3-乙酰基香豆素肟衍生物的合成及抗肿瘤活性  

Synthesis and Anticancer Activity of 3-Acety-coumarin Oxime Ethers Derivatives

作　　者：尚飞扬 张强 冯贝贝 何黎琴 SHANG Fei-yang;ZHANG Qiang;FENG Bei-bei;HE Li-qin(College of Pharmacy,Anhui University of Chinese Medicine,Hefei 230038,China)

机构地区：[1]安徽中医药大学药学院,安徽合肥230038

出　　处：《化学试剂》2021年第1期121-125,共5页Chemical Reagents

基　　金：安徽省教育厅自然科学重点科研项目(KJ2017A292)。

摘　　要：以水杨醛为起始原料,经Knoevenagel反应得到3-乙酰基香豆素,将其酮羰基与盐酸羟胺反应得到肟,利用肟羟基与不同碳数的二溴烷烃反应得到相应的溴代肟醚,再与硝酸银反应得到5个3-乙酰基香豆素肟硝酸酯杂合物。目标化合物的结构经红外光谱、核磁共振氢谱和质谱确证。用检测灵敏度高的CCK-8法评价了目标化合物对人肝癌HepG2细胞、人前列腺癌22RV1细胞、人胃癌HGC-27细胞及人肺癌A549细胞增殖的影响,结果显示3-乙酰香豆素肟硝氧丁基醚对受试的HepG2、HGC-27癌细胞具有较强的增殖抑制作用。3-Acetyl-coumarin was obtained from salicylaldehyde and ethyl acetoacetate by the Knoevenagel reaction,which was then treated with NH2OH to afford 3-acetyl-coumarin oxime.3-Acetyl-coumarin oxime treated with dibromoalkanes in the presence of K_(2)CO_(3) to provide the compounds 3-acethlcoumarin oxime bromoalkyl ether,these compounds were then reacted with silver nitrate to give the target compounds 3-acety-coumarin oxime ethers derivatives.The chemical structure of target compounds was confirmed by ^(1)HNMR,IR,and HR-MS.The in vitro antiproliferative activities of the synthesized compounds were assessed against human cancer cell lines(HepG2,22 RV1,HGC-27 and A549).Among them,compound(E)-4-(((1-(2-oxo-2H-chromen-3-yl)ethylidene)amino)oxy)butyl nitrate exhibited good cell proliferation inhibition in HepG2 and HGC-27 cell lines according to the CCK-8 assay.

关 键 词：癌症 3-乙酰基香豆素 肟醚 硝酸酯 增殖抑制 

分 类 号：R916[医药卫生—药学]