title: Conformational analysis of some alpha-phenylpropionic acids with anti-inflammatory activity.
abstract: CNDO/2 quantum mechanical conformational calculations, as well as 13C and 1H NMR measurements, have been carried out for the propionic acid residues of 2-(p-isobutylphenyl)propionic acid (ibuprofen) and 2-methyl-2-(p-isobutylphenyl)propionic acid. A relationship between the conformational angle of the propionic acid residue and the anti-inflammatory activity appears to exist. The more open the Ph--C alpha--COOH dihedral angle, the larger the anti-inflammatory activity.
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D002351:Carrageenan; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010666:Phenylpropionates / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D000893:Anti-Inflammatory Agents; D010666:Phenylpropionates; D002351:Carrageenan