5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮类查尔酮的设计、合成及体外抗肿瘤活性  

Design,Synthesis and In Vitro Antitumor Activities of 5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one Chalcones

作　　者：王璇 李慧[2] 韩潇 毛婷[2] 陈慧琼[3] WANG Xuan;LI Hui;HAN Xiao;MAO Ting;CHEN Hui-qiong(School of Medicine, Wuhan City College, Wuhan 430083, China;Department of Medical Nursing, Changjiang Polytechnic Wuhan 430074, China;Wuhan Aimin Pharmaceutical Limited Company, 436070 ezhou, China)

机构地区：[1]武汉城市学院医学部,湖北武汉430083 [2]长江职业学院医药护理学院,湖北武汉430074 [3]武汉爱民制药股份有限公司,湖北鄂州436070

出　　处：《合成化学》2021年第5期385-393,共9页Chinese Journal of Synthetic Chemistry

基　　金：湖北省普通高等学校人文社会科学重点研究基地湖北技能型人才培养研究中心项目(20BJN012);2017年度湖北省教育厅科研计划项目(B2017578)。

摘　　要：以环己酮、氰乙酸乙酯、硫粉和吗啉为原料,依次通过Gewald反应、关环反应、Chan-Lam偶联反应和Claisen-Schmidt缩合反应以23.9%~40.9%的总收率合成了18个新型5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮类查尔酮化合物,所有化合物结构经过了^(1)H NMR和MS的确证。初步的生物活性测试表明,目标化合物对乳腺癌MCF-7和MDA-MB-231细胞均显示出抑制活性。Eighteen novel 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one chalcones were synthesized from cyclohexanone,ethyl cyanoacetate,sulfur and morpholine via Gewald,Chan-Lam coupling,cyclization and Claisen-Schmidt condensation reactions with a total yield of 23.9%~40.9%.The structures were characterized by the 1H NMR and MS.Their antitumor activities were tested against breast cancer MCF-7 and MDA-MB-231 cells in vitro.The preliminary biological results suggested that these compounds exhibited inhibitory activities against both MCF-7 and MDA-MB-231.

关 键 词：四氢苯并[4 5]噻吩并[2 3-d]嘧啶-4(3H)-酮 查尔酮 Gewald反应 Chan-Lam反应 Claisen-Schmidt缩合反应 抗肿瘤活性 合成 

分 类 号：R914.5[医药卫生—药物化学]