(E)-3-苯基丙烯酸衍生物的合成及抗炎活性考察

目的设计合成(E)-3-苯基丙烯酸衍生物,寻找具有较强抗炎活性的化合物。方法对先导化合物(E)-3-[3-甲氧基-4-(3-苯基)丙烯酰氧基]苯基丙烯酸(1)进行结构修饰,将其分别与脂肪(环)醇、芳香醇、芳杂环醇成酯,与脂肪(环)胺、芳香胺、芳杂环胺成酰胺;以二甲苯致小鼠耳肿胀模型考察不同类型的酯和酰胺的抗炎活性。结果合成了8个未见文献报道的(E)-3-苯基丙烯酸衍生物,经红外光谱和核磁共振氢谱确证其结构;目标化合物3a、3b、3c具有一定的抗炎活性,抑制率分别为31.3%、40.3%、31.7%。结论所设计的合成方法可应用于较大分子酯类和酰胺类的合成;在本实验条件下,(E)-3-苯基丙烯酰胺类目标化合物3a、3b、3c具有抗炎作用,高于先导化合物1,(E)-3-苯基丙烯酸酯类目标化合物几乎无抗炎活性。

Synthesis and anti-inflammatory activities of (E)-3-phenylpropcnoic acid derivatives

Objective To design and synthesize(E)-3-phenylpropenoic acid derivatives and study their anti-inflammatory activities.Methods The target compounds were synthesized from(E)-3-[3-methoxy4-(3-phenyl)acryloxy]phenylpropenoic acid via dehydration and their biological activities were evaluated with the model of xylene-induced ear edema in mice.Results Eight novel compounds were obtained and their structures were characterized by 1H-NMR and IR spectra.Pharmacological tests showed the target compound 3a,3b,3c exhibited certain anti-inflammatory activities,the inhibitory rate were 31.3%,40.3%,31.7% respectively.Conclusions The synthetic method can be applied to the synthesis of esters and amides;the anti-inflammation activities of target compounds 3a,3b,3c are higher than that of compound 1.