Synthesis and pharmaceutical importance of 2-azetidinone derivatives of phenothiazine

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(CH 2)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-(10Hphenothiazin- 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. © Indian Academy of Sciences.