Improved Syntheses of the Mglu₅ Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling.

Boshuai MuLinjing MuRoger SchibliSimon M AmetameySelena Milicevic Sephton

Published in: Pharmaceuticals (Basel, Switzerland) (2018)

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.

Keyphrases

density functional theory
molecular docking
molecular dynamics
molecular dynamics simulations
mass spectrometry
solar cells