Novel C-4 heteroaromatic kainoid analogues: a parallel synthesis approach.
New C-4 thiazole 4, 5 and aminothiazole 6, 7 kainoid analogues were efficiently synthesised in five steps from commercially available (-)-alpha-kainic acid I and exhibited strong binding to the kainate receptors. A reactive alpha-bromoketone 10 was generated and reacted with thioamides and thioureas to form thiazole and aminothiazole heterocycles 11-14. Deprotection gave the new kainoid amino acids 4-7 in excellent yield.
Baldwin
J E
JE
The Dyson Perrins Laboratory, Oxford, UK. jack.baldwin@chem.ox.ac.uk
Fryer
A M
AM
Pritchard
G J
GJ
D007608:Kainic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D007608:Kainic Acid