Several analogues (21 and 29-50) of exo-3-phenylbicyclo[3.2.1]oct-3-en-2-amine (1) were prepared, a compound that had been found to have marked antinociceptive activity in the inflamed-paw pressure test in rats. Two synthetically versatile methods leading to these compounds are described. In this series, antinociceptive activity increases with increasing size of the amine substituent, reaching an optimum
制备了exo-3-phenylbicyclo [3.2.1] oct-3-en-2-amine(1)的几种类似物(21和29-50),该化合物已发现在发炎的小鼠体内具有明显的镇痛作用。大鼠足压测试。描述了导致这些化合物的两种合成通用方法。在该系列中,抗伤害感受活性随胺取代基大小的增加而增加,在N(Me)Et(32)时达到最佳值,但这始终与中枢神经系统(CNS)刺激活性有关。这些化合物的抗伤害感受活性很可能是由于与苯
丙胺相似的作用,而不是与鸦片受体的相互作用所致。内非对映异构体22和苯并类似物11均没有抗伤害感受和CNS刺激活性。