Non-steroidal anti-inflammatory drugs. III. Structure of indoprofen: 2-[4-(1-oxo-2-isoindolinyl)phenyl]propionic acid.
Indoprofen, 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-alpha-methylbenzeneaceti c acid, C17H15NO3, a non-steroidal anti-inflammatory agent, falls into the class of phenylpropionic acids that includes ibuprofen, ketoprofen and flubirprofen. It adopts a planar conformation apart from the carboxylic acid group. There is a small twist of 8.8 (2) degrees between the mean planes of the isoindolinyl and phenyl rings. The rotation of the carboxyl group out of the plane of the adjacent phenyl ring seems to be connected with anti-inflammatory activity and is similar to that found in other 2-phenylpropionic acids. A pair of intermolecular hydrogen bonds connects two carboxylic acid groups across a centre of symmetry with an O...O distance of 2.61 (1) A.
Ravikumar
K
K
Laboratory of Crystallography, Indian Institute of Chemical Technology, Hyderabad.
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D006860:Hydrogen Bonding; D007216:Indoprofen / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007216:Indoprofen