Synthesis of ether oligomers.
[structure: see text] Hydroxyaromatic aldehydes and ketones were used as building blocks to prepare ether oligomers. An iterative two-step protocol involving Mitsunobu coupling and carbonyl reduction provided a protecting-group-free route with high yields. Activity screening of an 84-member library against proteases led to the discovery of micromolar inhibitors for trypsin, chymotrypsin, and subtilisin.
Renaudet
Olivier
O
Department of Chemistry and Biochemistry, University of Bern, Switzerland.
Reymond
Jean-Louis
JL
D000447:Aldehydes / Q000737:chemistry; D002918:Chymotrypsin / Q000037:antagonists & inhibitors; D004987:Ethers / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010091:Oximes / Q000737:chemistry*; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020860:Subtilisin / Q000037:antagonists & inhibitors; D014357:Trypsin / Q000378:metabolism
D000447:Aldehydes; D004987:Ethers; D007659:Ketones; D010091:Oximes; D011480:Protease Inhibitors; D002918:Chymotrypsin; D014357:Trypsin; D020860:Subtilisin