The Polyhalogenated Isophthalonitrile Derivatives The Synthesis And Antibacterial Activity

Anilines, sulfonamides and ethers possess good antibacterial, herbicidal and other biological activities. Halogen-containing compounds, especially fluorinated compounds may greatly increase the biological activities due to the molecular thermal stability, oxidation resistance and electrical effects which have very highly improvement effect by fluorine atoms. These compounds have a wide range of applications in pharmaceutical, pesticide and others fields.In this paper, twenty-five of multi-halogenated isophthalodinitrile derivatives 18, 19 and 20 were synthesized by one step reaction of the readily available starting materials multi-halogenated isophthalodinitrile 16 with amines 17 in the base condition. With the same method, multi-halogenated isophthalodinitriles reacted with alcohols 21 and sulfonamide 23 to obtain four multi-halogenated phenol-ether isophthalodinitriles 22 and four multi-halogenated sulfonamide isophthalodinitriles 24. The synthetic method had the advantages of simple, easily work-up and efficient, etc. All the structure of target compounds were characterized by IR,1H NMR,13C NMR and MS spectra.Four pathogenic bacteria and a pathogenic fungus for drug susceptibility were selected to test the antibacterial activities of all new synthesized compounds. The results showed that these compounds possess good activity on the Gram-positive bacteria. Among them,18g (1.27μg/mL),19a (0.8μg/mL),19b (26.0μg/mL),19c (20.8μg/mL),20b (20.8μg/mL) and 20c (26.0μg/mL) had better activity against staphylococcus aureus (SA), while 19a (2.6μg/mL),19b (20.8μg/mL) and 19c (10.4μg/mL) possess better activity against the wax sample bacillus (BC), and the antimicrobial activities very close to the Noroxin (Nf). As a whole, the antimicrobial activity of 19a (0.8-2.6μg/mL) is the best, evenly matched with commodity medicine of Noroxin (Nf) (0.5-2μg/mL).