beta-Lactams as versatile synthons for homochiral ibotenate analogues with potential for activity at glutamate receptors

Hitchcock, Peter B, Papadopoulos, Konstantinos and Young, Douglas W (2003) beta-Lactams as versatile synthons for homochiral ibotenate analogues with potential for activity at glutamate receptors. Organic and Biomolecular Chemistry, 1 (15). pp. 2670-2681. ISSN 1477-0520

Full text not available from this repository.

Abstract

The activated β-lactam aldehydes 37, 41 and 57 were synthesised. Aldehydes 37 and 57 proved to be more versatile substrates for our “ring switching” strategy to homochiral glutamate antagonists than the corresponding compounds in the pyroglutamate or 6-oxopipecolinate series had been. Substantial libraries of homochiral heteroaromatic glycine derivatives with potential for activity at specific glutamate receptor sub-types were prepared from these aldehydes. The aldehyde 41, containing an additional anion stabilising group, underwent a retro-aldol process under “ring switching” conditions.

Item Type: Article
Additional Information: DWY directed the work and is corresponding author. All authors were from Sussex. The work presents a general synthesis of a variety of homochiral amino acids designed to be ibotenate type glutamate antagonists which should therefore show promise as potential drugs for a variety of central nervous system disorders.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: EPrints Services
Date Deposited: 06 Feb 2012 20:33
Last Modified: 27 Mar 2012 15:45
URI: http://sro.sussex.ac.uk/id/eprint/26641
📧 Request an update