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 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.
Wéber
Csaba
C
Chemical and Biotechnological Research and Development, Gedeon Richter Ltd., PO Box 27, H-1475 Budapest, Hungary. cs.weber@richter.hu
Bielik
Attila
A
Szendrei
Györgyi I
GI
Keserû
György M
GM
Greiner
István
I
D002934:Cinnamates / Q000138:chemical synthesis*; D018691:Excitatory Amino Acid Antagonists / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D016194:Receptors, N-Methyl-D-Aspartate / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship
D002934:Cinnamates; D018691:Excitatory Amino Acid Antagonists; D007202:Indicators and Reagents; D016194:Receptors, N-Methyl-D-Aspartate