Synthesis And Antibacterial Performance Of The Imide Derivative FPCTO

At present,the frequent use of antimicrobial agents makes the drug resistance of bacteria increase continuously,which is a greatly threat to human health and the development of agriculture and animal husbandry.In view of this,it is of great application significance to develop lead compounds with antibacterial activity and can avoid bacterial resistance.Heterocyclic compounds have been paid highly attention by researchers for their high activity,low toxicity,easy modification and high internal absorption conductivity.Among many heterocyclic compounds,imide derivatives have become research hotspot because of its advantages such as high efficiency,stability,easy storage,and non-toxicity.In this thesis,an imide derivative was designed and synthesized,and its antibacterial performance was studied.The main research contents were as follows:(1)The chalcone derivative FPPO through Claisen-Schmidt condensation reaction with 2-acetylfuran,benzaldehyde as raw materials,KOH as catalyst in this reation.The structure and composition of FPPO was characterized by FT-IR,1H NMR,13C NMR and EA.At the same time,the optical properties and thermal stability of the FPPO were studied using UV,FS,DSC and TGA,respectively.The effect of reaction temperature,reaction time,n(benzaldehyde):n(2-acetylfuran),KOH mass fraction and other factors on the yield of FPPO were explored.Based on this,The technological parameters of FPPO were optimized by using experiment design principle of response surface methodology.The results show that when 6 g of PEG-400 is added to the reaction system,the yield can be increased to 88.53%,which is 8%higher than that reported in the literature.(2)The episulfide compound TFPO was synthesized through one-pot reaction with FPPO,H2O2,thiourea as the raw material,and TBAB as the catalyst in this reation.The structure and composition of TFPO was characterized by 1H NMR,13C NMR and EA.The light transmission properties and thermal stability of TFPO were studied by UV and TGA.After examining the influence of factors such as time,temperature,amount of oxidant,and amount of catalyst on the yield of TFPO.The technological parameters of TFPO were optimized by the orthogonal optimization method.The final yield is 85.76%.(3)The oxazolidinone derivative FPTO through SN2 reaction with urea and TFPO as raw materials,TsOH as catalyst in this reation.The structure and composition of FPTO was characterized by FT-IR,1H NMR,13C NMR and EA.At the same time,the optical properties and thermal stability of the FPTO were studied using UV,FS and TGA.The influence of each factor on the yield and amine value of FPTO was discussed.Based on this,The technological parameters of FPTO were optimized by using experiment design principle of response surface methodology.The yield is 75.74%and the amine value is 3.21 mg/g.(4)The imide derivative FPCTO through acylation reaction with FPTO and CAC as raw materials,DMAP as acid binding agent in this reation.The structure and composition of FPTO was characterized by FT-IR,1H NMR,13C NMR and EA.At the same time,the optical properties and thermal stability of the FPCTO were studied using UV and TGA.After exploring the influence of reaction temperature,reaction time,n(CAC):n(FPTO),n(DMAP):n(FPTO)and other factors on the yield of FPCTO,the technological parameters of FPCTO were optimized by using experiment design principle of response surface methodology.The final yield is 86.47%.(5)Four pathogenic fungi(Fgr,Clu,Fox and Cgl)were selected as test strains,and the antifungal performance of FPTO and FPCTO was tested by the mycelial growth rate method.The results showed that the fungistatic activity of FPCTO was better than that of FPTO.When the concentration was 250 μg/mL,the bacteriostatic rate of FPCTO reached above 93%.Among them,the activity of inhibiting Clu and Cgl was better than that of carbendazim and chlorothalonil.Four pathogenic bacteria(Eco,Eae,Sau and Sep)were selected as test bacteria,and the antibacterial properties of FPTO and FPCTO were evaluated by the filter paper method.The results show that the antibacterial activity of FPCTO is better than that of FPTO.When the concentration is 320 μg/mL,the diameter of the antibacterial circle of FPCTO reaches more than 33 mm,which shows strong inhibition and extreme sensitivity to all four pathogenic bacteria.The inhibitory effect is better than penicillin sodium and chlortetracycline.The antibacterial mechanism of FPTO and FPCTO was discussed.By using the Material Studio software and GGA/BLYP methods,the molecular geometric configurations of FPTO and FPCTO were optimized and the parameters of HOMO,LUMO,and charge distribution were calculated at the DND level.The relationship between the structure of the compound and the antibacterial activity was described.The results show that both FPTO and FPCTO form an electronic relay system,and the antibacterial active center is located on a five-membered substitution containing N,O,and S atoms.And due to the influence of the three-dimensional configuration,EHOMO,χ,σ and other quantum chemical parameters,the contact between FPCTO and bacteria is easier and can be permanently adsorbed on the cell membrane,which effectively inhibits the normal life activities of microorganisms,and finally results in the antibacterial activity of FPCTO being better than FPTO.