the mGlu5 Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling. Pharmaceuticals 2018, 11, 24.

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