O-[1-(2-甲基-4-氨基嘧啶-5-甲基)-1H-[1,2,3]-三唑-4-基]甲基取代苯甲酰氨基硫代甲酸酯的合成与生物活性  

Synthesis and Biological Activity of O-[1-(2-methyl-4-aminopyrimidine-5-methyl)-1H-1,2,3-triazol-4-yl]methyl benzoylcarbamothioates

作　　者：谭效松[1] 朱国中[1] 贺红武[1] 

机构地区：[1]华中师范大学化学学院农药与化学生物学教育部重点实验室,湖北武汉430079

出　　处：《化学与生物工程》2016年第11期1-7,共7页Chemistry & Bioengineering

基　　金：国家973计划资助项目(2010CB126100);国家自然科学基金资助项目(20772042)

摘　　要：丙酮酸脱氢酶系（PDHc）属于焦磷酸硫胺素（TPP）依赖性酶,是一个具有重要农学意义的农药作用靶标。以微生物中的丙酮酸脱羧酶E1（PDHc E1）为靶标,设计合成TPP类似物有望发现新型的杀菌活性化合物。以三唑环代替TPP结构中的噻唑环,以异硫氰酸酯结构单元替代TPP结构中的焦磷酸结构单元,设计合成了O-[1-（2-甲基-4-氨基嘧啶-5-甲基）-1 H-[1,2,3]-三唑-4-基]甲基取代苯甲酰氨基硫代甲酸酯类系列化合物Ⅰa~Ⅰj,采用IR、1 HNMR、MS和元素分析对Ⅰa~Ⅰj进行了结构表征,部分化合物还经13 CNMR进一步进行了结构表征。结果表明,此类化合物不仅为大肠杆菌丙酮酸脱羧酶E1（PDHc E1）的抑制剂,而且还显示了杀菌活性。Pyruvate dehydrogenase complex （PDHc） which belongs to thiamine pyrophosphate （TPP）-de- pendent enzyme is an important target for the development of new pesticide. The design and synthesis of TPP analogs are expected to find new antifungal active compounds which target pyruvate decarboxylase EI（PDHc E1） in microorganism. A series of new O- [ 1 - （ 2-methyl-4 -aminopyrimidine- 5 - methyl ） - 1 H- 1,2,3 - triazol-4- yl ） ] methyl benzoylcarbamothioates Ia- Ij were designed and synthesized by introducing triazole ring instead of thiazole ring,and isothiocyanate structural unit replacing pyrophosphate in the structure of TPP. Target compounds were characterized by IR,1 HNMR, MS and confirmed by elemental analysis. Some compounds were also characterized by ^13CNMR spectra. The results showed that compounds Ia-Ij were demonstrated to be Escherichia coli PDHc E1 inhibitors and some compounds exhibited antifungal activity by the bioassay.

关 键 词：丙酮酸脱羧酶 焦磷酸硫胺素 氨基硫代甲酸酯 生物活性 

分 类 号：O627.42[理学—有机化学]