Paper
Potential antiinflammatory agents. III. Syntheses of 1-substituted 6-chloro-5-cyclohexylindans as related compounds of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284).
Published Mar 25, 1974 · S. Noguchi, M. Obayashi, S. Kishimoto
Chemical & pharmaceutical bulletin
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Abstract
Some 1-substituted 6-chloro-5-cyclohexylindans : 6-chloro-5-cyclohexyl-1-hydroxy-methylcarbonylindan (5), 1-acetyl-6-chloro-5-cyclohexyl-1-indanol (10), 5-[(6-chloro-5-cyclohexylindan)-1-yl] tetrazole (13) and 6-chloro-5-cyclohexyl-1-methylindan-1-carboxylic acid (14), were prepared as related compounds of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) (1), a potent nonsteroidal antiinflammatory agent. During this work an interesting rearrangement from the acetate (4) of 5 to 3-acetyl-5-chloro-6-cyclohexylindene (6) by acetic acid treatment was discovered and the mechanism of this reaction was proposed.
1-substituted 6-chloro-5-cyclohexylindans show potential as potent nonsteroidal antiinflammatory agents, with potential for further development into pharmaceuticals.
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