摘要
以4-氨基-5-[2-(4-氯苯氧甲基苯并咪唑)-1-亚甲基]-3-巯基-1,2,4-三唑(6)和不同的芳香酸为原料,在三氯氧磷的作用下环化合成了17个新型3-[2-(4-氯苯氧甲基苯并咪唑)-1-亚甲基]-6-芳基-1,2,4-三唑[3,4-b]-1,3,4-噻二唑衍生物7.利用IR,1HNMR和元素分析对新化合物6和7的结构进行了表征.初步的生物活性实验结果表明,化合物7a和7b在20μg/mL时对大肠杆菌甲硫氨酰氨肽酶(EcMetAP1)具有较高的抑制活性,抑制率分别为87.26%和82.62%,化合物7f,7h和7l具有中等的抑制活性.化合物7a～7q在20μg/mL时对细胞分裂周期(cdc25B)磷酸酯酶均具有抑制活性,其中化合物7b,7g和7i在5μg/mL时仍具有很高的抑制活性,抑制率分别为98.76%,83.87%和90.57%.杀菌、杀虫、除草和植物生长调节活性筛选测定实验结果表明,所测试的目标化合物7d～7e,7h～7m和7o～7q均无活性.
Seventeen novel 6-aryl-3-[2-（4-chlorophenoxymethylbenzimidazole）-1-methylene]-1,2,4-tria- zolo[3,4-b]-1,3,4-thiadiazoles 7 were synthesized by the condensation of 4-amino-5-[2-（4-chlorophenoxy-methylbenzimidazole）-1-methylene]-3-mercapto-1,2,4-triazole （6） with various aromatic acids in the presence of phosphorous oxychloride. The structures of the intermediate 6 and the target compounds 7 were characterized by IR, 1H NMR techniques and elemental analysis. Preliminary bioassay indicated that the target compounds 7a and 7b exhibited higher inhibitory activity to EcMetAP1 with the inhibition of 87.26% and 82.62% respectively, compounds 7f, 7h and 7l showed moderate activity at the concentration of 20 μg/mL. The compounds 7a～7q had obvious inhibition to the cell devision cycle 25B phosphatase at 20 μg/mL and the compounds 7b, 7g and 7i still had higher inhibition even at 5 μg/mL with the inhibition of 98.76%, 83.87% and 90.57% respectively. The results of screening for fungicidal, insecticidal, herbicidal and plant growth regulating activities indicated that the tested target compounds 7d～7e, 7h～7m and 7o～ 7q all showed no activities.
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
2010年第16期1577-1584,共8页
Acta Chimica Sinica
基金
辽宁省自然科学基金(No.20102126)
辽宁省教育厅高等学校科研基金(No.2008345)资助项目
关键词
三唑并噻二唑
合成
表征
生物活性
triazolo-thiadiazoles
synthesis
characterization
bioactivities
