Carbonic anhydrase inhibitors: Synthesis, characterization and inhibition activities of furan sulfonylhydrazones against carbonic anhydrase I (hCA I)

• Published in: Journal of molecular structure 2016-02, Vol.1105, p.332-340
• Main Authors: Gündüzalp, Ayla Balaban, Parlakgümüş, Gökhan, Uzun, Demet, Özmen, Ümmuhan Özdemir, Özbek, Neslihan, Sarı, Musa, Tunç, Tuncay
• Format: Article
• Language: English
• Subjects: Carbonic anhydrase I (hCA I); Cyclic voltammetry (CV); Differantial pulse voltammetry (DPV); Enzyme inhibition; Furan sulfonylhydrazone
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2015.10.054

The methane sulfonic acide hydrazide (1) was used to obtain furan sulfonylhydrazones; 2-acetylfuranmethanesulfonylhydrazone (2), 2-furaldehydemethanesulfonylhydrazone (3), 5-nitro-2-furaldehydemethanesulfonylhydrazone (4). The structures of furan sulfonylhydrazones were determined by using elemental analysis, FT-IR, 1H NMR, 13C NMR and UV–vis methods. The structure of 5-nitro-2-furaldehydemethanesulfonylhydrazone (4) was also supported with X-ray difraction method and found that compound 4 was crystallized in triclinic, space group P1¯. In order to gain insight into the structure of the compounds, we performed computational studies by using 6–311G(d,p) basic set in which B3LYP correlation function was implemented. The geometry of the sulfonylhydrazones were optimized at DFT method with Gaussian 09 program package and the global reactivity descriptors were also calculated by this basic set. The enzyme inhibition activities of the sulfonylhydrazones were investigated on carbonic anhydrase I (hCA I) isoenzyme and their activity parameters (Km, IC50 and Ki) were calculated by spectrophotometric method. And also, their inhibitor effects were also investigated by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods. Inhibition results show that compound 4 containing electron withdrawing group (NO2) has higher inhibition effect on hCA I isoenzyme than other's. The furan sulfonylhydrazones were characterized by using elemental analysis, 1H–13C NMR, IR and UV–vis spectrum. The carbonic anhydrase I (hCA I) inhibition effects of compounds were determined by spectrophotometric and electrochemical methods. [Display omitted] •Furan sulfonylhydrazones were synthesized and characterized.•hCA I activities were studied by spectrophotometric and electrochemical methods.•The electroactivity of compounds were determined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods.