267244-46-2Relevant academic research and scientific papers
Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid
Baldwin,Fryer,Pritchardt
, p. 2588 - 2596 (2007/10/03)
A range of new C-4 heteroaromatic acromelic acid analogues has been synthesized in a parallel fashion from (-)-α-kainic acid 1. Protection of the amine and carboxylate groups of 1 followed by ozonolysis gave methyl ketone 8. A silyl enol ether 9, generated regiospecifically from the methyl ketone 8 using "kinetic" conditions, was brominated in situ with phenyltrimethylammonium perbromide to give the key α-bromo ketone 10. Parallel cyclization reactions of bromo ketone 10 with thioamides and thioureas were then performed. The aromatic heterocyclic derivatives 11a-d and 19 produced were deprotected to give the new kainoid amino acids 6a-d and 25 in excellent yield. Compounds 6a and 6c show strong binding to the kainate receptor. Reaction of 10 with alternative condensing agents was also briefly investigated.
Novel C-4 heteroaromatic kainoid analogues: A parallel synthesis approach
Baldwin, Jack E.,Fryer, Andrew M.,Pritchard, Gareth J.
, p. 309 - 311 (2007/10/03)
New C-4 thiazole 4, 5 and aminothiazole 6, 7 kainoid analogues were efficiently synthesised in five steps from commercially available (-)-α-kainic acid 1 and exhibited strong binding to the kainate receptors. A reactive α-bromoketone 10 was generated and
