Three racemic esters based on the 1,5-diarylpyrrole structure, which proved to be highly selective COX-2 inhibitors endowed with an appreciable anti-inflammatory activity in some animal models, were subjected to chiral resolution. Their absolute configurations were assigned by comparison of the CD spectrum measured on-line with a HPLC-CD detector, with that calculated by means of a TDDFT method. (c) 2007 Elsevier Ltd. All rights reserved.