Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action

Organic & Biomolecular Chemistry Pub Date: 2003-05-27 DOI: 10.1039/B302411C

Abstract

13C NMR and mass spectrometry studies have been used to demonstrate that the inhibition of α-chymotrypsin by N-sulfonylhydroxymethylpyrrole inhibitors (10) is non-covalent. Hydroxyalkylpyrroles in which an electron-withdrawing group (acyl substituent) is introduced at the alternative C2 position have been synthesised and also shown to inactivate α-chymotrypsin. SAR studies on this class suggests that the incorporation of phenylalanine at C2 is favoured, however, there is little gain in introducing a hydrophobic substituent at C5.

Graphical abstract: Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action
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