Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling

The Sonogashira cross-coupling, a key step in the syntheses of the mGlu(5) 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 synth...

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Detalles Bibliográficos
Autores principales: Mu, Boshuai, Mu, Linjing, Schibli, Roger, Ametamey, Simon M., Milicevic Sephton, Selena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5874720/
https://www.ncbi.nlm.nih.gov/pubmed/29461503
http://dx.doi.org/10.3390/ph11010024
Descripción
Sumario:The Sonogashira cross-coupling, a key step in the syntheses of the mGlu(5) 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.

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