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Improved syntheses of the Mglu₅ Antagonists MMPEP and MTEP using sonogashira cross-coupling


Mu, Boshuai; Mu, Linjing; Schibli, Roger; Ametamey, Simon M; Milicevic Sephton, Selena (2018). Improved syntheses of the Mglu₅ Antagonists MMPEP and MTEP using sonogashira cross-coupling. Pharmaceuticals, 11(1):E24.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > University Hospital Zurich > Clinic for Nuclear Medicine
Dewey Decimal Classification:610 Medicine & health
Uncontrolled Keywords:MMPEP; MTEP; Sonogashira cross-coupling; mGlu5 antagonist
Language:English
Date:20 February 2018
Deposited On:22 Aug 2018 14:58
Last Modified:31 Aug 2018 23:51
Publisher:MDPI Publishing
ISSN:1424-8247
OA Status:Gold
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.3390/ph11010024
PubMed ID:29461503

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