双-三唑并[3,4-b]-[1,3,4]噻二唑类化合物的合成及抗癌活性研究  

The Synthesis and Anticancer Activities for Bis-Triazolo [3,4-b]-[1,3,4]Thiadiazole Derivatives

作　　者：李永双[1] 李德江[1] 

机构地区：[1]三峡大学化学与生命科学学院,湖北宜昌443002

出　　处：《江西师范大学学报（自然科学版）》2012年第3期297-300,共4页Journal of Jiangxi Normal University(Natural Science Edition)

基　　金：金国家自然科学基金(31100080);湖北省自然科学基金(2011CDB186);湖北省高校产学研合作(C2010027)资助项目

摘　　要：间苯二甲羧酸酯化、肼解、成盐、环化成双-(4-氨基-5-巯基-1,2,4-三唑-3-基)苯(1),再与芳香酸(2a^2m)在相转移催化剂四丁基碘化铵和POCl3作用下,高产率地制得13种1,3-双[(6-芳基)-1,2,4-三唑并[3,4-b]-[1,3,4]噻二唑-3-基]苯类衍生物(3a^3m),并利用IR、1H NMR、MS和元素分析对目标化合物的结构进行了表征.用MTT方法评价了它们在体外对HepG-2、A549-1和231-2癌细胞株的体外生长抑制活性.结果表明:所合成的13个新化合物(3a^3m)均具有潜在的体外抑制癌细胞生长活性,其中3d、3h与3i对HepG2和231-2的体外抑制活性最强.The m-phthaloylhydrazide was prepared by hydrazinolysis of the dimethyl terephthalate. The reaction of terephthaloyl with CS2/KOH in absolute ethanol gave potassium terephthaloyldithiocarbazate and then the reaction of potassium terephthaloyldithiocarbazate with hydrazine hydrate afforded 3-benzyloxyphenyl-4-amino-5-mercapto- 1,2,4-triazole（1）. 1,4-Bis[（6-aryl）-l,2,4-triazolo[3,4-b]-[1,3,4]thiadiazole-3-yl]benzene derivatives 3a^3m were accomplished with good yields by condensing bis-（4-amino-5-mercapto-l,2,4-triazol-3-yl） benzene （1） with dicar- boxylic （2a-2m） acids in the presence of POC13 and tetrabutylammonium iodide as catalyst. The structures of 3a-3m were confirmed by elementary analyses, IR, ^1H NMR, and MS spectra, and their in vitro anticancer activity against the three cancer celllines of HepG-2, A549-1 and 231-2 was evaluated. Compounds 3d, 3h and 3i are highly active against HepG2 and 231-2.

关 键 词：双-1 2 4-三唑并[3 4-b]-[1 3 4]噻二唑 合成 抗癌活性 

分 类 号：O626.24[理学—有机化学]