Approaches to spiro-heterocycles : novel scaffolds for drug discovery
Approaches to spiro-heterocycles : novel scaffolds for drug discovery
The tachykinins are a family of neuropeptides found in the body that have been implicated in a variety of deleterious conditions, ranging from asthma and pain transmission in migraine to ulcerative colitis and Crohn’s disease.
The work contained in this thesis is primarily concerned with the synthesis of potential tachykinin receptor antagonists based on a 1-oxa-8-azaspirol[4.5]decan-4-one skeleton. This has been achieved via the addition of ethoxyethyl-protected cyanohydrin 222 to a range of substituted piperidones with ensuing hydrolysis to the unsaturated hydroxyketone.
Ring-closure to form the spirocyclic furanone core was facilitated via an acid-mediated 5-endo-trig cyclisation. Reductive amination and deprotection of furanone 328 led to the isolation of amines 428 and 434 which served as ideal scaffolds for the synthesis of compound libraries.
University of Southampton
Hart, James Dudley
4ba81855-f72b-40ec-85a1-dbde49cedc43
2003
Hart, James Dudley
4ba81855-f72b-40ec-85a1-dbde49cedc43
Hart, James Dudley
(2003)
Approaches to spiro-heterocycles : novel scaffolds for drug discovery.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The tachykinins are a family of neuropeptides found in the body that have been implicated in a variety of deleterious conditions, ranging from asthma and pain transmission in migraine to ulcerative colitis and Crohn’s disease.
The work contained in this thesis is primarily concerned with the synthesis of potential tachykinin receptor antagonists based on a 1-oxa-8-azaspirol[4.5]decan-4-one skeleton. This has been achieved via the addition of ethoxyethyl-protected cyanohydrin 222 to a range of substituted piperidones with ensuing hydrolysis to the unsaturated hydroxyketone.
Ring-closure to form the spirocyclic furanone core was facilitated via an acid-mediated 5-endo-trig cyclisation. Reductive amination and deprotection of furanone 328 led to the isolation of amines 428 and 434 which served as ideal scaffolds for the synthesis of compound libraries.
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Published date: 2003
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Local EPrints ID: 465161
URI: http://eprints.soton.ac.uk/id/eprint/465161
PURE UUID: ca75fa55-ff72-4276-b96c-a9db63a66e79
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Date deposited: 05 Jul 2022 00:26
Last modified: 16 Mar 2024 19:59
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Author:
James Dudley Hart
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