Synthesis And Bacteriostatic Properties Of N-(2-hydroxyphenyl) Benzylamines

Recently, infectious diseases occurred frequently in the world. New infectious diseasessuch as SARS, avian influenza attack human perpetually and old infectious diseases such astuberculosis, social disease, hepatitis, malaria also occurred, which make the need ofantibacterial agent increase hardly. But it is lack of highly effective and safe antibacterialagent to human right now, which restrains the development of infectious disease medicamentofpreventionandcurebadly.On the basis of the spreading mechanism of infectious disease, killing pathogen of thehosetess and environment is a way to cure infectious diseases and to control the spreading ofinfectious diseases. So far, there's only a few kinds of highly effective antibacterial agents.With the rapid development of biochemistry and biologic informatics, the internal structureandpropertyofpathogeny,whichcancauseinfectiousdisease,weredeeplyunderstood.Intheyear of 1998, McMurry from American Tufts University discovered that triclosan killed thebacterium by blocking the synthesis of fatty acid, which proved that the FabI gene ofacyl-ACPreductiveenzyme(ENR)wastheessentialtarget.According to the antibacterial mechanism of triclosan, a series of N-(2-hydroxyphenyl)benzylaminesweredesignedandsynthesized.Thetargetcompoundswereobtainedbytworeactions:N-alkylationanddemethylation.1.N-alkylationN-(2-methoxyphenyl)benzylamines were obtained from the N-alkylation of o-aminophenylmethyl ether and substituted benzylchloride as the raw materials. The reactiveconditions of N-(2-methoxyphenyl)benzylamines were also studied. It shows that the properreaction temperature of each reaction increases gradually when the p-substitutent groupchanges from donor group(eg.–OCH3) to electron-withdrawing group (eg.–NO2). Reactioncannot occurinthepresenceofinorganic acid-bindingagent whenthep-substitutent groupiselectron-withdrawing group. N-(2-methoxyphenyl)benzylamines were characterized by IRand1HNMRandthemax-UVabsorptionwaveofthesecompoundswerealsostudied,etal.2.DemethylationThe N-(2-hydroxyphenyl)benzylamines were obtained by the demethylation of.N-(2-methoxyphenyl)benzylamines The reactive conditions of demethylation were alsostudied. N-(2-hydroxyphenyl) benzylamine were characterized by IR and 1HNMR and themax-UV absorption wave of these compounds were also studied in this paper. ThebacteriostaticspropertiesofN-(2-hydroxyphenyl)benzylamineswerealsoexamined.