Synthesis and Biological Evaluation of New 2-Azetidinones with Sulfonamide Structures

Abstract

New series of N-(arylidene)hydrazinoacetyl sulfonamides 4a1–6, 4b1–6 and N-(4-aryl-3-chloro-2-oxoazetidin-1-yl)aminoacetyl sulfonamides 5a1–6, 5b1–6 were synthesized. The structures of the new derivatives was confirmed using spectral methods (FT-IR, 1H-NMR, 13C-NMR). The antibacterial activities of these compounds against Gram positive (Staphyloccoccus aureus ATCC 6583, Staphyloccoccus epidermidis ATCC 12228, Enterococcus faecalis ATCC 25912) and Gram negative (Klebsiella pneumoniae CIP 53153, Proteus vulgaris CIP 104989, Citrobacter freundii CIP 5732, Enterobacter cloacae CIP 103475, Escherichia coli ATCC 25922, Pseudomonas aeruginosa CIP 82118) bacterial strains were evaluated using the broth micro-dilution method. Compound 4a2 displayed the highest antibacterial activity, especially against Staphyloccoccus epidermidis, Enterococcus faecalis and Pseudomonas aeruginosa. The antioxidant potential of the synthesized compounds was also investigated according to ferric reducing power, total antioxidant activity and DPPH radical scavenging assays. All tested compounds showed excellent antioxidant activity in comparison with sulfadiazine and sulfisoxazole which were used as parent sulfonamides. Moreover, some of them showed an antioxidant activity comparable with that of ascorbic acid. In general, the compounds designed based on a sulfadiazine skeleton (compounds 4a1–6, 5a1–6) are more active than those obtained from sulfisoxazole (compounds 4b1–6, 5b1–6), and the N-(arylidene)hydrazinoacetyl sulfonamide derivatives 4a1–6, 4b1–6 are more active than their azetidionone analogues 5a1–6, 5b1–6.

Development and Characterization of Novel Films Based on Sulfonamide-Chitosan Derivatives for Potential Wound Dressing

“…The radical scavenging ability of the chitosan derivatives against 1,1-diphenyl-2-picrylhydrazyl (DPPH) was assessed based on the method described in literature [ 25 , 26 , 27 ] with minor modifications. To 50 µL of stock solution (20 mg/mL in 2% acetic acid) was added 2950 µL of DPPH solution (0.1 nM in methanol).…”

Synthesis, Characterization and Biological Activity of Two New Copper (II) Complexes with N-sulfonamide Ligand

“…The scavenging ability (%) of the complexes was found 69±0.23, for (C1) complexand 80±0.34, for (C2) complex. Comparing the scavenging ability, both complexes are less active than ascorbic acid (97.08±0.52) [50] [51].…”

Synthesis, Characterization, and Evaluation of in vitro Antidiabetic Activity of Novel Pyrrolidine Sulphonamide Derivative

“…Its pharmacokinetic studies have shown that it is suitable for once-a-week dosing, which makes it unique among the other DPP-4 inhibitors. 18,19 In this research we have designed novel 1,2,4-oxadiazole derivatives with sulfonamide and pyrrolidine-2-carbonitrile scaffolds specifically in vitro DPP-IV inhibitor assay as antidiabetic activity. In the continuation of our research to develop small molecules as biologically active antihyperglycaemic compounds, new derivatives having a pyrrolidine-2-carbonitrile-sulfonamide backbone hybrid were designed and synthesized in search for new potent DPP-4 inhibitors as antidiabetic agents.…”