Synthesis, characterization and biological evaluation of some novel sulfonylurea derivatives

Year 2023, Volume: 27 Issue: 6, 2416 - 2424, 28.06.2025

Fatih Tok , Hümeyra Cihangir Kader Şan Cansel Çakır , Yusuf Sıcak , Mehmet Öztürk , Bedia Kaymakçıoğlu

https://izlik.org/JA46EU66PS

Abstract

In this study, some new sulfonylurea derivatives based on the sulfanilamide compound were synthesized. IR, 1H-NMR, 13C-NMR spectroscopic methods and elemental analysis data were used to confirm the structures of the synthesized compounds. ABTS, DPPH, Cuprac and β-Carotene/linoleic acid assays were performed to evaluate the antioxidant activities of sulphonylurea derivatives. The activities of these compounds against some enzymes (acetylcholinesterase, butrylcholinesterase, tyrosinase, α-amylase and α-glucosidase) were also investigated. Compounds S7, S8, S13 and S14 showed inhibitory activity against α-amylase enzyme with IC50 values of 227.84±1.48-298.27±8.61 µM. In addition, the drug-likeness properties and solubility of the compounds were determined by computational programs.

Keywords

Sulfonylurea , antioxidant , cholinesterase , tyrosinase , α-amylase , α-glucosidase

