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

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

Access to Document

10.1002/mrc.1604

Cite this

@article{01da1a3daffb4ddaab374662c26b6618,

title = "H-1 NMR study of the conformation and absolute stereochemistry of two spirocyclic NK-1 antagonists",

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.",

author = "Herbert, \{R. H.\} and U. Gerhard and Mortishire-Smith, \{R. J.\} and Thomas, \{S. R.\} and G. Hollingworth",

year = "2005",

month = aug,

doi = "10.1002/mrc.1604",

language = "English",

volume = "43",

pages = "658--661",

journal = "Magnetic Resonance in Chemistry",

issn = "0749-1581",

publisher = "Wiley",

number = "8",

}

TY - JOUR

T1 - H-1 NMR study of the conformation and absolute stereochemistry of two spirocyclic NK-1 antagonists

AU - Herbert, R. H.

AU - Gerhard, U.

AU - Mortishire-Smith, R. J.

AU - Thomas, S. R.

AU - Hollingworth, G.

PY - 2005/8

Y1 - 2005/8

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.

U2 - 10.1002/mrc.1604

DO - 10.1002/mrc.1604

M3 - Article

SN - 0749-1581

VL - 43

SP - 658

EP - 661

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

IS - 8

ER -

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

Abstract

Access to Document

Fingerprint

Cite this