Solid phase synthesis of 4-hydroxycinnamic acid and its derivatives for potential use in combinatorial chemistry: a novel route for the synthesis of 4-hydroxycinnamoyl coenzyme A and NMDA receptor antagonists.
Synthesis of 4-hydroxycinnamic acid 6 and its N-hydroxysuccinimide ester 8 has been carried out in high yield on solid support. Further development allowed the synthesis of 4-hydroxycinnamoyl CoA 1 in excellent overall yield. The utility of solid phase as a method for the synthesis of 4-hydroxycinnamic acid derivatives was demonstrated by the synthesis of a number of compounds including the NMDA receptor antagonists, N-(phenylalkyl)cinnamides 9 and 10.
McIntyre
B G
BG
Organic & Biological Section, School of Chemistry, Cantock's Close, University of Bristol, UK.
Martínez Bermejo
F
F
Srivastava
S K
SK
Husbands
S M
SM
Lewis
J W
JW
Crosby
J
J
Simpson
T J
TJ
D000214:Acyl Coenzyme A / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003373:Coumaric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018691:Excitatory Amino Acid Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D011422:Propionates; D016194:Receptors, N-Methyl-D-Aspartate / Q000037:antagonists & inhibitors*
C403206:4-hydroxycinnamoyl-CoA; D000214:Acyl Coenzyme A; D003373:Coumaric Acids; D018691:Excitatory Amino Acid Antagonists; D011422:Propionates; D016194:Receptors, N-Methyl-D-Aspartate; C495469:p-coumaric acid