Abstract
The aim of this study is to synthesize new benzenesulfonamide derivatives that possess antibacterial activity using Bumetanide as a precursor of benzenesulfonamide. A novel series of hydrazones containing benzenesulfonamides (4a-i) and 1,3,4 oxadiazole containing benzenesulfonamides (5a-e) were prepared and their antibacterial and antifungal activities were measured using microplate broth assay against Gram-positive: Staphylococcus aureus, Gram-negative: Escherichia coli and Pseudomonas aeruginosa and Fungi: Aspergillus fumigates and Candida albicans. The results showed that some of the prepared compounds exhibit a good to excellent activity against the mentioned bacteria, however all the series showed no activity against fungi. Among the series, Compound (4i) demoed an excellent antibacterial activity better than that of the standard reference (Sulfamethoxazole) against Escherichia coli, while compounds (4c, 4e, 4g) showed good activity against all tested bacterial strains equals to Sulfamethoxazole activity. Moreover, compounds (4g, 5d) exert an antimicrobial activity equals to that of Sulfamethoxazole against Pseudomonas aeruginosa, while compounds (4a, 4b, 4c, 4f, 4g, 4h) exhibit similar activity to Sulfamethoxazole against Escherichia coli.
Highlights
The antimicrobial resistance has turned into a menace that confronts the community over the last few decades
The World Health Organization (WHO) stated that though the antimicrobial agents lose their activity, there are insufficient researches that stand up to this catastrophe which means that our competence to overcome the antimicrobial resistance declines dramatically (Gorton et al, 2017)
The starting material of this investigation is Bumetanide; 3-(butylamino)-4-phenoxy-5sulfamoylbenzoic acid (1) which was esterified with methanol in presence of sulfuric acid to afford methyl 3-(butylamino)-4-phenoxy-5sulfamoylbenzoate (2).The ester form (2) underwent hydrazinolysis with hydrazine hydrate in ethanol to yield 3-(butylamino)-5(hydrazinocarbonyl)-2-phenoxybenzenesulfonamide (3) as shown in scheme (1)
Summary
The antimicrobial resistance has turned into a menace that confronts the community over the last few decades. Sci. 2(2), 52- 66, 2018 anticarbonic anhydrase (Saluja et al, 2014; Supuran et al, 2018), diuretics (Fravolini et al., 1991; Al-Kahtani et al, 2016), antiinflammatory (Rodge et al, 2012; Brusco et al., 2015) and anticancer (Ahmed et al, 2015; Alafeefy et al, 2016). Among this class of drugs are sulfa drugs that are the first successfully synthesized antimicrobial agents that exert their action via competitive inhibition of folic acid synthesis, and turn off the microbial nucleic acid replication. Addition of coumarin ring to benzenesulfonamide contributed to the antimicrobial activity of compounds (1, 2) as displayed in figure (1) (Patecl et al, 2010)
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