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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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
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author Mu, Boshuai
Mu, Linjing
Schibli, Roger
Ametamey, Simon M.
Milicevic Sephton, Selena
author_facet Mu, Boshuai
Mu, Linjing
Schibli, Roger
Ametamey, Simon M.
Milicevic Sephton, Selena
author_sort Mu, Boshuai
collection PubMed
description 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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spelling pubmed-58747202018-04-02 Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling Mu, Boshuai Mu, Linjing Schibli, Roger Ametamey, Simon M. Milicevic Sephton, Selena Pharmaceuticals (Basel) Article 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. MDPI 2018-02-20 /pmc/articles/PMC5874720/ /pubmed/29461503 http://dx.doi.org/10.3390/ph11010024 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Mu, Boshuai
Mu, Linjing
Schibli, Roger
Ametamey, Simon M.
Milicevic Sephton, Selena
Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling
title Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling
title_full Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling
title_fullStr Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling
title_full_unstemmed Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling
title_short Improved Syntheses of the mGlu(5) Antagonists MMPEP and MTEP Using Sonogashira Cross-Coupling
title_sort improved syntheses of the mglu(5) antagonists mmpep and mtep using sonogashira cross-coupling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5874720/
https://www.ncbi.nlm.nih.gov/pubmed/29461503
http://dx.doi.org/10.3390/ph11010024
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AT schibliroger improvedsynthesesofthemglu5antagonistsmmpepandmtepusingsonogashiracrosscoupling
AT ametameysimonm improvedsynthesesofthemglu5antagonistsmmpepandmtepusingsonogashiracrosscoupling
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