1-Indancarboxylic acids. II. Synthesis of 4- and 6-aroyl-1-indancarboxylic acids as potential antiinflammatory agents.

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Abstract
6-Aroyl-1-indancarboxylic acids (V) and isomeric 4-aroyl-1-indancarboxylic acids (XVIII) were prepared in an attempt to obtain information on the receptor sites of antiinflammatory aroylarylacetic acids. Compounds V were easily obtained by the Friedel-Crafts reaction of ethyl 1-indancarboxylate and aroyl chloride. Compounds XVIII were synthesized from 1-oxo-4-indancarboxylic acid via the Friedel-Crafts reaction of 1-cyano-4-indancarbonyl chloride (XVI) and benzene or its derivative. Although compounds XVIII showed potent antiinflammatory activity, the activity of V was significantly weaker. Apparently locations and conformations of the functional groups in XVIII are considerably close to the actual conformation of a aroylarylacetic acid required for exerting antiinflammatory activity.