The synthesis of 4-arylsulfanyl-substituted kainoid analogues from trans-4-hydroxy-L-proline.
The potent neuroexcitatory activity of kainoid amino acids in the mammalian CNS places new analogues in high demand as tools for neuropharmacological research. A range of 4-arylsulfanyl-substituted kainoids has been synthesised in a parallel fashion via mesylate displacement by a number of aromatic and heteroaromatic thiolates upon (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfo nyloxy pyrrolidine-2-carboxylic acid methyl ester 8, which is obtainable in eight steps from trans-4-hydroxy-L-proline 5.
Baldwin
J E
JE
The Dyson Perrins Laboratory, University of Oxford, UK. jack.baldwin@chem.ox.ac.uk
Pritchard
G J
GJ
Williamson
D S
DS
D006909:Hydroxyproline; D007608:Kainic Acid / Q000138:chemical synthesis*; D018092:Kainic Acid Receptors / Q000187:drug effects
D006909:Hydroxyproline; D007608:Kainic Acid; D018092:Kainic Acid Receptors