Solid-phase synthesis of an N-(phenylalkyl)cinnamide library via Horner-Wadsworth-Emmons reaction

A readily automated solid-phase approach to the synthesis of diverse N-(phenylalkyl)cinnamides, analogues of the NR2B antagonist 2, is described. The procedure utilizes polymer supported N-(phenylalkyl)amines, (diethylphosphono)acetic acid and a wide range of commercially available hydroxybenzaldehy...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-03, Vol.14 (5), p.1279-1281
Main Authors: WEBER, Csaba, BIELIK, Attila, SZENDREI, Györgyi I, KESERU, György M, GREINER, Istvan
Format: Article
Language:English
Subjects:
Biological and medical sciences
Cinnamates - chemical synthesis
Excitatory Amino Acid Antagonists - chemical synthesis
Glutamatergic system (aspartate and other excitatory aminoacids)
Indicators and Reagents
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacology. Drug treatments
Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors
Structure-Activity Relationship
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Summary:A readily automated solid-phase approach to the synthesis of diverse N-(phenylalkyl)cinnamides, analogues of the NR2B antagonist 2, is described. The procedure utilizes polymer supported N-(phenylalkyl)amines, (diethylphosphono)acetic acid and a wide range of commercially available hydroxybenzaldehydes. The key step, a Horner-Wadsworth-Emmons reaction is achieved under mild conditions and was found to be general for a large number of benzaldehydes. A 225-member focused library was synthesized using a Tecan Combitec synthesizer.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2003.12.038