New N-(1,3,4-thiadiazole-2-yl)acetamide derivatives as human carbonic anhydrase I and II and acetylcholinesterase inhibitors

References

• Abas, M., Bahadur, A., Ashraf, Z., Iqbal, S., Rajoka, M. S. R., Rashid, S. G., Jabeen, E., Iqbal, Z., Abbas, Q., Bais, A., Hassan, M., Liu, G., Feng, K., Lee, S. H., Nawaz, M., & Qayyum, M. A. (2021). Designing novel anticancer sulfonamide based 2, 5-disubstituted-1, 3, 4-thiadiazole derivatives as potential carbonic anhydrase inhibitor. Journal of Molecular Structure, 1246, 131145. https://doi.org/10.1016/j.molstruc.2021.131145
   Web of Science ®Google Scholar
• Abdel-Hamid, M. K., Abdel-Hafez, A. A., El-Koussi, N. A., Mahfouz, N. M., Innocenti, A., & Supuran, C. T. (2007). Design, synthesis, and docking studies of new 1, 3, 4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity. Bioorganic & Medicinal Chemistry, 15(22), 6975–6984. https://doi.org/10.1016/j.bmc.2007.07.044
   PubMed Web of Science ®Google Scholar
• Acar Çevik, U., Işık, A., Evren, A., Kapusız, Ö., Gül, Ü., Özkay, Y., & Kaplancıklı, Z. (2022). Synthesis of new benzimidazole derivatives containing 1, 3, 4-thiadiazole: Their in vitro antimicrobial, in silico molecular docking and molecular dynamic simulations studies. SAR and QSAR in Environmental Research, 33(11), 899–914. https://doi.org/10.1080/1062936X.2022.2149620
   PubMed Web of Science ®Google Scholar
• Alterio, V., Di Fiore, A., D'Ambrosio, K., Supuran, C. T., & De Simone, G. (2012). Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms? Chemical Reviews, 112(8), 4421–4468. https://doi.org/10.1021/cr200176r
   PubMed Web of Science ®Google Scholar
• Aouad, M. R., Almehmadi, M. A., Albelwi, F. F., Teleb, M., Tageldin, G. N., Abu-Serie, M. M., Hagar, M., & Rezki, N. (2022). Targeting the interplay between MMP-2, CA II and VEGFR-2 via new sulfonamide-tethered isomeric triazole hybrids; Microwave-assisted synthesis, computational studies and evaluation. Bioorganic Chemistry, 124, 105816. https://doi.org/10.1016/j.bioorg.2022.105816
   PubMed Web of Science ®Google Scholar
• Askin, S., Tahtaci, H., Türkeş, C., Demir, Y., Ece, A., Çiftçi, G. A., & Beydemir, Ş. (2021). Design, synthesis, characterization, in vitro and in silico evaluation of novel imidazo [2, 1-b][1, 3, 4] thiadiazoles as highly potent acetylcholinesterase and non-classical carbonic anhydrase inhibitors. Bioorganic Chemistry, 113, 105009. https://doi.org/10.1016/j.bioorg.2021.105009
   PubMed Web of Science ®Google Scholar
• Asseri, A. H., Alam, M. J., Alzahrani, F., Khames, A., Pathan, M. T., Abourehab, M. A. S., Hosawi, S., Ahmed, R., Sultana, S. A., Alam, N. F., Alam, N.-U., Alam, R., Samad, A., Pokhrel, S., Kim, J. K., Ahammad, F., Kim, B., & Tan, S. C. (2022). Toward the identification of natural antiviral drug candidates against merkel cell polyomavirus: Computational drug design approaches. Pharmaceuticals, 15(5), 501. https://doi.org/10.3390/ph15050501
   Web of Science ®Google Scholar
• Atmaram, U. A., & Roopan, S. M. (2022). Biological activity of oxadiazole and thiadiazole derivatives. Applied Microbiology and Biotechnology, 106(9–10), 3489–3505. https://doi.org/10.1007/s00253-022-11969-0
   PubMed Web of Science ®Google Scholar
