The synthesis and antimicrobial study of some azetidinone derivatives with the para-anisidine moiety

Abstract

Azetidinones were synthesized from p-anisidine in two steps. First the Schiff's bases were prepared by reacting the hydrazide of an anisidine derivative with different aromatic aldehydes. Cyclocondensation of the Schiff's bases with chloroacetyl chloride in the presence of triethylamine resulted in the formation of the corresponding azetidinone analogues. The structures of the newly synthesized compounds were confirmed by IR, 1 H NMR and mass spectroscopic analysis. The antibacterial and antifungal potential of the synthesized compounds were evaluated by the agar disc method.

Antibacterial and β‐Lactamase Inhibitory Activity of Monocyclic β‐Lactams

“…Although reported in size of inhibition zones, all compounds were found to be evenly active on all tested strains. Compounds bearing a 4‐chlorophenyl, 4‐nitrophenyl, 4‐dimethylaminophenyl, and 2‐nitrophenyl functionality on side chain R 2 displayed potency against C. albicans that was comparable to that of griseofulvin . The work of Bhat et al .…”

“…Compounds bearing a 4-chlorophenyl, 4-nitrophenyl, 4-dimethylaminophenyl, and 2-nitrophenyl functionality on side chain R 2 displayed potency against C. albicans that was comparable to that of griseofulvin. 167 Table XIV). 168 Biological testing against a multitude of bacterial and fungal strains, including M. tuberculosis, revealed a promising activity against both Gram-positive and Gram-negative bacteria, whereas the fungal strains were unaffected.…”

2-Azetidinone – A new profile of various pharmacological activities

“…Among the tested compound nitro substituents at para position of the phenyl ring on C-4 of 2-azetidinone found to be most potent (Fig. 14) [43]. Mehta et al have synthesized various 4,4 0 -Bis (3-chloro-4-(substituted aryl)-2-oxoazetidin-1-yl) diphenyl sulphone [44].…”

Synthesis of some azetidonone and 1, 3-oxazepine deritives from thymol

“…Azetidine-2-one and 4, 7-oxazepaine derivatives were reported to posse's antibacterial, antifungal (1)(2)(3) , antianflammatory and antitubercular activities (4) also oxazepine derivatives used as neuroleptic and as antidepressant (5,6) Azetidine-2-one can be prepared from ketene-imines cycloaddition (7) reaction, although many synthetic methods have been developed, Bhat and etal. (8) synthesized Schiff's bases from condensation of acid hydrazine of p-anisidine with aromatic aldehydes, which on treatment with chloroacetylchloride in the presences of triethylamine afforded 2-azetidiones.1, 4-benzoxazepine-2, 5-(1H, 3H)-dione was prepared from the reaction of o.aminobenzoic acid with choroacetyl chloride.…”