2,4,5,7-取代芳基苯并[b]呋喃类化合物的合成及其抗肿瘤活性

Synthesis and Antitumor Activities of 2, 4, 5, 7-Arylbenzo [b] furan Derivatives

利用3-甲氧基4-苄氧基苯乙炔化亚铜(1)和3-甲氧基4羟基-5-溴肉桂酸甲酯在吡啶中进行缩合反应合成2-(3-甲氧基-4-苄氧基苯基)-5-[2-甲氧基羰基-(E)-乙烯基]-7-甲氧基苯并[b]呋喃(2),2经过催化氢化反应得到化合物3,3进一步通过胺化、乙酰化、还原、水解、Vilsmeier反应、烷基化以及部分去甲基化等反应合成一系列2,4,5,7-取代芳基苯并[b]呋喃类化合物4-15,并通过IR、NMR、MS和元素分析确证了结构。并采用四唑盐比色法试验对部分化合物进行了体外抗肿瘤活性和细胞毒性测试,所测试化合物均显示出明显的细胞毒作用,其中化合物(9)的细胞毒性在所测试化合物中最强,对人口腔上皮癌细胞KB-3-1 IC50为1.71μg/mL, 具有良好的研究前景。

A series of 2,4,5,7-Arylbenzo[ b ] furan derivatives were designed and synthesized by reduction, Vilsmeier reaction, hydrolysis and substitution reaction of 2-（ 3-methoxy-4-hydroxyphenyl ）-5-（ 2-（ methoxycarbonyl ） ethyl）-7- methoxybenzo[ b ] furan. Their structures were fully characterized by IR, NMR, MS and element analysis. Some synthesized 2-arylbenzo [ b ] furans were evaluated in the in vitro human tumor cell screening. Compounds tested showed potential antitumor activity against tumor cell. Among them compound 9 exibited significant cytotoxicity with IC50 value being 1.71 μg/mL against KB-3-1 tumor cell.