• Bassani, D., Pavan, M., Bolcato, G., Sturlese, M., & Moro, S. (2022). Re-exploring the ability of common docking programs to correctly reproduce the binding modes of non-covalent inhibitors of SARS-CoV-2 protease MPRO. Pharmaceuticals, 15(2), 180. https://doi.org/10.3390/ph15020180
   Web of Science ®Google Scholar
• Becke, A. D. (1992). Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction. The Journal of Chemical Physics, 96(3), 2155–2160. https://doi.org/10.1063/1.462066
   Web of Science ®Google Scholar
• Bulos, J. A., Guo, R., Wang, Z., DeLessio, M. A., Saven, J. G., & Dmochowski, I. J. (2021). Design of a superpositively charged enzyme: Human carbonic anhydrase II variant with ferritin encapsulation and immobilization. Biochemistry, 60(47), 3596–3609. https://doi.org/10.1021/acs.biochem.1c00515
   PubMed Web of Science ®Google Scholar
• Chen, A. Y., Adamek, R. N., Dick, B. L., Credille, C. V., Morrison, C. N., & Cohen, S. M. (2018). Targeting metalloenzymes for therapeutic intervention. Chemical Reviews, 119(2), 1323–1455. https://doi.org/10.1021/acs.chemrev.8b00201
   PubMed Web of Science ®Google Scholar
• Coşkun, G., Birgül, K., Evren, A. E., Küçükgüzel, ŞG., & Ülgen, M. (2023). In Silico studies and in vitro microsomal metabolism of potent MetAP2 inhibitor and in vivo tumor suppressor for prostate cancer: A thioether-triazole hybrid. Acıbadem Üniversitesi Sağlık Bilimleri Dergisi, 14(1), 10–23. https://doi.org/10.31067/acusaglik.1210129
   Google Scholar
• Dawbaa, S., Evren, A. E., Sağlik, B. N., Gundogdu-Karaburun, N., & Karaburun, A. C. (2022). Biological activity evaluation of novel monoamine oxidase inhibitory compounds targeting Parkinson disease. Future Medicinal Chemistry, 14(22), 1663–1679. https://doi.org/10.4155/fmc-2022-0167
   PubMed Web of Science ®Google Scholar
• Dennington, R., Keith, T., & Millam, J. (2009). GaussView, version 5. Shawnee Mission: Semichem Inc.
   Google Scholar
• Di Fiore, A., De Luca, V., Langella, E., Nocentini, A., Buonanno, M., Monti, S. M., Supuran, C. T., Capasso, C., & De Simone, G. (2022). Biochemical, structural, and computational studies of a γ-carbonic anhydrase from the pathogenic bacterium Burkholderia pseudomallei. Computational and Structural Biotechnology Journal, 20, 4185–4194. https://doi.org/10.1016/j.csbj.2022.07.033
   PubMed Web of Science ®Google Scholar
• Dokmanić, I., Sikić, M., & Tomić, S. (2008). Metals in proteins: Correlation between the metal-ion type, coordination number and the amino-acid residues involved in the coordination. Acta Crystallographica Section D, Biological Crystallography, 64(Pt 3), 257–263. https://doi.org/10.1107/S090744490706595X
   PubMedGoogle Scholar
• Dvir, H., Silman, I., Harel, M., Rosenberry, T. L., & Sussman, J. L. (2010). Acetylcholinesterase: From 3D structure to function. Chemico-Biological Interactions, 187(1–3), 10–22. https://doi.org/10.1016/j.cbi.2010.01.042
   PubMed Web of Science ®Google Scholar
• Ekins, S., Mestres, J., & Testa, B. (2007). In silico pharmacology for drug discovery: Methods for virtual ligand screening and profiling. British Journal of Pharmacology, 152(1), 9–20. https://doi.org/10.1038/sj.bjp.0707305
   PubMed Web of Science ®Google Scholar
• Ellman, G. L., Courtney, K. D., Andres, V., & Feather-Stone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88–95. https://doi.org/10.1016/0006-2952(61)90145-9
