Cyanoacrylate Containing Alkoxy, Cyano Acrylamide And ¦Á-amino Phosphonate Derivatives, And Biological Activity Study

Cyanoacrylate,an important class of bioactive compound,is widely applied in agrochemistry.In our previous work,cyanoacrylates containing pyridyl,chiral aniline moiety,phosphonyl moiety,et.al,have been synthesized,and their activities were evaluated.The resulte shows that these compounds possess high antiviral activities.In 2005,Bing Qingxiao,which showed a remarkable activity against tobacco mosaic virus was developed as a kind ofanti-TMV agant.In order to select cyanoacrylates derivatives with high bioactivity,alkoxyl, amine and a-aminophosphonate moieties were introduced into the structure of cyanoacrylate.42 title compounds were synthesized,among which 12 were alkoxyl cyanoacrylates,6 were amine cyanoacrylates and 24 were a-aminophosphonate cyanoacrylates.The structure of all compounds was confirmed by ¹H NMR,¹³C NMR,IR and elemental analysis.The crystal structure of compoundâ…¢v was confirmed by X-ray diffraction.X-ray intensity data ofâ…¢v listed as followings:the crystal belongs to.orthorhombic crystal system,space group is P2(1)/n, a=10.4331(14) nm,b=12.3900(16) nm,c=21.0677(15) nm,a=90.000°,β=91.193°,γ=90.000°,Z=26,V=2737.0(5) nm³,D_c=1.682 mg/m³,θ=1.91～25.00°,μ=0.961 mm^-1,F(000)=1378,the final least-squares cycle gives R=0.0558,ωR=0.1610.To optimize the reaction conditions,the synthesis of compoundsâ…¢were carried out under several conditions,such as ultrasonic irradiation,microwave irradiation and ion liquid.The microwave irradiation can improve the synthesis.The more viable condition was obtained as following:under microwave irradiation of 0.10 kw,689 kPa at 100℃for 25 minutes,compoundsâ…¢g andâ…¢i were synthesized with high yields 87.8%and 83.4%,respectively.Compared to the classical method,the present one offers several advantages including environmental friend,greener,faster reaction rates,fewer byproducts,and higher yields.The result of bioassay showed that most of the compounds exhibit good antiviral activity against tobacco mosaic virus.Compoundâ… a,â… b,â…¢d andâ…¢e possess good curative effects against TMV in vivo with inhibitory rates at 500 mg/L of 60.0%,66.6%,60.2%,and 58.4%,respectively.Their curative activities are higher than that of Ninnanmeisu(55.8%).