Synthesis of certain unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)-tricyclo[5.2.1.02,6]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 displayed noticeable local anesthetic potential. Among them, the oximino ether 4d (ED50 = 0.15 mg/kg) and the oximino ester 3a (ED50 = 0.23 mg/kg) are the most active of the series and possess higher potential than the reference standards. Some of the target compounds evoked analgesic effect, specially the oximino ether 7i which is the most potent of the series and is stronger than acetylsalicylic acid but weaker than morphine hydrochloride. (C) 1998 Elsevier Science S.A. All rights reserved.