   PubMed Web of Science ®Google Scholar
• Ergena, A., Rajeshwar, Y., & Solomon, G. (2022). Synthesis and diuretic activity of substituted 1, 3, 4-thiadiazoles. Scientifica, 2022, 3011531–3011539. https://doi.org/10.1155/2022/3011531
   PubMed Web of Science ®Google Scholar
• Evren, A. E., Demokrat, N., & Yurttaş, L. (2022). Focusing on the moderately active compound (MAC) in the design and development of strategies to optimize the apoptotic effect by molecular mechanics techniques. European Journal of Life Sciences, 1(3), 118–126. https://doi.org/10.55971/EJLS.1209591
   Google Scholar
• Evren, A. E., Karaduman, A. B., Sağlik, B. N., Özkay, Y., & Yurttaş, L. (2022). Investigation of novel quinoline–thiazole derivatives as antimicrobial agents: In Vitro and in silico approaches. ACS Omega, 8(1), 1410–1429. https://doi.org/10.1021/acsomega.2c06871
   PubMed Web of Science ®Google Scholar
• Evren, A. E., Nuha, D., Dawbaa, S., Sağlık, B. N., & Yurttaş, L. (2022). Synthesis of novel thiazolyl hydrazone derivatives as potent dual monoamine oxidase-aromatase inhibitors. European Journal of Medicinal Chemistry, 229, 114097. https://doi.org/10.1016/j.ejmech.2021.114097
   PubMed Web of Science ®Google Scholar
• Fu, X., Li, S., Jing, F., Wang, X., Li, B., Zhao, J., Liu, Y., & Chen, B. (2016). Synthesis and biological evaluation of novel 1, 3, 4-thiadiazole derivatives incorporating benzisoselenazolone scaffold as potential antitumor agents. Medicinal Chemistry, 12(7), 631–639. https://doi.org/10.2174/1573406412666160201120806
   PubMed Web of Science ®Google Scholar
• Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science, 218(4574), 747–754. https://doi.org/10.1126/science.218.4574.747
   PubMed Web of Science ®Google Scholar
• Gaussian09, R. A. (2009). 1, mj frisch, gw trucks, hb schlegel, ge scuseria, ma robb, jr cheeseman, g. Scalmani, v. Barone, b. Mennucci, ga petersson et al (Vol. 121, pp. 150–166). Gaussian. Inc.
   Google Scholar
• Gowda, K., Swarup, H. A., Nagarakere, S. C., Rangappa, S., Kanchugarkoppal, R. S., & Kempegowda, M. (2020). Structural studies of 2, 5-disubstituted 1, 3, 4-thiadiazole derivatives from dithioesters under the mild condition: Studies on antioxidant, antimicrobial activities, and molecular docking. Synthetic Communications, 50(10), 1528–1544. https://doi.org/10.1080/00397911.2020.1745843
   Web of Science ®Google Scholar
• Gregory, D. S., Martin, A. C., Cheetham, J. C., & Rees, A. R. (1993). The prediction and characterization of metal binding sites in proteins. Protein Engineering, 6(1), 29–35. https://doi.org/10.1093/protein/6.1.29
   PubMedGoogle Scholar
• Güleç, Ö., Türkeş, C., Arslan, M., Demir, Y., Yeni, Y., Hacımüftüoğlu, A., Ereminsoy, E., Küfrevioğlu, Ö. İ., & Beydemir, Ş. Ş (2022). Cytotoxic effect, enzyme inhibition, and in silico studies of some novel N-substituted sulfonyl amides incorporating 1, 3, 4-oxadiazol structural motif. Molecular Diversity, 26(5), 2825–2845. https://doi.org/10.1007/s11030-022-10422-8
   PubMed Web of Science ®Google Scholar
• Güzel-Akdemir, Ö., Akdemir, A., Karalı, N., & Supuran, C. T. (2015). Discovery of novel isatin-based sulfonamides with potent and selective inhibition of the tumor-associated carbonic anhydrase isoforms IX and XII. Organic & Biomolecular Chemistry, 13(23), 6493–6499. https://doi.org/10.1039/c5ob00688k
