新型5,6,7,8-四氢苯并噻吩并嘧啶酮衍生物的合成与抗肿瘤活性研究  

Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydrobenzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives

作　　者：王红梅[1] 郭树兵[2] 胡扬根[1,3] 曾小华[1] 杨光义[1,3] 

机构地区：[1]武当特色中药研究湖北省重点实验室湖北医药学院医学化学研究所,十堰442000 [2]湖北医药学院图书馆,十堰442000 [3]湖北医药学院附属太和医院药学部,十堰442000

出　　处：《有机化学》2015年第5期1075-1080,共6页Chinese Journal of Organic Chemistry

基　　金：湖北自然科学基金(No.2011CDC006);湖北省2011协同创新中心基金(No.2011JH-2014CXTT07);湖北医药学院优秀中青年科技创新团队研究(Nos.2011CXX03;2009QDJ15;2014XKJSXJ06)资助项目~~

摘　　要：应用5,6,7,8-四氢苯并噻吩膦亚胺(2)与烷基异氰酸酯的氮杂Wittig反应生成碳二亚胺2,在不同的条件下,2分别与不同的亲核试剂反应,有效地合成了不同取代的新型稠合噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物.所得化合物的结构由1H NMR,IR,MS和元素分析所确证.初步的体外抗肿瘤活性测试,结果显示目标化合物具有抑制肿瘤细胞的生长,其中5d对口腔肿瘤细胞KB2IC50值为19.0μmol/L,表现出潜在的抗肿瘤活性.The aza-Wittig reaction of iminophosphorane 2 with alkyl isocyanates gave carbodiimides 3, which were allowed to react with various nucleophilic reagents under mild condition in satisfactory yields to prepare a novel series of 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4（3H）-one derivatives. The structures of these compounds were confirmed by IH NMR, IR, MS and elemental analysis. The in vitro antitumor activities of compounds were analyzed with 3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyltetrazo-liumbromide （MTT） standard method, 5d stood out as the most potent showing an IC50 of 19.0 μmol/L against human tumor cell lines （KB）.

关 键 词：氮杂WITTIG反应 噻吩并嘧啶酮 合成 抗肿瘤活性 

分 类 号：O626[理学—有机化学] TQ460.1[理学—化学]