Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety  

作　　者：YANG Xuan SONG BaoAn JIN LinHong WEI Xue BHADURY S Pinaki LI XiangYang YANG Song HU DeYu 

机构地区：[1]Key Laboratory of Green Pesticide and Agricultural Bioengineering of Ministry of Education,Guizhou University, Guiyang 550025, China [2]National and Local Jointed Engineering Laboratory for Biomass Comprehensive Utilization, Guizhou University, Guiyang 550025, China

出　　处：《Science China Chemistry》2011年第1期103-109,共7页中国科学（化学英文版）

基　　金：the National Key Project for Basic Research (2010CB 126105);the National Natural Science Foundation of China (20872021) for the financial support

摘　　要：Starting from 1-((1R,2R)-2-aminocyclohexyl)-3-substituted thioureas (3a–c) and substituted isothiocyanates (9a–d),chiral bis-thiourea derivatives containing α-aminophosphonate moiety 10a–l were prepared and completely characterized by elemental analysis,physical and spectral (IR,1H NMR,13C NMR,31P NMR) data.The results of bioassay revealed that compounds 10a and 10e possessed appreciable curative bioactivities on cucumber mosaic virus (CMV) at 0.5 mg/mL in vivo (inhibitory rate = 60.3%,64.8% respectively) and tobacco mosaic virus (TMV) at 0.5 mg/mL in vivo (inhibitory rate = 50.3%,50.8% respectively),which were comparable to the values shown by standard reference (58.7%) and commercial product Ningnanmycin (56.3%),respectively.Chiral compound 10e displayed more potent antiviral activity (EC50 = 0.149 mg/mL) than Ningnanmycin (EC50 = 0.201mg/mL) against CMV.Starting from 1-（（1R,2R）-2-aminocyclohexyl）-3-substituted thioureas （3a–c） and substituted isothiocyanates （9a–d）,chiral bis-thiourea derivatives containing α-aminophosphonate moiety 10a–l were prepared and completely characterized by elemental analysis,physical and spectral （IR,1H NMR,13C NMR,31P NMR） data.The results of bioassay revealed that compounds 10a and 10e possessed appreciable curative bioactivities on cucumber mosaic virus （CMV） at 0.5 mg/mL in vivo （inhibitory rate = 60.3%,64.8% respectively） and tobacco mosaic virus （TMV） at 0.5 mg/mL in vivo （inhibitory rate = 50.3%,50.8% respectively）,which were comparable to the values shown by standard reference （58.7%） and commercial product Ningnanmycin （56.3%）,respectively.Chiral compound 10e displayed more potent antiviral activity （EC50 = 0.149 mg/mL） than Ningnanmycin （EC50 = 0.201mg/mL） against CMV.

关 键 词：chiral bis-thiourea α-aminophosphonate moiety antiviral activity SYNTHESIS 

分 类 号：S482.39[农业科学—农药学] O641.6[农业科学—植物保护]