Journal of Zhejiang University SCIENCE B
ISSN 1673-1581(Print), 1862-1783(Online), Monthly

2007   Vol. 8   No. 6   p. 446~452

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

AZAM Faizul^†1,2, SINGH Satendra³, KHOKHRA Sukhbir Lal¹, PRAKASH Om¹

(¹Department of Pharmaceutical Sciences, Kurukshetra University, Kurukshetra, Haryana 136119, India)
(²Faculty of Pharmacy, Seventh of October University, P.O. Box 2909, Misurata, Libya)
(³Dr. B. R. Ambedkar Center for Biomedical Research, University of Delhi, Delhi 110007, India)
^†E-mail: faizulazam@gmail.com
Received Nov. 29, 2006 revision accepted Jan. 22, 2007

Abstract: Objective: A series of 2-benzylideneaminonaphthothiazoles were designed and synthesized incorporating the lipophilic naphthalene ring to render them more capable of penetrating various biomembranes. Methods: Schiff bases were synthesized by the reaction of naphtha[1,2-d]thiazol-2-amine with various substituted aromatic aldehydes. 2-(2'-Hydroxy)benzylideneaminonaphthothiazole 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 bacteria. 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.

Key words: Schiff bases, Metal complexes, Antimicrobial
doi:10.1631/jzus.2007.B0446             CLC number: Q621.3

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