Synthesis And Biological Activity Of Carbazole Or Myroline Derivatives Containing Isopropanolamine Substructure

Carbazole derivatives exert broad-spectrum biological activities in medicine and pesticides.Based on the our previous study of carbazole derivativies,In this paper,synthetic compound I₁(1-(9H-carbazol-9-yl)-3-(((1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl)methyl)amino)propan-2-ol)was further substituted by group of NH,and modificated by introducing configuration.The mode of mechanism of compound I₁was further investigated.Moreover,The 3,6-disubstituented carbazole was reacted with epichlorohydrin bearing with different configurations to obtain the intermediate.Then,the corresponding intermediate was reacted with different amines containing different configurations to achieve the corresponding taget compounds.The action mechanism of target compounds were further investigated.Furthermore,natural harmine and its derivatives was reported in the field of medicine.To investigate the antibacterial activity of harmine derivatives,a series of harmine derivatives bearing with the scaffold of isopropanol amino were designed and synthesized.all of target compounds were confirmed via ¹H NMR,¹³C NMR and HRMS.Subsenquently,the antibacterial activity of target compounds against rice bacterial blight(Xanthomonas oryzae pv.oryzae,Xoo),citrus canker(Xanthomonas axonopodis pv.citri,Xac)and kiwi fruit bacterial canker(Pseudomonas syringae pv.actinidiae,Psa)were evaluated.The outcoming suggested that compound II₂ exerted best anti-Xoo activity(EC₅₀=1.00?g/m L),compound II₆ displayed best anti-Xac activity(EC₅₀=2.41?g/m L)and compound II₉ exhibited the best anti-Psa activity(EC₅₀=4.25?g/m L).In vivo anti Xoo activity of compound I₁ was evaluated through the leaf-cutting method.Notably,compound I₁ exhibited the better protective activity(53.23%)than BT(42.51%)and TC(38.26%).In addition,The mechanism of action of title compounds against Xoo and Xac were further investigated.Interestingly,compound I₁ could cause cell apoptosis of Xoo through apoptosis technology.Subsequently,the reactive oxygen species in pathogenic bacteria were increased by affected the compound I₁,and the results were photographed by fluorescence microscope.