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Journal of Chemical Sciences

, Volume 124, Issue 3, pp 633–637 | Cite as

Synthesis and pharmaceutical importance of 2-azetidinone derivatives of phenothiazine

  • RITU SHARMA
  • PUSHKAL SAMADHIYA
  • S D SRIVASTAVA
  • S K SRIVASTAVA
Article

Abstract

A new series of N-[3-(10H-phenothiazin-1-yl)propyl]-4-(substituted phenyl)-3-chloro-2-oxo-1-azetidinecarboxamide 4(am) 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(am). The compounds 3(am) on treatment with ClCH2COCl in the presence of Et3N furnished final products 4(am). 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.

Graphical Abstract

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.

Keywords

Synthesis 2-azetidinone phenothiazine antimicrobial 

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Supplementary material

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Copyright information

© Indian Academy of Sciences 2012

Authors and Affiliations

  • RITU SHARMA
    • 1
  • PUSHKAL SAMADHIYA
    • 1
  • S D SRIVASTAVA
    • 1
  • S K SRIVASTAVA
    • 1
  1. 1.Synthetic Organic Chemistry Laboratory, Department of ChemistryDr. H S Gour University (A Central University)SagarIndia

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