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Searching new targets for anti-inflammatory drug design, agents with the isoindole skeleton were focused on the basis of preliminary studies of NSAIDs as COX-1 and/or COX-2 enzyme inhibitors. Thus several novel N-substituted isoindoline derivatives as possible biologically active compounds were prepared as analogues of Indoprofen (1) starting from cis-2- [(4-methylphenyl)carbonyl]cyclohexanecarboxylic acid (3) by treatment with primary arylamines.
Certain cycloalkane-anellated heterocycles undergo rearrangement under basic or acidic conditions via ring-contraction, ringexpansion or ring-opening pathways to afford new or unusual compounds. The reactivities and properties of cycloalkane-fused heterocycles differ significantly from those of heteroaromatic ring systems. Possible mechanisms are also discussed.
A simple solvent-free synthesis of 3-[1-(4-methylphenyl)-3-oxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl]propanoic acid 3 was achieved by fusion of cis-2-[(4-methylphenyl)carbonyl]cyclohexanecarboxylic acid 1 with 3-aminopropanoic acid 2. The structure of this new compound was confirmed by elemental analysis, IR, EI-MS, 1H-NMR and 13C-NMR spectral data
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