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Synthesis of Novel Nitro Substituted Benzothiazole Derivatives and Antibacterial activity against Pseudomonas aeruginosa

The resistance to antimicrobial drugs is becoming an increasingly important health and economic problem, and Pseudomonas (P) aeruginosa , one of the main micro-organisms of nosocomial infections, is known for its resistance to a range of antimicrobial agents. Benzothiazole derivatives have great importance in heterocyclic chemistry because of its potent and significant biological activities especially methoxy substitution at benzothiazole. Methoxy substituted benzothiazole derivatives were synthesized by reaction of 3-chloro-4-methoxy-aniline with potassium thiocyanate under temperature control and presence of bromine in glacial acetic acid and ammonia. Substituted nitrobenzamides then synthesized by condensation of, 2-amino-4-chloro-5-methoxy-benzothiazole with 2(3or4)-nitrobenzoylchloride acid in presence of dry pyridine and acetone. Finally, newly synthesized derivatives (K-01 to K-09) were synthesized through replacing of chlorine of nitrobenzamide by reaction with 2-nitroaniline, 3-nitroaniline, and 4-nitroaniline in presence of DMF. Analytical characterization was performed by TLC, melting point, IR and NMR spectra. Antibacterial activity was performed against P. aeruginosa by cup plate method (diffusion technique) using procaine penicillin as standard. Methoxy substituted benzothiazole derivatives comprising nitro group were synthesized and characterized by using analytical techniques. The synthesized derivatives screened for antibacterial activity. Compound K-03, K-05 and K-06 showed potent antibacterial activity against P. aeruginosa at both concentrations 50µg/ml and 100µg/ml as compared to standard.