1-取代-4-[5-(4-取代苯基)-1,3,4-噻二唑-2-磺酰基]哌嗪类衍生物的合成及其抑菌活性  

Synthesis and Antibacterial Activities of 1-Substituted-4-[5-(4-substitutedphenyl)-1,3,4-thiadiazol-2-sulfonyl] piperazine Derivatives

作　　者：吴琴[1,2] 王贞超[1] 魏学[1] 薛伟[1] 

机构地区：[1]贵州大学精细化工研究开发中心教育部绿色农药和生物工程重点实验室,贵州贵阳550025 [2]贵州理工学院制药工程学院,贵州贵阳550003

出　　处：《合成化学》2014年第4期429-434,452,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(20762002);国家十二五科技支撑计划资助项目(2011BAE06B04-09)

摘　　要：根据活性亚结构拼接原理,将1,3,4-噻二唑环和哌嗪环通过磺酰基桥接,设计并合成了16个新型的1-取代-4-[5-(4-硝基苯基)-1,3,4-噻二唑-2-磺酰基]哌嗪类衍生物(4a^4p),其结构经1H NMR,13C NMR,IR和元素分析表征。考察了溶剂、缚酸剂和反应温度对1-甲基-4-[5-(4-硝基苯基)-1,3,4-噻二唑-2-磺酰基]哌嗪(4a)产率的影响。合成4a的最佳反应条件为:乙腈为溶剂,三乙胺为缚酸剂,于25℃反应5 h,产率75%。采用生长速率法研究了4a^4p对小麦赤霉菌、苹果腐烂病菌和辣椒枯萎病菌的抑制活性。结果表明:在用药量为50μg·mL-1时,1-(4-氟苄基)-4-[5-(4-硝基苯基)-1,3,4-噻二唑-2-磺酰基]哌嗪(4d)和1-丙炔基-4-[5-(2,4-二氯苯基)-1,3,4-噻二唑-2-磺酰基]哌嗪(4n)对三种病菌均具有较好的抑制活性。Sixteen novel 1-substituted-4-[5-（4-substituted phenyl）-1,3,4-thiadiazol-2-sulfonyl] piperazine derivatives（4a ～ 4p） were designed and synthesized by connection reaction of 1,3,4-thiadiazol with N-substitued piperazine.The structures were characterized by 1H NMR,13C NMR,IR and elemental analysis.Effects of the solvent,acid acceptor and reaction temperature on the yield of 1-methyl-4-[5-（4-nitrophenyl）-1,3,4-thiadiazol-2-sulfonyl] piperazine （4a） were investigated.The optimum reaction conditions for synthesizing 4a with the yield of 75% at 25 ℃ for 5 h were as follows：acetonitrile was solvent and triethylamine was acid acceptor.The antibacterial activities of 4a ～ 4p against G.zeae,C.mandshurica and F.oxysporum were investigated by growth rate method.The results indicated that 1-methyl-4-[5-（4-fluorobenzyl）-1,3,4-thiadiazol-2-sulfonyl] piperazine （4d） and 1-methyl-4-[5-（4-propinyl）-1,3,4-thiadiazol-2-sulfonyl] piperazine （4n） exhibited better antibacterial activities at 50 μg · mL^-1

关 键 词：1 3 4-噻二唑 哌嗪 磺胺 合成 抑菌活性 

分 类 号：O626.25[理学—有机化学] O626.32[理学—化学]