Issue 12, 2015
From the journal:

MedChemComm

Novel N-thiazolyl piperazine-1-carboxamide CCR2 antagonists – investigation of an unexpected reaction with glutathione†

J. G. Cumming,a   P. A. MacFaulb  and  A. G. Leach ORCID logo *c  

* Corresponding authors

a F. Hoffmann-La Roche, Grenzacherstrasse, CH-4070 Basel, Switzerland

b Redx Pharma, 3S30, BioHub, Alderley Park, Macclesfield, Cheshire, UK

c School of Pharmacy and Biomolecular Sciences, James Parsons Building, Byrom Street, Liverpool, UK
E-mail: a.g.leach@ljmu.ac.uk

Abstract

A series of CCR2 antagonists containing halothiazoles were found to undergo an unexpected reaction with glutathione. Experiments revealed the structure–reactivity relationship and calculations suggest that competition between two reactions of a tautomer of the reactant (deprotonation and nucleophilic addition) governs the rate of this reaction.

Graphical abstract: Novel N-thiazolyl piperazine-1-carboxamide CCR2 antagonists – investigation of an unexpected reaction with glutathione

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C5MD00362H
Article type
Concise Article
Submitted
25 Aug 2015
Accepted
08 Oct 2015
First published
19 Oct 2015

Med. Chem. Commun., 2015,6, 2140-2145

Author version available

Download author version (PDF)

Permissions

Request permissions

Novel N-thiazolyl piperazine-1-carboxamide CCR2 antagonists – investigation of an unexpected reaction with glutathione

J. G. Cumming, P. A. MacFaul and A. G. Leach, Med. Chem. Commun., 2015, 6, 2140 DOI: 10.1039/C5MD00362H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements