含噻二唑环吡唑并[3,4-d]嘧啶类含氟衍生物的合成及抗菌活性  

Synthesis and Antibacterial Activity of Fluorinated Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole

作　　者：杨平[1,2] 邵宇[2] 宋新建[1,2] 

机构地区：[1]湖北民族学院生物资源保护与利用湖北省重点实验室,湖北恩施445000 [2]湖北民族学院化学与环境工程学院,湖北恩施445000

出　　处：《精细化工》2013年第8期856-859,952,共5页Fine Chemicals

基　　金：湖北省自然科学基金(2011CDB087);湖北省教育厅青年项目(D20111904)~~

摘　　要：通过5-氨基-4-氰基-1-苯基-1H-吡唑与三氟乙酸、三氯氧磷反应"一锅法"制得1-苯基-6-三氟甲基-4-氯-1H-吡唑并[3,4-d]嘧啶,收率为61%,再与5-芳基-2-巯基-1,3,4-噻二唑发生芳香族亲核取代反应合成8种含噻二唑环吡唑并[3,4-d]嘧啶类含氟衍生物,收率为79%～87%。目标化合物的结构经红外光谱、核磁共振氢谱、质谱与元素分析表征。并将其用于两种细菌(金黄色葡萄球菌和大肠埃希菌)的抑菌实验研究。结果表明,该类化合物对金黄色葡萄球菌均有抑制作用,其中化合物Ⅳb和Ⅳh的抑制活性相对较高。Eight fluorinated pyrazolo [ 3,4-d ] pyrimidine derivatives containing 1,3,4-thiadiazole were synthesized in the yields of 79% - 87% by SNAr reaction of 5-aryl-2-mercapto-1,3,4-thiadiazoles with 4-chloro-l-phenyl-6-trifluoromethyl-1H-pyrazolo [ 3,4-d ] pyrimidine, which were efficiently prepared from 5-amino-4-cyano-1l-phenyl-lH-pyrazole, trifluorocetic acid and triehlorophosphate by one-pot procedure in 61% yield. The structures of the products were confirmed by IR,1HNMR, MS and elemental analysis. The primary antibacterial activity of these compounds against two bacteria （Staphylococcus aureus and Escherichia coli ） was screened. The results indicate that the title compounds exhibit antibacterial activity against Staphylococcus aureus, and compounds Ⅳ b and Ⅳ h have relatively good bacteriostatic effect.

关 键 词：吡唑并[3 4-d]嘧啶 1 3 4-噻二唑 含氟化合物 抗菌活性 功能材料 

分 类 号：R914.5[医药卫生—药物化学]