Discovery of potent carbonic anhydrase, acetylcholinesterase, and butyrylcholinesterase enzymes inhibitors: The new amides and thiazolidine-4-ones synthesized on an acetophenone base
Parham Taslimi
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorSabiya Osmanova
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorCorresponding Author
İlhami Gulçin
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia
Correspondence
Ilhami Gulcin
E-mails: [email protected], [email protected]
Search for more papers by this authorSabira Sardarova
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorVagif Farzaliyev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorAfsun Sujayev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorRuya Kaya
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorFatma Koc
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorSukru Beydemir
Department of Biochemistry, Faculty of Pharmacy, Anadolu University, Eskişehir, 26470 Turkey
Search for more papers by this authorSaleh H. Alwasel
Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia
Search for more papers by this authorOmer Irfan Kufrevioglu
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorParham Taslimi
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorSabiya Osmanova
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorCorresponding Author
İlhami Gulçin
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia
Correspondence
Ilhami Gulcin
E-mails: [email protected], [email protected]
Search for more papers by this authorSabira Sardarova
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorVagif Farzaliyev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorAfsun Sujayev
Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences, Baku, 1029 Azerbaijan
Search for more papers by this authorRuya Kaya
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorFatma Koc
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorSukru Beydemir
Department of Biochemistry, Faculty of Pharmacy, Anadolu University, Eskişehir, 26470 Turkey
Search for more papers by this authorSaleh H. Alwasel
Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia
Search for more papers by this authorOmer Irfan Kufrevioglu
Department of Chemistry, Faculty of Sciences, Ataturk University, Erzurum, 25240 Turkey
Search for more papers by this authorAbstract
Compounds containing nitrogen and sulfur atoms can be widely used in various fields, including industry, medicine, biotechnology, and chemical technology. Among them, amides of acids and heterocyclic compounds have an important place. These amides and thiazolidine-4-ones showed good inhibitory action against butyrylcholinesterase (BChE), acetylcholinesterase (AChE), and human carbonic anhydrase isoforms. AChE exists at high concentrations in the brain and red blood cells. BChE is an important enzyme that is plentiful in the liver, and it is released into the blood in a soluble form. They were demonstrated to have effective inhibition profiles with Ki values of 23.76–102.75 nM against hCA I, 58.92–136.64 nM against hCA II, 1.40–12.86 nM against AChE, and 9.82–52.77 nM against BChE. On the other hand, acetazolamide showed Ki value of 482.63 ± 56.20 nM against hCA I, and 1019.60 ± 163.70 nM against hCA II. Additionally, Tacrine inhibited AChE and BChE, showing Ki values of 397.03 ± 31.66 and 210.21 ± 15.98 nM, respectively.
REFERENCES
- 1P. Series, Chichester. 2007, 2, 13.
- 2V. I. Iwanski, Higher School. 1978, 559.
- 3S. P. Singh, S. D. Parmar, K. Raman, Chem. Rev. 1981, 81, 175–203.
- 4C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405–3415.
- 5P. S. Chaudhari, S. D. Salim, R. V. Sawant, K. G. Akamanchi, Green Chem. 2010, 12, 1707–1710.
- 6K. Komura, Y. Nakano, M. Koketsu, Green Chem. 2011, 13, 828–831.
- 7V. M. Mokhov, Y. V. Popov, News VSTU 2014, 134, 52–56.
- 8S. F. Osmanov, S. A. Sardarova, F. A. Mamedov, Int. Cong. Heterocycl. Chem. 2015, p 493.
- 9A. Solankee, K. Kapadia, P. Mistry, J. Patel, Oriental J. Chem. 1999, 15, 303–319.
- 10W. Cunico, C. R. B. Gomes, M. D. L. G. Ferreira, L. R. Capri, M. Soares, S. M. S. V. Wardell, Tetrahedron Lett. 2007, 48, 6217–6220.
- 11S. F. Osmanov, S. A. Sardarova, F. A. Mamedov, Heterocycl. Chem. 2015, 493, 18–23.
- 12C. T. Supuran, A. Scozzafava, Bioorg. Med. Chem. 2007, 15, 4336–4350.
- 13A. Bertucci, A. Moya, S. Tambutté, D. Allemand, C. T. Supuran, D. Zoccola, Bioorg. Med. Chem. 2013, 21, 1437–1450.
