Macrocyclic chiral receptors toward enantioselective recognition of naproxen

Org Lett. 2006 Oct 12;8(21):4679-82. doi: 10.1021/ol061505i.

Abstract

[structure: see text] A macrocyclic receptor based on a bischromenylurea and an alpha,alpha'-(o,o'-dialkyl)diphenyl-p-xylylenediamine spacer provides a C(2) chiral cavity to associate carboxylates by H-bonds. The extent of the selectivity obtained for the racemic receptor 2 and enantiomerically pure (S)-naproxen is 7.2:1. Steric repulsions close to the cavity are decisive for the chiral selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Crystallography, X-Ray
  • Molecular Conformation
  • Molecular Structure
  • Naproxen / chemistry*
  • Stereoisomerism
  • Urea / analogs & derivatives*
  • Urea / chemistry*
  • Xylenes / chemistry*

Substances

  • Xylenes
  • Naproxen
  • Urea