Synthesis of ether oligomers

Org Lett. 2004 Feb 5;6(3):397-400. doi: 10.1021/ol036300d.

Abstract

[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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Chymotrypsin / antagonists & inhibitors
  • Ethers / chemistry*
  • Ketones / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Oximes / chemistry*
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Subtilisin / antagonists & inhibitors
  • Trypsin / metabolism

Substances

  • Aldehydes
  • Ethers
  • Ketones
  • Oximes
  • Protease Inhibitors
  • Chymotrypsin
  • Trypsin
  • Subtilisin