- 14N. K. Tafreshi, M. C. Lloyd, M. M. Bui, R. J. Gillies, D. L. Morse, Subcell Biochem. 2014, 75, 221–254.
- 15C. L. Lomelino, C. T. Supuran, R. McKenna. Int. J. Mol. Sci. 2016, 17, 1150.
- 16E. Hanf, A. Böhmer, M. Zinke, S. Gambaryan, A. Schwarz, C. T. Supuran, D. Tsikas, Amino Acids 2016, 48, 1695–1706.
- 17A. Scozzafava, P. Kalın, C. T. Supuran, I. Gülçin, S. Alwasel, J. Enzyme Inhib. Med. Chem. 2015, 30, 941–946.
- 18E. Garibov, P. Taslimi, A. Sujayev, Z. Bingöl, S. Çetinkaya, I. Gulcin, S. Beydemir, V. Farzaliyev, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31(S3), 1–9.
- 19C. T. Supuran, Curr. Pharm. Des. 2010, 16, 3233–3245.
- 20Z. Huyut, S. Beydemir, İ. Gulcin, J. Enzyme Inhib. Med. Chem. 2016, 31, 1199–205.
- 21A. Scozzafava, M. Passaponti, C. T. Supuran, I. Gulçin, J. Enzyme Inhib. Med. Chem. 2015, 30, 586–591. 25.
- 22B. Arabaci, I. Gülçin, S. Alwasel, Molecules 2015, 19, 10103–10114.
- 23A. Scozzafava, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 1999, 14, 343–363.
- 24F. Özbey, P. Taslimi, I. Gulcin, A. Maras, S. Goksu, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31(S2), 79–85.
- 25K. Oktay, L. Polat Köse, K. Sendil, M. S. Gültekin, I. Gülçin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 939–945.
- 26T. Artunç, Y. Çetinkaya, H. Goçer, I. Gulçin, A. Menzek, E. Sahin, C. T. Supuran, Chem. Biol. Drug Des. 2016, 87, 594–607.
- 27I. Gülçin, S. Beydemir, M. E. Büyükokuroglu, Biol. Pharm. Bull. 2004, 27, 613–616.
- 28F. Z. Küçükbay, H. Küçükbay, M. Tanc, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1476–1483.
- 29A. Innocenti, S. B. Özturk Sarıkaya, I. Gülçin, C. T. Supuran, Bioorg. Med. Chem. 2010, 18, 2159–2164.
- 30P. Taslimi, I. Gülçin, N. Öztaşkın, Y. Çetinkaya, S. Göksu, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 603–607.
- 31A. Akıncıoğlu, H. Akıncıoğlu, I. Gülçin, S. Durdagi, C. T. Supuran, S. Goksu, Bioorg. Med. Chem. 2015, 23, 3592–3602.
- 32I. Gülçin, A. Scozzafava, C. T. Supuran, Z. Koksal, F. Turkan, S. Çetinkaya, Z. Bingöl, Z. Huyut, S. H. Alwasel, J. Enzyme Inhib. Med. Chem. 2016, 31, 1698–1702.
- 33C. Temperini, A. Scozzafava, D. Vullo, C. T. Supuran, Chemistry 2006; 12, 7057–7066.
- 34H. Göksu, M. Topal, A. Keskin, M. S. Gultekin, M. Çelik, I. Gulcin, M. Tanc, C. T. Supuran, Arch. Pharm. 2016, 349, 466–474.
- 35K. Aksu, M. Nar, M. Tanc, D. vullo, I. Gulcin, S. Goksu, F. Tümer, C. T. Supuran, Bioorg. Med. Chem. 2013, 21, 2925–2931.
- 36A. Yıldırım, U. Atmaca, A. Keskin, M. Topal, M. Çelik, I. Gülçin, C. T. Supuran, Bioorg. Med. Chem. 2015, 23, 2598–2605.
- 37H. I. Gül, M. Tugrak, H. Sakagami, P. Taslimi, I. Gülçin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1619–1624.
- 38A. Sujayev, E. Garibov, P. Taslimi, I. Gülçin, S. Gojayeva, V. Farzaliyev, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1531–1539.
- 39S. Göksu, A. Naderi, Y. Akbaba, P. Kalın, A. Akıncıoglu, I. Gulcin, S. Durdagi, R. E. Salmas, Bioorg. Chem. 2014, 56, 75–82.