References

• [1] Wang JG, Lee PKM, Dong YH, Pang SS, Duggleby RG, Li ZM, Guddat LW. Crystal structures of two novel sulfonylurea herbicides in complex with Arabidopsis thaliana acetohydroxyacid synthase. FEBS J. 2009; 276: 1282-1290. https://doi.org/10.1111/j.1742-4658.2009.06863.x
• [2] Leon C, Rodrigues J, Dominguez NG, Charris J, Gut J, Rosenthal PJ, Dominguez JN. Synthesis and evaluation of sulfonylurea derivatives as novel antimalarials. Eur J Med Chem. 2007; 42: 735-742. https://doi.org/10.1016/j.ejmech.2007.01.001
• [3] Wei W, Zhou S, Cheng D, Li Y, Liu J, Xie Y, Li Y, Li Z. Design, synthesis and herbicidal activity study of aryl 2,6-disubstituted sulfonylureas as potent acetohydroxyacid synthase inhibitors. Bioorg Med Chem Lett. 2017; 27: 3365-3369. http://dx.doi.org/10.1016/j.bmcl.2017.06.007
• [4] El-Zahabi MA, Elbendary ER, Bamanie FH, Radwan MF, Ghareib SA, Eissa IH. Design, synthesis, molecular modeling and anti-hyperglycemic evaluation of phthalimide-sulfonylurea hybrids as PPARγ and SUR agonists. Bioorg Chem. 2019; 91: 103115. https://doi.org/10.1016/j.bioorg.2019.103115
• [5] Meng F, Mi P, Yu Z, Wei W, Gao L, Ren J, Li Z, Dai H. Design, synthesis and biological evaluation of 5–substituted sulfonylureas as novel antifungal agents targeting acetohydroxyacid synthase. J Mol Struct. 2022; 1260: 132756. https://doi.org/10.1016/j.molstruc.2022.132756
• [6] Basyouni WM, Abbas SY, El-Bayouki KAM, Younis EA, Ali SA, Aly HF. Synthesis and hyperglycemic, biochemical and histopathological evaluation of novel sulfonylbiguanide and sulfonylurea derivatives as potent anti-diabetic agents. Bioorg Chem. 2021; 117: 105418. https://doi.org/10.1016/j.bioorg.2021.105418
• [7] Sroor FM, Abbas SY, Basyouni WM, El-Bayouki KAM, El-Mansy MF, Aly HF, Ali SA, Arafa AF, Haroun AA. Synthesis, structural characterization and in vivo anti-diabetic evaluation of some new sulfonylurea derivatives in normal and silicate coated nanoparticle forms as anti-hyperglycemic agents. Bioorg Chem. 2019; 92: 103290. https://doi.org/10.1016/j.bioorg.2019.103290
• [8] Idrees D, Hadianawala M, Mahapatra AD, Datta B, Roy S, Ahamad S, Khan P, Hassan MI. Implication of sulfonylurea derivatives as prospective inhibitors of human carbonic anhydrase II. Int J Biol Macromol. 2018; 115: 961-969. https://doi.org/10.1016/j.ijbiomac.2018.04.131
• [9] Ceras J, Cirauqui N, Perez-Silanes S, Aldana I, Monge A, Galiano S. Novel sulfonylurea derivatives as H3 receptor antagonists. Preliminary SAR studies. Eur J Med Chem. 2012; 52: 1-13. https://doi.org/10.1016/j.ejmech.2012.02.049
• [10] Nan X, Jiang YF, Li HJ, Wang JH, Wu YC. Design, synthesis and evaluation of sulfonylurea-containing 4-phenoxyquinolines as highly selective c-Met kinase inhibitors. Biorg Med Chem. 2019; 27: 2801-2812. https://doi.org/10.1016/j.bmc.2019.05.007
• [11] Rostom SAF. Synthesis and in vitro antitumor evaluation of some indeno[1,2-c]-pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores, and some derived thiazole ring systems. Bioorg Med Chem. 2006; 14: 6475-6485. https://doi.org/10.1016/j.bmc.2006.06.020
• [12] Mahapatra AD, Shaik A, Thiruvenkatam V, Datta B. Supramolecular architecture in sulfonylurea, sulfonyldiurea and sulfonyltriurea drugs: Synthesis, X-ray structure and Hirshfeld surface analysis. J Mol Struct. 2021; 1233: 130158. https://doi.org/10.1016/j.molstruc.2021.130158
• [13] Fink C, Sun D, Wagner K, Schneider M, Bauer H, Dolgos H, Mader K, Peters SA. Evaluating the role of solubility in oral absorption of poorly water-soluble drugs using physiologically-based pharmacokinetic modeling. Clin Pharmacol Ther. 2020; 107(3): 650-661. https://doi.org/10.1002/cpt.1672
• [14] Bach P, Boström J, Brickmann K, Giezen JJJ, Groneberg RD, Harvey DM, O’Sullivan M, Zetterberg F. Synthesis, structure–property relationships and pharmacokinetic evaluation of ethyl 6-aminonicotinate sulfonylureas as antagonists of the P2Y12 receptor. Eur J Med Chem. 2013; 65: 360-375. http://dx.doi.org/10.1016/j.ejmech.2013.04.007
• [15] Di L, Fish PV, Mano T. Bridging solubility between drug discovery and development. Drug Discov Today. 2012; 17: 486-496. https://doi.org/10.1016/j.drudis.2011.11.007
• [16] Tok F, Koçyiğit-Kaymakçıoğlu B, İlhan R, Yılmaz S, Ballar-Kırmızıbayrak P, Taşkın-Tok T. Design, synthesis, biological evaluation and molecular docking of novel molecules to PARP-1 enzyme. Turk J Chem. 2019; 43: 1290-1305. https://doi.org/10.3906/kim-1905-15
• [17] Tok F, Baltaş N, Tatar G, Koçyiğit-Kaymakçıoğlu B. Synthesis, Biological Evaluation and in Silico Studies of New Pyrazoline Derivatives Bearing Benzo[d]thiazol-2(3H)-one Moiety as Potential Urease Inhibitors. Chem Biodivers. 2022; 19(3): e202100826. https://doi.org/10.1002/cbdv.202100826
• [18] Liu Y, Chen C, Sun LY, Gao H, Zhen JB, Yang KW. meta-Substituted benzenesulfonamide: a potent scaffold for the development of metallo-β-lactamase ImiS inhibitors. RSC Med Chem. 2020; 11: 259-267. https://doi.org/10.1039/c9md00455f
• [19] Jawale DV, Pratap UR, Rahuja N, Srivastava AK, Mane RA. Synthesis and antihyperglycemic evaluation of new 2,4-thiazolidinediones having biodynamic aryl sulfonylurea moieties. Bioorg Med Chem Lett. 2012; 22: 436-439. https://doi.org/10.1016/j.bmcl.2011.10.110
• [20] Sıcak Y. Design and antiproliferative and antioxidant activities of furan-based thiosemicarbazides and 1,2,4-triazoles: their structure-activity relationship and SwissADME predictions. Med Chem Res. 2021; 30: 1557-1568. https://doi.org/10.1007/s00044-021-02756-z
• [21] Tok F, Çakır C, Çam D, Kırpat MM, Sıcak Y. Synthesis, characterization and biological evaluation of novel thiourea derivatives. Clin Exp Health Sci. 2022; 12: 533-540. https://doi.org/10.33808/clinexphealthsci.1062872
• [22] Bozkurt E, Sıcak Y, Oruç-Emre EE, Karaküçük İyidoğan A, Öztürk M. Design and bioevaluation of novel hydrazide-hydrazones derived from 4-acetyl-N-substituted benzenesulfonamide. Russ J Gen Chem. 2020; 46(5): 702-714. https://doi.org/10.1134/S1068162020050052
• [23] Sıcak Y. Synthesis, predictions of drug-likeness, and pharmacokinetic properties of some chiral thioureas as potent enzyme inhibition agents. Turk J Chem. 2022; 46: 665-676. https://doi.org/10.55730/1300-0527.3358
• [24] Hearing VJ. Methods in enzymology. 142nd ed. New York: Academic Press. 1987; p.154-165.
• [25] Kurşun Aktar BS, Sıcak Y, Tatar G, Oruç-Emre EE. Synthesis, antioxidant and some enzyme inhibition activities of new sulfonyl hydrazones and their molecular docking simulations. Pharm Chem J. 2022; 56(4): 559-569. https://doi.org/10.1007/s11094-022-02674-3
• [26] Quan N, Xuan TD, Tran HD, Thuy NTD, Trang LT, Huong CT, Andriana Y, Tuyen PT. Antioxidant, α-amylase and α-glucosidase inhibitory activities and potential constituents of Canarium tramdenum bark. Molecules. 2019; 24(3): 1-14. https://doi.org/10.3390/molecules24030605
• [27] Kim JS, Kwon CS, Son KH. Inhibition of alpha-glucosidase and amylase by luteolin, a flavonoid. Biosci Biotechnol Biochem. 2000; 64(11): 2458-2461. https://doi.org/10.1271/bbb.64.2458