H-1 NMR study of the conformation and absolute stereochemistry of two spirocyclic NK-1 antagonists

R. H.  Herbert; U.  Gerhard; R. J.  Mortishire-Smith; S. R.  Thomas; G.  Hollingworth

doi:10.1002/mrc.1604

H-1 NMR study of the conformation and absolute stereochemistry of two spirocyclic NK-1 antagonists

R. H. Herbert, U. Gerhard, R. J. Mortishire-Smith, S. R. Thomas, G. Hollingworth

School of Life and Medical Sciences

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

The binding affinities at the human NK-1 receptor of two spirocyclic compounds were found to be similar despite being epimeric at a key stereocentre. This unexpected result prompted a thorough investigation of the solution conformations of the two compounds. This revealed that a conformational switch in the tetrahydrofuran ring enabled the C-3-aryl group to be equatorial in both cases, leading to a similar juxtaposition of the aryl rings. Copyright (c) 2005 John Wiley & Sons, Ltd.

Original language	English
Pages (from-to)	658-661
Number of pages	4
Journal	Magnetic Resonance in Chemistry
Volume	43
Issue number	8
DOIs	https://doi.org/10.1002/mrc.1604
Publication status	Published - Aug 2005

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abstract = "The binding affinities at the human NK-1 receptor of two spirocyclic compounds were found to be similar despite being epimeric at a key stereocentre. This unexpected result prompted a thorough investigation of the solution conformations of the two compounds. This revealed that a conformational switch in the tetrahydrofuran ring enabled the C-3-aryl group to be equatorial in both cases, leading to a similar juxtaposition of the aryl rings. Copyright (c) 2005 John Wiley \& Sons, Ltd.",

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AU - Thomas, S. R.

AU - Hollingworth, G.

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N2 - The binding affinities at the human NK-1 receptor of two spirocyclic compounds were found to be similar despite being epimeric at a key stereocentre. This unexpected result prompted a thorough investigation of the solution conformations of the two compounds. This revealed that a conformational switch in the tetrahydrofuran ring enabled the C-3-aryl group to be equatorial in both cases, leading to a similar juxtaposition of the aryl rings. Copyright (c) 2005 John Wiley & Sons, Ltd.

AB - The binding affinities at the human NK-1 receptor of two spirocyclic compounds were found to be similar despite being epimeric at a key stereocentre. This unexpected result prompted a thorough investigation of the solution conformations of the two compounds. This revealed that a conformational switch in the tetrahydrofuran ring enabled the C-3-aryl group to be equatorial in both cases, leading to a similar juxtaposition of the aryl rings. Copyright (c) 2005 John Wiley & Sons, Ltd.

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DO - 10.1002/mrc.1604

M3 - Article

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SP - 658

EP - 661

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

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ER -

H-1 NMR study of the conformation and absolute stereochemistry of two spirocyclic NK-1 antagonists

Abstract

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