Issue 11, 2001

Binding interactions between 3-aryl-1,2,4-oxadiazol-5-ones and a trisimidazoline base

Abstract

The use of 1,2,4-oxadiazol-5-ones, a recently developed class of bioisosteric replacements for carboxylic acids in medicinal chemistry, as binding ligands in supramolecular complexes is reported and has been exemplified by the formation of non-covalent complexes between acidic 3-aryl-1,2,4-oxadiazol-5-ones and an imidazoline base, 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene 1. The X-ray crystal structure of complex 6d illustrates how the carbonyl oxygen and the nitrogen atom in the position α to the carbonyl group of the heterocyclic ligand are hydrogen-bonded to the NH groups of tris(imidazoline) 1. A combination of 1H NMR dilution studies and electrospray mass spectrometry-based competition experiments shows that 1,2,4-oxadiazol-5-ones bind more strongly to receptor 1 than a comparable benzoate.

Graphical abstract: Binding interactions between 3-aryl-1,2,4-oxadiazol-5-ones and a trisimidazoline base

Supplementary files

Article information

Article type
Paper
Submitted
24 Nov 2000
Accepted
03 Apr 2001
First published
08 May 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1321-1328

Binding interactions between 3-aryl-1,2,4-oxadiazol-5-ones and a trisimidazoline base

A. Reichert, R. Fröhlich, R. Ferguson and A. Kraft, J. Chem. Soc., Perkin Trans. 1, 2001, 1321 DOI: 10.1039/B009451J

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