Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Compound (Z)-8a has been found to display interesting antiinflammatory activity. In order to prepare derivatives with a wide variety of substituents in the aromatic part of the molecule, a new synthesis of the key intermediates 9a-g was developed starting from thiophene-3-carboxylic acid (11) and substituted benzyl bromides. The conversion of 9a-g to 10a-g follows a known procedure. Ketones 10a-g, on reaction with alkyl (dialkoxy-phosphoryl)acetate, followed by isomer separation and alkaline ester hydrolysis, yielded the desired derivatives (Z)-8a-g and (E)-8a-g. The biologically most interesting compound (Z)-8a is currently undergoing clinical trials.
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