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Molecules 2007, 12(11), 2467-2477; doi:10.3390/12112467

Synthesis and Biological Activity of N-Substituted-3-chloro-2-azetidinones

Department of Organic Chemistry, D.G.Ruparel College, Senapati Bapat Marg, Mahim, Mumbai-400016, India
Author to whom correspondence should be addressed.
Received: 31 July 2007 / Revised: 22 October 2007 / Accepted: 31 October 2007 / Published: 12 November 2007
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2-Aminobenzothiazole-6-carboxylic acid (1), on condensation with chloroacetylchloride yielded 2-(2-chloroacetylamino)benzothiazole-6-carboxylic acid (2), which onamination with hydrazine hydrate yielded in turn 2-(2-hydrazinoacetylamino)benzo-thiazole-6-carboxylic acid (3). Compound 3, on condensation with various aromaticaldehydes afforded a series of 2-{2-[N’-(arylidene)hydrazino]acetylamino}benzothiazole-6-carboxylic acids 4a-h, which upon dehydrative annulation in the presence ofchloroacetyl chloride and triethylamine yielded 2-{2-[3-chloro-2-(aryl)-4-oxoazetidin-1-ylamino]-acetylamino}benzothiazole-6-carboxylic acids 5a-h. The synthesized compounds4a-h and 5a-h were screened for their antibacterial activity against four microorganisms:Staphylococcus aureus (Gram positive), Bacillus subtilis (Gram positive), Psuedomonasaeruginosa (Gram negative) and Escherichia coli (Gram negative). They were found toexhibit good to moderate antibacterial activity. The antifungal activity of these compoundswere also tested against three different fungal species. None of them were active againstthe species tested.
Keywords: 2-Aminobenzothiazole; azetidinones; antibacterial activity. 2-Aminobenzothiazole; azetidinones; antibacterial activity.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Chavan, A.A.; Pai, N.R. Synthesis and Biological Activity of N-Substituted-3-chloro-2-azetidinones. Molecules 2007, 12, 2467-2477.

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