3,4-二氢-4-芳基香豆素类化合物的合成及其生物活性研究

目的 设计合成一系列3,4-二氢4-芳基香豆素类化合物,并评价其抗氧化、抗肿瘤活性.方法 以取代苯甲醛为原料,经缩合及Ponndorf反应制得目标化合物.采用DPPH法测定目标化合物的抗氧化活性;采用MTT法以胃癌细胞BGC-823为测试细胞株对目标化合物进行体外抗肿瘤活性评价.结果 与结论合成了10个新的3,4-二氢...

Synthesis and pharmacological activities of 4-aryl-3,4-dihydrocoumarin derivatives

4-Aryl-3,4-dihydrocoumarins（neoflavones） represent a minor class of natural compounds which based on the C6—C3—C6 skeleton with an characteristic aryl group in the 4 position.Structurally,4-aryl-3,4-dihydrocoumarins can also be regarded as the hybrids of isoflavones and coumarins,thus being expected to possess corresponding bioactivity.In this paper,ten 4-aryl-3,4-dihydrocoumarins were synthesized by two steps.The first condensation of substituted benzaldehydes and malonic acids in the presence of pyridine and piperidine at 70-90 ℃ gave the expected cinnamic acids in good yields.Then condensation of substituted cinnamic acids with appropriate phenols in the presence of BF3-Et2O and POCl3 gave the target molecule at room temperature.Their structures were confirmed by EI-MS,IR and 1H-NMR.The antioxidant and antitumor activity of these compounds were evaluated by DPPH and MTT assay,respectively.Some of 4-aryl-3,4-dihydrocoumarin derivatives showed strong scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radical：（±）-7,8-dihydroxy-4-（3-hydroxy-4-methoxyphenyl）-3,4-dihydrocoumarin（3c） EC50=（2.69±0.09） μmol · L-1,（±）-7,8-dihydroxy-4-（4-methoxyphenyl）-3,4-dihydrocoumarin（3g） EC50=（2.32±0.10） μmol · L-1 and weak antitumor in vitro activity against BGC-823 cell line（±）-7,8-dihydroxy-4-（3-hydroxy-4-methoxyphenyl）-3,4-dihydrocoumarin（3c） IC50=（136±21） μmol · L-1].The results showed that the 4-arylcoumarins which possessing the catechol moiety may be a beneficial scaffold for therapeutic purpose.