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Synthesis and pharmaceutical importance of 2-azetidinone derivatives of phenothiazine

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Abstract

A new series of N-[3-(10H-phenothiazin-1-yl)propyl]-4-(substituted phenyl)-3-chloro-2-oxo-1-azetidinecarboxamide 4(a–m) have been synthesized from phenothiazine in four steps. Phenothiazine on reaction with Cl(CH2)3Br at room temperature gave 1-(3-chlorophenyl)-10H-phenothiazine, 1. The compound 1 yielded the condensation product with urea at room temperature, N-[3-(10H-phenothiazin-1-yl)propyl]urea 2. The compound 2 on further reaction with several substituted aromatic aldehydes produced N-[3-(10H-phenothiazin-1-yl)propyl]-N′-[(substituted phenyl)methylidene]-urea 3(a–m). The compounds 3(a–m) on treatment with ClCH2COCl in the presence of Et3N furnished final products 4(a–m). The structures of all the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and FAB-Mass spectra and chemical methods. All the final synthesized compounds were evaluated for their antibacterial, antifungal and antitubercular activities which displayed acceptable activities.

A new series of N10-3-{(4-substituted aryl-3-chloro-2-oxo-azetidine)-carbamyl}-propylphenothiazine, compounds 4(a–m) were synthesized and screened for their antibacterial, antifungal and antimycrobial activities in vitro.

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Authors and Affiliations

  1. Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H S Gour University (A Central University), Sagar, 470 003, India

    RITU SHARMA, PUSHKAL SAMADHIYA, S D SRIVASTAVA & S K SRIVASTAVA

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  1. RITU SHARMA
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  2. PUSHKAL SAMADHIYA
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  3. S D SRIVASTAVA
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  4. S K SRIVASTAVA
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Correspondence to PUSHKAL SAMADHIYA.

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SHARMA, R., SAMADHIYA, P., SRIVASTAVA, S.D. et al. Synthesis and pharmaceutical importance of 2-azetidinone derivatives of phenothiazine. J Chem Sci 124, 633–637 (2012). https://doi.org/10.1007/s12039-012-0257-x

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  • DOI: https://doi.org/10.1007/s12039-012-0257-x

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