Abstract
Two series of N-3-arylpropenyl- N-9-propionyl-3,9-diazabicyclo[3.3.1]nonanes ( 1b– j) and of the reverted N-3-propionyl- N-9-arylpropenyl isomers ( 2b– j) as analogues of the previously reported analgesic N-3(9)-cinnamyl- N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes (DBN) ( 1a, 2a) were synthesised and their affinity and selectivity towards opioid μ-, δ- and κ-receptors were evaluated. Several compounds ( 1e, i, j– 2d, e, f, g, j) exhibited a μ-affinity in the low nanomolar range with moderate or negligible affinity towards δ- and κ-receptors. The representative term N-9-(3,3-diphenylprop-2-enyl)- N-3-propionyl-DBN (2d) displayed in vivo (mouse) a potent analgesic effect (ED 50 3.88 mg/kg ip) which favourably compared with that of morphine (ED 50 5 mg/kg ip). In addition, 2d produced in mice tolerance after a period twice as long with morphine.
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