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Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2'-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2007年第6期8卷 446-452页

作者： AZAM Faizul SINGH Satendra khokhra sukhbir lal PRAKASH Om Department of Pharmaceutical Sciences Kurukshetra University Kurukshetra Haryana 136119 India Faculty of Pharmacy Seventh of October University P.O. Box 2909 Misurata Libya B. R. Ambedkar Center for Biomedical Research University of Delhi Delhi 110007 India Dr. Department of Pharmaceutical Sciences Kurukshetra University Kurukshetra Haryana 136119 India

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.

关键词： Schiff碱石脑油金属配合物合成抗菌作用 2-亚苄基氨基萘噻唑

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