SYNTHESIS OF CERTAIN UNSUBSTITUTED, NOMETHYL)-TRICYCLO[5.2.1.0(2,6)]DECANE-8-KETOXIME, AND -(ARALKYL)-TRICYCLO[5.2.1.0(2,6)]DECANE-8-KETOXIME ESTERS AND ETHERS WITH LOCAL-ANESTHETIC AND ANALGESIC ACTIVITIES

The synthesis of series of unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)tricyclo [5.2.1.0(2,6)]decane-8-ketoximes esters and ethers 3a-j, 3a-d, 7a-j and 13a-d from the oxime synthons 2, 6a-e, 12a and 12b, respectively, is described. All the obtained compounds d isplayed noticeable local anesthetic potential. Among them, the oximin o ether 4d (ED50 = 0.15 mg/kg) and the oximino ester 3a (ED50 = 0.23 m g/kg) are the most active of the series and possess higher potential t han the reference standards. Some of the target compounds evoked analg esic effect, specially the oximino ether 7i which is the most potent o f the series and is stronger than acetylsalicylic acid but weaker than morphine hydrochloride. (C) 1998 Elsevier Science S.A. All rights res erved.