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以异丁香酚为原料,经氧化银催化的自由基仿生氧化偶联反应,一步合成了天然苯并二氢呋喃新木脂素licarin A(1),然后经2,3-二氯-5,6-二氰基对苯醌(DDQ)氧化脱氢反应得到另一苯并二氢呋喃新木脂素化合物2-(3’-甲氧基-4’-羟基)苯基-3-甲基-5-甲酰乙烯基-7-甲氧基-2,3-苯并二氢呋喃(2).以苯并二氢呋喃新木脂素1和2为底物,以甲醇为溶剂,分别与甲醛、二级胺在酸性介质中发生微波协助的Mannich反应,合成了11个新的苯并二氢呋喃新木脂素Mannich碱衍生物3~13.所合成的化合物通过1HNMR、13CNMR和MS等进行了结构确证,并采用CCK-8法测试了所合成化合物对人宫颈癌Hela细胞株的体外抑制活性.结果表明大部分化合物对Hela细胞增殖具有良好的抑制作用,其中化合物2(IC50 0.438μmol/L)和化合物9(IC50 8.358μmol/L)具有最强的Hela细胞增殖抑制活性.
Using isoeugenol as raw material, the native benzodihydrofuran naringlins licarin A (1) was synthesized in one step by silver oxide-catalyzed free-radical biomimetic oxidative coupling reaction. Then 2,3-dichloro- The oxidative dehydrogenation of 6-dicyano-p-benzoquinone (DDQ) gave the other benzodihydrofuran neolignan compound 2- (3’-methoxy-4’-hydroxy) phenyl-3- -5-formylvinyl-7-methoxy-2,3-benzodihydrofuran (2) .Both of benzodihydrofuran neolignans 1 and 2 as substrate and methanol as solvent respectively Mannich reaction with formaldehyde and secondary amine in microwave assisted synthesis of 11 new benzyldihydromu neolignans Mannich base derivatives 3 to 13. The synthesized compounds were characterized by 1H NMR, 13CNMR and MS Were used to confirm the structure and the inhibitory activity of the synthesized compounds on human cervical cancer Hela cell line was tested by CCK-8 method.The results showed that most of the compounds had a good inhibitory effect on the proliferation of Hela cells, and compound 2 (IC50 0.438 μmol / L) and compound 9 (IC50 8.358μmol / L) had the strongest Hela cell proliferation inhibitory activity.