- 40C. T. Supuran, Nat. Rev. Drug Discov. 2008, 7, 168–181.
- 41T. A. Coban, S. Beydemir, I. Gülçin, D. Ekinci, Biol. Pharm. Bull. 2007, 30, 2257–2261.
- 42M. Sentürk, I. Gülçin, S. Beydemir, Ö. I. Küfrevioglu, C. T. Supuran, Chem. Biol. Drugs Des. 2011, 77, 494–499.
- 43N. Oztaşkın, Y. Çetinkaya, P. Taslimi, S. Göksu, I. Gulçin, Bioorg. Chem. 2015, 60, 49–57.
- 44P. Taslimi, I. Gulcin, B. Ozgeris, S. Goksu, F. Tumer, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 152–157.
- 45B. Turan, K. Sendil, E. Sengul, M. S. Gultekin, P. Taslimi, I. Gulcin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31(S1), 79–88.
- 46K. Aksu, B. Ozgeriş, P. Taslimi, A. Naderi, I. Gulçin, S. Goksu, Arch. Pharm. 2016, 349, 944–954.
- 47H. I. Gül, A. Demirtas, G. Ucar, P. Taslimi, I. Gulcin, Let. Drug Des. Discov. 2017, 14, 573–580.
- 48P. Taslimi, A. Sujayev, S. Mamedova, P. Kalın, I. Gulcin, N. Sadeghian, S. Beydemir, O. F. Kufrevioglu, S. H. Alwasel, V. Farzaliyev, S. Mamedov, J. Enzyme Inhib. Med. Chem. 2017, 32, 137–145.
- 49P. Taslimi, A. Sujayev, E. Garibov, N. Nazarov, Z. Huyut, S. H. Alwasel, I. Gulcin, J. Biochem. Mol. Toxicol. 2017, https://doi.org/10.1002/jbt.21897.
- 50M. Nar, Y. Çetinkaya, I. Gülçin, A. Menzek, J. Enzyme Inhib. Med. Chem. 2013, 28, 402–406.
- 51O. Hisar, S. Beydemir, I. Gülçin, S. ArasHisar, T. Yanık, Ö. I. Küfrevioglu, Turk. J. Vet. Anim. Sci. 2005, 29, 841–845.
- 52A. Sujayev, L. Polat Kose, E. Garibov, I. Gulcin, V. Farzaliev, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med Chem. 2016, 31, 1192–1197.
- 53M. Topal, I. Gülçin, Turk. J. Chem. 2014, 38, 894–902.
- 54D. Ozmen Ozgun, C. Yamali, H. I. Gül, P. Taslimi, I. Gülçin, T. Yanik, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 1498–1501.
- 55H. I. Gül, K. Kucukoglu, C. Yamali, S. Bilginer, H. Yuca, I. Ozturk, P. Taslimi, I. Gülçin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31, 568–573.
- 56M. Küçük, I. Gulcin, Environ. Toxicol. Pharmacol. 2016, 44, 134–139.
- 57M. Güney, A. Coskun, F. Topal, A. Dastan, I. Gülçin, C. T. Supuran, Bioorg. Med. Chem. 2014, 22, 3537–3543.
- 58F. Topal, M. Topal, H. Gocer, P. Kalın, U. M. Koçyigit, I. Gülçin, S. H. Alwasel, J. Enzyme Inhib. Med. Chem. 2016, 31, 674–683.
- 59J. A. Verpoorte, S. Mehta, J. T. Edsall, J. Biol. Chem. 1967, 242, 4221–4229.
- 60U. M. Kocyigit, O. Nuri Aslan, I. Gulcin, Y. Temel, M. Ceylan, Arch. Pharm. 2016, 349, 955–963.
- 61A. Kamal, A. Basha Shaik, N. Reddy, G. Kumar, J. Joseph, B. Kumar, U. Purushotham, N. Sastry, Med. Chem. Res. 2014, 23, 2080–2092.
- 62H. I. Gül, E. Mete, P. Taslimi, I. Gulcin, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2017, 32, 189–192.
- 63H. Lineweaver, D. Burk, J. Am. Chem. Soc. 1934, 56, 658–666.
- 64G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherston, Biochem. Pharmacol. 1961, 7, 88–95.
- 65L. Polat Köse, I. Gulçin, A. C. Gören, J. Namiesnik, A. L. