顺、反-α-溴代桂皮酰胺类化合物的合成与抗惊活性关系的研究

通过苯环上有取代基的α,β-二溴苯丙酰氯与适量另丁胺或异丙胺反应,得近于等量的α-溴代桂皮酰胺顺、反异构体。用此法并经薄层层析分离得间氯-α-溴代桂皮酰另丁胺等10对顺、反几何异构体,其中以对溴-和对氯-顺式-α-溴代桂皮酰另丁胺的抗惊作用(MES)较强。药理实验表明,这些异构体的构型、苯环及酰胺氮上的取代基对其生物活性都有一定影响。

Studies on the synthesis and anticonvulsant activities of cis and trans-alpha-bromocinnamamides

α, β-Dibromophenyl propionyl chloride with substituents on the phenyl ring reacts with sec-butylamine or isopropylamine at a ratio of 1:4.5 (mole). The reaction would be favourable to the formation of a mixture containing almost equal amount of cis and trans geometrical isomers. By this method and preparative TLC, ten pairs of geometric isomers such as m-chloro-α-bromo-N-sec-butylcinnamamides were obtained. The anticonvulsant activities of cis-p-bromo and p-chloro-α-bromocinnamoyl sec-butylamine were found to be more potent than those of the others. Pharmacological evaluation showed that the configuration of these isomers displayed important effect on the anticonvulsant activity. Besides, the substituents on the phenyl ring and the nitrogen of amide had some influence too.