SYNTHESIS AND ANTIINFLAMMATORY ACTIVITY OF SOME CURCUMIN ANALOGS

Curcumin (1) forms the diacetoxy (3) and dimethoxy (4) derivatives wit h acetic anhydride-pyridine and diazomethane, respectively. Friedel-Cr aft reaction of 1 with acetic anhydride and alkyl halides in the prese nce of anhydrous aluminium chloride affords the respective acetyl and alkyl substituted products (5-10). The diepoxy (11) and tetrabromo (12 ) analogues are obtained by reacting 1 with H2O2 and bromine, respecti vely. Demethylation of a followed by reduction with HI and red phospho rus furnishes 13. Treatment of 1 with NaBH4 yields a dihydroxy derivat ive (14). The diacetoxy (3), diacetyl (5) and tetrabromo (12) derivati ves show 50, 50 and 48% inhibition in comparison to phenylbutazone (60 %) and curcumin (40%) at 50 mg/kg dose.