   PubMed Web of Science ®Google Scholar
• Güzel, E., Acar Çevik, U., Evren, A. E., Bostancı, H. E., Gül, Ü. D., Kayış, U., Özkay, Y., & Kaplancıklı, Z. A. (2023). Synthesis of benzimidazole-1, 2, 4-triazole derivatives as potential antifungal agents targeting 14α-demethylase. ACS Omega, 8(4), 4369–4384. https://doi.org/10.1021/acsomega.2c07755
   PubMed Web of Science ®Google Scholar
• Jatczak, M., Muylaert, K., De Coen, L. M., Keemink, J., Wuyts, B., Augustijns, P., & Stevens, C. V. (2014). Straightforward entry to pyrido [2, 3-d] pyrimidine-2, 4 (1H, 3H)-diones and their ADME properties. Bioorganic & Medicinal Chemistry, 22(15), 3947–3956. https://doi.org/10.1016/j.bmc.2014.06.009
   PubMed Web of Science ®Google Scholar
• Kakakhan, C., Türkeş, C., Güleç, Ö., Demir, Y., Arslan, M., Özkemahlı, G., & Beydemir, Ş. Ş (2023). Exploration of 1, 2, 3-triazole linked benzenesulfonamide derivatives as isoform selective inhibitors of human carbonic anhydrase. Bioorganic & Medicinal Chemistry, 77, 117111. https://doi.org/10.1016/j.bmc.2022.117111
   PubMed Web of Science ®Google Scholar
• Kalinin, S., Kovalenko, A., Valtari, A., Nocentini, A., Gureev, M., Urtti, A., Korsakov, M., Supuran, C. T., & Krasavin, M. (2022). 5-(Sulfamoyl) thien-2-yl 1, 3-oxazole inhibitors of carbonic anhydrase II with hydrophilic periphery. Journal of Enzyme Inhibition and Medicinal Chemistry, 37(1), 1005–1011. https://doi.org/10.1080/14756366.2022.2056733
   PubMed Web of Science ®Google Scholar
• Karaburun, A. Ç., Acar Çevik, U., Osmaniye, D., Sağlık, B. N., Kaya Çavuşoğlu, B., Levent, S., Özkay, Y., Koparal, A. S., Behçet, M., & Kaplancıklı, Z. A. (2018). Synthesis and evaluation of new 1, 3, 4-thiadiazole derivatives as potent antifungal agents. Molecules (Basel, Switzerland), 23(12), 3129. https://doi.org/10.3390/molecules23123129
   PubMed Web of Science ®Google Scholar
• Kasımoğulları, R., Bülbül, M., Arslan, B. S., & Gökçe, B. (2010). Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1, 3, 4-thiadiazole-2-sulfonamide. European Journal of Medicinal Chemistry, 45(11), 4769–4773. https://doi.org/10.1016/j.ejmech.2010.07.041
   PubMed Web of Science ®Google Scholar
• Khan, F. A. K., Patil, R. H., Shinde, D. B., & Sangshetti, J. N. (2016). Bacterial Peptide deformylase inhibition of cyano substituted biaryl analogs: Synthesis, in vitro biological evaluation, molecular docking study and in silico ADME prediction. Bioorganic & Medicinal Chemistry, 24(16), 3456–3463. https://doi.org/10.1016/j.bmc.2016.05.051
   PubMed Web of Science ®Google Scholar
• Lolak, N., Akocak, S., Durgun, M., Duran, H. E., Necip, A., Türkeş, C., Işık, M., & Beydemir, Ş. (2022). Novel bis-ureido-substituted sulfaguanidines and sulfisoxazoles as carbonic anhydrase and acetylcholinesterase inhibitors. Molecular Diversity, 27(4), 1735–1749. https://doi.org/10.1007/s11030-022-10527-0
   PubMed Web of Science ®Google Scholar
• Long, D. D., Frieman, B., Hegde, S. S., Hill, C. M., Jiang, L., Kintz, S., Marquess, D. G., Purkey, H., Shaw, J.-P., Steinfeld, T., Wilson, M. S., & Wrench, K. (2013). A multivalent approach towards linked dual-pharmacology prostaglandin F receptor agonist/carbonic anhydrase-II inhibitors for the treatment of glaucoma. Bioorganic & Medicinal Chemistry Letters, 23(4), 939–943. https://doi.org/10.1016/j.bmcl.2012.12.058
