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

journal contribution
posted on 2023-06-08, 06:46 authored by Peter B Hitchcock, Konstantinos Papadopoulos, Douglas W Young
The activated ß-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.

History

Publication status

  • Published

Journal

Organic and Biomolecular Chemistry

ISSN

1477-0520

Publisher

RSC Publishing

Issue

15

Volume

1

Page range

2670-2681

Pages

12.0

Department affiliated with

  • Chemistry Publications

Notes

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.

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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