Synthesis of certain 2-endo-dimethylaminomethyl-1,7,7 - trimethylbicyclo [2.2.1] heptan-2-exo-ol esters with antiinflammatory, anticonvulsant and hypoglycaemic effects

ABSTRACT

The synthesis of certain esters of 2-endo-dimethylaminomethyl-1,7,7- trimethylbicyclo [2.2.1] heptan-2-exo-ol [4a-g] has been performed. These compounds have been evaluated for their antiinflammatory, anticonvulsant and hypoglycaemic potential as well as their ulcerogenic effect. Compounds 4-benzoic acid 2-endo-dimethyfamlnomethyl-1,7,7-trimethylbicyclo [2.2.1] hept-2-exo-yl ester [4a]; 4-bromo-benzoic acid 2-endo-dimethylaminomethyl-l,7,7-trimethylbicyclo [2.2.1] hept-2-exo-yl ester [4c]; 3,4,5 trimethoxybenzoic acid 2-endo-dimethylaminomethyl-l,7,7-trimethylbicycio [2.2.1] hept-2-exo-yl ester [4e] and 4-methoxybenzoic acid 2-endo-dimethylaminomethyl-1,7,7-trimethylbicyclo [2.2.1] hept-2-exo-yl ester [4d] displayed the most potent anti-inflammatory activity, besides being devoid of ulcerogenicity. Moreover, Compounds 4e and 4d exhibited the highest anticonvulsant effect. Compounds 4d and 4a showed almost equal hypoglycaemic properties, but still less than gliclazide as a reference drug