Synthesis and Antimicrobial and Antioxidant Activities of Sulfonamide Derivatives Containing Tetrazole and Oxadiazole Rings

Abstract

In the present work, we synthesized new sulfonamide derivatives with 1,3,4‐oxadiazole moiety and tetrazole ring. The synthesized derivatives of sulfonamides were characterized through Fourier transform infrared, 13C‐APT‐NMR, 1H‐NMR, and high‐resolution liquid chromatography–mass spectrometry. The biological activities of resulting compound were also investigated and observed that the compounds reveal strong antimicrobial activity over some important bacterial strains including Bacillus subtilis ATCC 6633, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, and Staphylococcus aureus ATCC 29213. The in vitro antifungal properties of synthesized compounds were also a target using Candida albicans NRRL Y‐477 and Saccharomyces cerevisiae fungal strains. We have provided a useful guideline for future studies about the effect of the chemical structures of sulfonamide compounds on the biological activities. Among the target compounds, 7b, 7c, 7d, and 7e demonstrated surprisingly high antimicrobial activities than did others.

Synthesis of Novel Sulfonamide Incorporated Azo Compounds as a PotentSolvatochromic and Antimycobacterial Agents

“…Further, the À CH 3 protons attached to pyran ring in compounds S3 and S4resonated as a singlet at 2.28 ppm and 2.25 ppm respectively. In the proton decoupled 13 CNMR spectra, the carbonyl carbon resonated at 167, 172, 168 and 169 ppm respectively for the compounds S1-S4, the À Me groups attached to pyrimidine ring in compounds S1 and S3 resonated at 27.81 and 28.2 ppm, the -Me groups attached to pyran moiety appeared at δ 14.35 and 13.85 ppm and other peaks are also well agreed with the molecular structure of the compounds.…”

“…Sulfonamides are the important class of drugs found to have antibacterial, [11] insulin‐releasing, [12] carbonic anhydrase inhibitory, [13] anti‐inflammatory, [14] antidiabetic [15] and antitumor activities [16] . Electron‐rich heteroaromatic substrates such as isoxazolone, pyran, pyridine, imidazole, thiophene, thiazole, and benzothiazole are considered as an indisputable, essential feature and part of pharmacophores [17,18] …”

“…[7] In addition to their biological activity evaluation, these are found to have applications in OLEDs, NLO, DSSCs, metal sensing, etc, due to their favourable photophysical characteristics such as solvatochromic absorption and emission, solid state emission, high quantum yield, large stokes shift, etc. [8][9][10] Sulfonamides are the important class of drugs found to have antibacterial, [11] insulin-releasing, [12] carbonic anhydrase inhibitory, [13] anti-inflammatory, [14] antidiabetic [15] and antitumor activities. [16] Electron-rich heteroaromatic substrates such as isoxazolone, pyran, pyridine, imidazole, thiophene, thiazole, and benzothiazole are considered as an indisputable, essential feature and part of pharmacophores.…”

Novel hybrid isoindole‐1,3(2H)‐dione compounds containing a 1H‐tetrazole moiety: Synthesis, biological evaluation, and molecular docking studies

“…[11][12][13][14][15][16] Therefore, these compounds are widely used in many fields, such as chemistry, medicine (Figure 2), [17] the paint and photography industries, and agriculture. [18] Tetrazole chemistry has continued to develop intensively in all directions in recent years. Highly efficient, selective, environmentally friendly methods have been developed for the production and functionalization of the tetrazole ring.…”

Metal-Free Regioselective N2-Arylation of 1H-Tetrazoles with Diaryliodonium Salts

“…Tetrazoles (Tzs) and their N-substituted compounds are highly privileged nitrogen-rich heterocycles owing to their occurrence in several important bio-active compounds (Figure ). In addition to this, the Tz moiety has been found in compounds having applications in material science (photography and military) and agriculture as herbicides . Owing to the presence of a large number of nitrogen atoms in the Tz moiety, it is useful as an environmentally friendly gas generator .…”