TY - JOUR AU - Uzun, Demet AU - Erdoğdu, Ebru AU - Balaban Gündüzalp, Ayla AU - Özmen Özdemir, Ümmühan AU - Öztürk, Ali AU - Özbek, Neslihan AU - Kaya, Kerem AU - Abdulmajet, Olkar PY - 2021/12/08 Y2 - 2024/03/29 TI - New sulfonylhydrazones containing methane sulfonic acid hydrazıde havıng human anticarbonic anhydrase and antimicrobıal activıty: synthesis, spectroscopic characterization, electrochemical properties, and biological activıties JF - Macedonian Journal of Chemistry and Chemical Engineering JA - Maced. J. Chem. Chem. Eng. VL - 40 IS - 2 SE - Organic Chemistry DO - 10.20450/mjcce.2021.2416 UR - https://mjcce.org.mk/index.php/MJCCE/article/view/2416 SP - 181-196 AB - <p>In this work, new sulfonylhydrazones nomenclatured as 3,5-ditertbutylsalicylaldehyde methane­sulfonylhydrazone (<strong>II</strong>), 3-tertbutylsalicylaldehyde methanesulfonylhydrazone (<strong>III</strong>), and 5-bromosalicyl­aldehyde methanesulfonylhydrazone (<strong>IV</strong>) were synthesized by the reaction of methanesulfo­nicacidhydrazide (<strong>I</strong>) with 3,5-ditertbutylsalicylaldehyde, 3-tertbutylsalicyl aldehyde, and 5-bromosalicylaldehyde. The structures of the aromatic sulfonylhydrazones were determined by using elemental analysis, UV-Vis, FT-IR, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR methods. The structure of <strong>IV</strong> was also supported with the X-ray diffraction method. Sulfonamides were generally investigated for their inhibitory effects on human carbonic anhydrase isoenzymes (hCAs). Synthesized alkyl­sulfonylhydrazones have a sulfonamide group, which is the most important pharmacophore for the carbonic anhydrase (CA) inhibition efficiency like the reference agent acetazolamide (AAZ). The enzyme inhibition trends of alkylsulfonylhydrazones on the hCA I isoenzyme were qualitatively investigated by cyclic voltammetry (CV) and differantial pulse voltammetry (DPV). Also, the inhibition activities of sulfonylhydrazones were determined by using UV-Vis spectrophotometry, and their inhibition parameters, such as <em>K</em><sub>m</sub>, IC<sub>50</sub>, and <em>K</em><sub>i</sub>, were calculated. Among the tested compounds, <strong>IV</strong> was found to be the most active compound on the hCA I isoenzyme with an IC<sub>50</sub> value of 4.86×10<sup>–6</sup> M, whereas <strong>II</strong> and <strong>III</strong> were found to be the least potent compounds on hCA I with an IC<sub>50</sub> value of 3.96×10<sup>–4</sup> M and 5.58×10<sup>–5</sup> M, respectively.</p>All of the compounds showed excellent inhibition activity against gram-negative bacteria (<em>Escherichia coli</em>, <em>Klebsiella pneumoniae</em>, <em>Pseudomonas aeruginosa,</em> <em>Stenotrophomonas maltophilia</em>) and gram-positive bacteria (<em>Staphylococcus aureus</em>, <em>Staphylococcus epidermidi</em>), with minimum inhibitory concentration (MIC) values less than that of standard drugs (sulfamethoxazole and sulfisoxazole). In addition, all of the compounds exhibited excellent antifungal inhibition against <em>C. albicans</em> and <em>A. fumigatus</em>, with MIC values of 8–16 μg/ml, which were 2–4 fold higher than the standard drug fluconazole (32 μg/ml). ER -