   PubMed Web of Science ®Google Scholar
• Lotfi, S., Rahmani, T., Hatami, M., Pouramiri, B., Kermani, E. T., Rezvannejad, E., Mortazavi, M., Fathi Hafshejani, S., Askari, N., Pourjamali, N., & Zahedifar, M. (2020). Design, synthesis and biological assessment of acridine derivatives containing 1, 3, 4-thiadiazole moiety as novel selective acetylcholinesterase inhibitors. Bioorganic Chemistry, 105, 104457. https://doi.org/10.1016/j.bioorg.2020.104457
   PubMed Web of Science ®Google Scholar
• Luque, F., Orozco, M., Bhadane, P., & Gadre, S. (1993). SCRF calculation of the effect of water on the topology of the molecular electrostatic potential. The Journal of Physical Chemistry, 97(37), 9380–9384. https://doi.org/10.1021/j100139a021
   Web of Science ®Google Scholar
• Nocentini, A., Supuran, C. T., & Capasso, C. (2021). An overview on the recently discovered iota-carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry, 36(1), 1988–1995. https://doi.org/10.1080/14756366.2021.1972995
   PubMed Web of Science ®Google Scholar
• Osmaniye, D., Evren, A. E., Sağlık, B. N., Levent, S., Özkay, Y., & Kaplancıklı, Z. A. (2022). Design, synthesis, biological activity, molecular docking, and molecular dynamics of novel benzimidazole derivatives as potential AChE/MAO‐B dual inhibitors. Archiv Der Pharmazie, 355(3), e2100450. https://doi.org/10.1002/ardp.202100450
   PubMed Web of Science ®Google Scholar
• Osmaniye, D., Türkeş, C., Demir, Y., Özkay, Y., Beydemir, Ş., & Kaplancıklı, Z. A. (2022). Design, synthesis, and biological activity of novel dithiocarbamate‐methylsulfonyl hybrids as carbonic anhydrase inhibitors. Archiv Der Pharmazie, 355(8), e2200132. https://doi.org/10.1002/ardp.202200132
   PubMed Web of Science ®Google Scholar
• Pagnozzi, D., Pala, N., Biosa, G., Dallocchio, R., Dessì, A., Singh, P. K., Rogolino, D., Di Fiore, A., De Simone, G., Supuran, C. T., & Sechi, M. (2022). Interaction studies between carbonic anhydrase and a sulfonamide inhibitor by experimental and theoretical approaches. ACS Medicinal Chemistry Letters, 13(2), 271–277. https://doi.org/10.1021/acsmedchemlett.1c00644
   Web of Science ®Google Scholar
• Politzer, P., & Murray, J. S. (2002). The fundamental nature and role of the electrostatic potential in atoms and molecules. Theoretical Chemistry Accounts, 108(3), 134–142. https://doi.org/10.1007/s00214-002-0363-9
   Web of Science ®Google Scholar
• Rocca, R., Scionti, F., Nadai, M., Moraca, F., Maruca, A., Costa, G., Catalano, R., Juli, G., Di Martino, M. T., Ortuso, F., Alcaro, S., Tagliaferri, P., Tassone, P., Richter, S. N., & Artese, A. (2022). Chromene derivatives as selective TERRA G-quadruplex RNA binders with antiproliferative properties. Pharmaceuticals, 15(5), 548. https://doi.org/10.3390/ph15050548
   Web of Science ®Google Scholar
• Schrödinger Release. (2020a). Schrödinger release 2020–3, desmond. Schrödinger, LLC.
   Google Scholar
• Schrödinger Release. (2020b). Schrödinger Release 2020–3, glide. Schrödinger, LLC.
   Google Scholar
• Schrödinger Release. (2020c). Schrödinger release. 2020–3: LigPrep 2020. Schrödinger, LLC.
