Bondavalli F, Ranise A, Schenone P, Ruggiero E, Berrino L, Giasi M, Marmo E
Farmaco Sci. 1983 May;38(5):318-29. doi: 10.1002/chin.198342215.
The synthesis of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-trans-ol (III) starting from 1,3,3-trimethyl-6-nitrimino-2-oxabicyclo[2.2.2]octane is described. Starting from aminoalcohol (III), a series of N-substituted urethanes (IV) and esters (V), as well as the rigid analogue of acetylcholine (VII), were prepared. A number of compounds (V) and particularly (IV) showed remarkable hypotensive and bradycardic activities in rats, whereas the p-aminobenzoate (V h) showed infiltration anesthesia in mice comparable to that of lidocaine. Antiarrhythmic activity in mice and antiacetylcholine activity in vitro are also reported.
描述了从1,3,3-三甲基-6-硝基亚氨基-2-氧杂双环[2.2.2]辛烷开始合成6-顺式-二甲基氨基-1,3,3-三甲基-2-氧杂双环[2.2.2]辛烷-5-反式-醇（III）的过程。从氨基醇（III）出发，制备了一系列N-取代的氨基甲酸酯（IV）和酯（V），以及乙酰胆碱的刚性类似物（VII）。许多化合物（V），特别是（IV）在大鼠中表现出显著的降压和心动过缓活性，而对氨基苯甲酸酯（V h）在小鼠中表现出与利多卡因相当的浸润麻醉作用。还报道了其在小鼠中的抗心律失常活性和体外抗乙酰胆碱活性。
