Synthesis And Antibacterial Activities Of 5-Substituent-1,2,4-Triazole-3-Thione Glucosides Compounds

In recent years,Enhanced pathogen resistance and mutation resulting in drug inactivation,based on the fact that there is a excellent affinity between O-hydroxyphenyl(oxy)group? substituted triazole ring?schiff bases and nucleosides group molecular fragments and the targets of many kinds of pathogens,Glycosylation?Nucleosides have been bonded to the O-hydroxyphenyl modified Triazoles compounds,and several types of multi-target and multinuclear antimicrobial compounds have been constructed,dedicate to overcome shortage of narrow-spectrum and drug resistance of the mononuclear compoundsAccording to the principle of superposition of bioactive substructures and the resu lts of molecular modeling design.We designed and synthesized 6series of 30 new comp ounds:2-S-2?,3?,4?,6?-tetra-O-acetyl-?-D-glucopyranosyl-4-(N-substituted-phenyl)imino-5-me thyl-1,2,4-triazoles(2R1~2R5)?2-S-2?,3?,4?,6?-tetra-O-acetyl-?-D-glucopyranosyl-4-(N-substi tuted-phenyl)imino-5-methyl-1,2,4-triazoles(3R1~3R5)?5-methy-4-(N-substituted-phenyl)imino-3-S-(?-D-Glucopyranosyl)-1,2,4-triazole(5R1~5R5)?5-methy-4-(N-substituted-phenyl)amido-3-S-(?-D-Glucopyranosyl)-1,2,4-triazole(6R1~6R5)?5-Phenyl(O-hydroxyphenyl)-4-(N-substituted-phenyl)imino-3-S-(?-D-Glucopyranosyl)-1,2,4-triazole(7R1~7R5?8R1~8R5).The structures of all the compounds were confirmed by 1H NMR,13 C NMR IR and HRMS.The synthesis methods and process conditions of various kinds of compounds were systematically studied,the reaction mechanism and the law of key reaction were discussed,and the preparation technology of key intermediates was developed.The preliminary bioassay was carried out based on U.S.National Clinical Laboratory Standards Committee(NCCLS)Minimal Inhibitory Concentration regulation,using Triclosan and Fluconazole as the reference drugs.The in vitro antimicrobial activity data show that all target compounds possess efficient antibacterial activities against Escherichia coli,Staphylococcus aureus,Bacillus subtilis and Monilia albican.Summed up the relationship between molecular structure and compound antimicrobial activity,a number of highly efficient screening of compounds antibacterial activity.Compound 3R4?3R5?8R4?8R5 shows strong antibacterial activity and great development potential.