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Synthesis of Novel 2-Azetidinones as Antibacterial Agents | ||
| Al-Zahraa Journal for Health and Medical Sciences | ||
| Article 2, Volume 3, Issue 2, June 2025, Pages 9-35 PDF (2.05 M) | ||
| Document Type: Research Article | ||
| Abstract | ||
| Amino function of 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol (1) has been diazotized by hydrochloric acid and sodium nitrite. The generating oxadiazolyldiazonium chloride was directly reacted with sodium phenoxide of salicylaldehyde affording azo compound (2) that containing aldehyde function. Compound (2) has been condensed with aromatic amines (o-methoxyaniline, 2,4-dimethylaniline, p-aminophenol, o-chloroaniline, 2,4-dichloroaniline, and m-nitroaniline) utilizing microwave method in ethyl alcohol to give the imine compounds (3a-f), correspondingly. Cyclization reaction of Schiff bases and Chloroacetyl chloride usage microwave method in dimethylformamide gave easy Azetidin-2-one derivatives (4a-f), both Gram-negative and Gram-positive bacteria were used to assess the antibacterial properties of azetidinone molecules. The findings indicated that azetidinone derivatives (4a, 4b, and 4d) have more efficacy against Gram-negative bacteria than the common antibiotic amoxicillin-clavulanate, whereas all derivatives (4a-f) appeared less impact than the control drug athwart Gram-positive bacteria. Due to the growing resistance of bacteria to conventional antibiotics, there is a pressing need to develop new antimicrobial agents with novel structural features. In this context, the objective of this research was to synthesize and characterize a series of novel 2-azetidinone derivatives bearing 1,3,4-oxadiazole rings and evaluate their antibacterial activity. The compounds were synthesized using microwave-assisted methods, which is solvent-free, green processes that align with sustainable and eco-friendly chemistry principles. | ||
| Keywords | ||
| Azetidin-2-ones; Microwave technique; Cycloadditions; Chloroacetyl chloride; Antibacterial test | ||
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