微波辅助的Ugi反应合成二苯基吡唑取代双酰胺类化合物  

Synthesis of diamide compounds bearing diphenyl-pyrazole via microwave-assisted Ugi reaction

作　　者：侯学会 张友璐 王川川 丁德刚 徐军 张京玉[2] HOU Xue-hui;ZHANG You-lu;WANG Chuan-chuan;DING De-gang;XU Jun;ZHANG Jing-yu(Faculty of Science,Henan University of Animal Husbandry and Economy,Zhengzhou 450046,China;School of pharmacy,Henan University of Chinese Medicine,Zhengzhou 450046,China)

机构地区：[1]河南牧业经济学院理学部,河南郑州450040 [2]河南中医药大学药学院,河南郑州450046

出　　处：《化学研究与应用》2023年第11期2588-2596,共9页Chemical Research and Application

基　　金：河南省自然科学基金项目(202300410264)资助;河南省科技攻关项目(232102111051)资助。

摘　　要：双酰胺类化合物是一类重要的有机化合物,广泛存在于天然产物和生物活性分子中,表现出优异的生物活性和药理活性。本文以二苯基吡唑羧酸、芳胺、异氰化合物及芳香醛为原料,经微波辅助的Ugi反应合成了两类具有潜在TLR4受体激动活性的二芳基吡唑取代的双酰胺类化合物,其结构均经过核磁共振氢谱(1H NMR)、碳谱(^(13)C NMR)和质谱(MS)确证。并以化合物5b的合成为模板反应,考察了影响Ugi反应产率的因素,确定微波辅助的Ugi反应的最佳条件为:以甲醇/二氯甲烷(体积比1:1)为溶剂,微波照射下50℃反应1 h。Diamide scaffolds are prevalent in various natural and bioactive molecules,exhibiting excellent biological and pharmaco-logical activities.In this article,two series of diamide compounds bearing diphenyl-pyrazole with potential TLR4 receptor agonistic activity were synthesized via microwave-assisted Ugi reaction using diphenylpyrazole carboxylic acid,arylamine,isocyanide and aro-matic aldehydes as starting materials.The structures of the target molecules were characterized by^(1)H NMR,^(13)C NMR and MS spec-tra.Taking the synthesis of compound 5b as the model reaction,the factors affecting the yield of Ugi reaction were investigated.The optimal conditions of microwave-assisted Ugi reaction were determined as follows:methanol and dichloromethane(volume ratio was 1:1)was used as the solvent,and the reaction was performed at 50 C under microwave irradiation for 1 h.

关 键 词：Ugi反应 微波 双酰胺 多组分反应 TLR4受体 

分 类 号：O625.75[理学—有机化学]