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

ABSTRACT: The Sonogashira cross-coupling, a key step in the syntheses of the mGlu? 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.

SUBMITTER: Mu B

PROVIDER: S-EPMC5874720 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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

Mu Boshuai B Mu Linjing L Schibli Roger R Ametamey Simon M SM Milicevic Sephton Selena S

Pharmaceuticals (Basel, Switzerland) 20180220 1

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. ...[more]

PMID: 29461503

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