Synthesis, Characterization, and Study of Antibacterial Activity of Some New Amphiphilic Sulfamethoxazole Derivatives

Document Type : Original Article

Authors

1 Ministry of Education, The General Directorate of Educational in Najaf Al-Ashraf, Najaf, Iraq.

2 Department of Chemistry, Faculty of Science, Kufa University, Al-Najaf-Iraq.

Abstract

In a continuous attempt to develop novel antibacterial drugs, we have generated and evaluated fresh 1,2,3-triazole derivatives from sulfametoxazole. The synthetic approach was started by the synthesis of sulfametoxazole moiety with alkyl chain or phenyl skeleton. Subsequently, sulfametoxazole nucleus was functionalized with sodium azide to produce 4-azido-N-(5-methylisoxazol-3-yl)benzenesulfonamide. The end 1,2,3-triazoles were synthesized via a click reaction of the azide compound and triple bond derivatives that attached with alkyl chain or phenyl group in good yields. The structures of all prepared compounds were identified by using NMR and IR techniques. The synthesized compounds were screened for their in vitro antibacterial activity against one gram-positive bacteria S. aureus and one gram-negative bacteria E. coli. Among the synthesized compounds, compound 12 was found to be the most potent against staphylococcus aureus with MIC = 20 μg/mL compared with the other prepared compounds. Whereas compound 15 was found to be the most potent against Escherichia coli with MIC = 21 μg/mL compared with the other end compounds. 

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