3-杂环基硫取代-1,3,4,5-四氢-2-氧代-苯并氮杂衍生物的合成  

Synthesis of 3-Thioheterocycloyl-1,3,4,5-tetrahdro-2-oxo-1H-benazepine

作　　者：邱早早[1] 张欢欢[1] 惠新平[1] 许鹏飞[1] 王勤[2] 杜宇平[2] 杨洋[2] 

机构地区：[1]兰州大学化学化工学院功能有机分子化学国家重点实验室,兰州730000 [2]兰州大学生命科学学院,兰州730000

出　　处：《有机化学》2007年第5期607-618,共12页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20572039);教育部"新世纪优秀人才支持计划"(No.05-0880);博士点基金资助项目.

摘　　要：以芳酰肼为原料,合成了一系列3-巯基-5-芳基-1,2,4-三唑、2-巯基-5-芳基-1,3,4-噁二唑和2-巯基-5-芳基-1,3,4-噻二唑,并通过硫原子对3-溴-2-氧代-苯并氮杂3-位上的亲核取代反应将杂环化合物引入了苯并氮杂的结构当中,合成了32个新的苯并氮杂杂环衍生物.为提高其在有机溶剂中的溶解性,在苯并氮杂的N原子上引入乙酸乙酯和乙酸叔丁酯基取代基,合成了36个新衍生物.所有化合物经质谱、核磁共振谱及元素分析确证了结构并初步测定了抗菌活性.3-Thiol-1,2,4-triazole, 2-thiol-1,3,4-oxadiazole and 2-thiol-1,3,4-thiadiazole compounds were synthesized from hydrazides through different ways. By the nucleophilic substitution of S for Br on 3-bromo- 1,3,4,5-tetrahydro-2-oxo- 1H-benazepine, 32 derivatives of tetrahydro-2-oxo- 1H-benazepine were synthesized. In order to improve dissolving ability in organic solvents, other 36 derivatives, which have a substituent of acetate on the 1-N position of benazepine, were also prepared. The structures of these compounds were confirmed by MS, 1H and ^13C NMR spectra and elemental analysis. The primary antibacterial activity test indicated that some of the compounds were effective against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Streptococcus and Candida albicans.

关 键 词：苯并氮杂[艹卓] 杂环化合物 亲核取代反应 抗菌活性 

分 类 号：O621.3[理学—有机化学]