   Google Scholar
• Skrzypek, A., Matysiak, J., Karpińska, M., Czarnecka, K., Kręcisz, P., Stary, D., Kukułowicz, J., Paw, B., Bajda, M., Szymański, P., & Niewiadomy, A. (2021). Biological evaluation and molecular docking of novel 1, 3, 4-thiadiazole-resorcinol conjugates as multifunctional cholinesterases inhibitors. Bioorganic Chemistry, 107, 104617. https://doi.org/10.1016/j.bioorg.2020.104617
   PubMed Web of Science ®Google Scholar
• Supuran, C. T., & Clare, B. W. (1999). Carbonic anhydrase inhibitors–Part 57: Quantum chemical QSAR of a group of 1, 3, 4-thiadiazole-and 1, 3, 4-thiadiazoline disulfonamides with carbonic anhydrase inhibitory properties. European Journal of Medicinal Chemistry, 34(1), 41–50. https://doi.org/10.1016/S0223-5234(99)80039-7
   Web of Science ®Google Scholar
• Supuran, C. T., & Scozzafava, A. (2000a). Carbonic anhydrase inhibitors-Part 94. 1, 3, 4-Thiadiazole-2-sulfonamide derivatives as antitumor agents? European Journal of Medicinal Chemistry, 35(9), 867–874. https://doi.org/10.1016/s0223-5234(00)00169-0
   PubMed Web of Science ®Google Scholar
• Supuran, C. T., & Scozzafava, A. (2000b). Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opinion on Therapeutic Patents, 10(5), 575–600. https://doi.org/10.1517/13543776.10.5.575
   Web of Science ®Google Scholar
• Taraphder, S., Maupin, C. M., Swanson, J. M., & Voth, G. A. (2016). Coupling protein dynamics with proton transport in human carbonic anhydrase II. The Journal of Physical Chemistry. B, 120(33), 8389–8404. https://doi.org/10.1021/acs.jpcb.6b02166
   PubMed Web of Science ®Google Scholar
• Thiry, A., Supuran, C. T., Masereel, B., & Dogné, J. M. (2008). Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. Journal of Medicinal Chemistry, 51(11), 3051–3056. https://doi.org/10.1021/jm701526d
   PubMed Web of Science ®Google Scholar
• Turan Yücel, N., Evren, A. E., Kandemir, Ü., & Can, Ö. D. (2022). Antidepressant-like effect of tofisopam in mice: A behavioural, molecular docking and MD simulation study. Journal of Psychopharmacology (Oxford, England), 36(7), 819–835. https://doi.org/10.1177/02698811221095528
   PubMed Web of Science ®Google Scholar
• Türkeş, C., Akocak, S., Işık, M., Lolak, N., Taslimi, P., Durgun, M., Gülçin, İ., Budak, Y., & Beydemir, Ş. (2022). Novel inhibitors with sulfamethazine backbone: Synthesis and biological study of multi-target cholinesterases and α-glucosidase inhibitors. Journal of Biomolecular Structure & Dynamics, 40(19), 8752–8764. https://doi.org/10.1080/07391102.2021.1916599
   PubMed Web of Science ®Google Scholar
• Türkeş, C., Demir, Y., & Beydemir, Ş. Ş (2021). Calcium channel blockers: Molecular docking and inhibition studies on carbonic anhydrase I and II isoenzymes. Journal of Biomolecular Structure & Dynamics, 39(5), 1672–1680. https://doi.org/10.1080/07391102.2020.1736631
   PubMed Web of Science ®Google Scholar
• Verpoorte, J. A., Mehta, S., & Edsall, J. T. (1967). Esterase activities of human carbonic anhydrases B and C. Journal of Biological Chemistry, 242(18), 4221–4229. https://doi.org/10.1016/S0021-9258(18)95800-X
   PubMed Web of Science ®Google Scholar
• Wu, Z., Shi, J., Chen, J., Hu, D., & Song, B. (2021). Design, synthesis, antibacterial activity, and mechanisms of novel 1, 3, 4-thiadiazole derivatives containing an amide moiety. Journal of Agricultural and Food Chemistry, 69(31), 8660–8670. https://doi.org/10.1021/acs.jafc.1c01626
   PubMed Web of Science ®Google Scholar
• Yang, Y., Hu, X. Q., Li, Q. S., Zhang, X. X., Ruan, B. F., Xu, J., & Liao, C. (2016). Metalloprotein inhibitors for the treatment of human diseases. Current Topics in Medicinal Chemistry, 16(4), 384–396. https://doi.org/10.2174/1568026615666150813145218
   PubMed Web of Science ®Google Scholar