Objective: A series of 2-benzylideneaminonaphthothiazoles were designed and synthesized incorporating the lipo- philic naphthalene ring to render them more capable of penetrating various biomembranes. Methods: Schiff bases were synthe- sized by the reaction of naphtha[1,2-d]thiazol-2-amine with various substituted aromatic aldehydes. 2-(2’-Hydroxy)ben- zylideneaminonaphthothiazole was converted to its Co(II), Ni(II) and Cu(II) metal complexes upon treatment with metal salts in ethanol. All the compounds were evaluated for their antibacterial activities by paper disc diffusion method with Gram positive Staphylococcus aureus and Staphylococcus epidermidis and Gram negative Escherichia coli and Pseudomonas aeruginosa bac- teria. The minimum inhibitory concentrations of all the Schiff bases and metal complexes were determined by agar streak dilution method. Results: All the compounds moderately inhibited the growth of Gram positive and Gram negative bacteria. In the present study among all Schiff bases 2-(2’-hydroxy)benzylideneaminonaphthothiazole showed maximum inhibitory activity and among metal complexes Cu(II) metal complex was found to be most potent. Conclusion: The results obtained validate the hypothesis that Schiff bases having substitution with halogens, hydroxyl group and nitro group at phenyl ring are required for the antibacterial activity while methoxy group at different positions in the aromatic ring has minimal role in the inhibitory activity. The results also indicated that the metal complexes are better antibacterial agents as compared to the Schiff bases. Objective: A series of 2-benzylideneaminaphthachhothiazoles were designed and synthesized incorporating the lipo- philic naphthalene ring to render them more capable of penetrating various biomembranes. Methods: Schiff bases were synthe- sized by the reaction of naphtha [1,2-d] thiazol 2-amine with various substituted aromatic aldehydes. 2- (2’-Hydroxy) ben- zylideneaminaphthalhothiazole was converted to its Co (II), Ni (II) and Cu (II) metal complexes upon treatment with metal salts in ethanol. the compounds were evaluated for their antibacterial activities by paper disc diffusion method with Gram positive Staphylococcus aureus and Staphylococcus epidermidis and Gram negative Escherichia coli and Pseudomonas aeruginosa bac- teria. The minimum inhibitory concentrations of all the Schiff bases and metal complexes were determined by agar streak dilution method. Results: All the compounds Moderately inhibited the growth of Gram positive and Gram negative bacteria. In the present study among all Schiff bases 2- (2’-hydroxy) benzylideneonaphthalhothiazole showed maximum inhibitory activity and among metal complexes Cu (II) metal complex was found to be most potent. Conclusion: The results obtained validated the hypothesis that Schiff bases have substitution with halogens, hydroxyl group and nitro group at phenyl ring are required for the antibacterial activity while methoxy group at different positions in the aromatic ring has minimal role in the inhibitory activity. The results also indicated that the metal complexes are better antibacterial agents as compared to the Schiff bases.