Solid-phase synthesis of a tyrphostin ether library.
The solid-phase synthesis of a 4500-member (30 x 15 x 10) tyrphostin library is demonstrated utilizing the Irori-directed sorting system. Fmoc-protected PL-Rink resin was used as the solid support. After Fmoc-deprotection, aryl aldehydes were attached to the resin through reductive amination. Acylation of the resulting secondary amines with cyanoacetic acid was followed by a Knoevenagel condensation with phenolic aldehydes. Mitsunobu coupling of primary alcohols to the resin-bound phenols yielded the final library of compounds 1.
Guo
Guihua
G
3-Dimensional Pharmaceuticals, Inc, 8 Clarke Drive, Cranbury, New Jersey 08512, USA.
Arvanitis
Elena A
EA
Pottorf
Richard S
RS
Player
Mark R
MR
D000085:Acetates / Q000737:chemistry; D000215:Acylation; D000447:Aldehydes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors; D020032:Tyrphostins / Q000138:chemical synthesis* / Q000737:chemistry
D000085:Acetates; D000447:Aldehydes; D004791:Enzyme Inhibitors; D004987:Ethers; D020032:Tyrphostins; D011505:Protein-Tyrosine Kinases; C007170:cyanoacetic acid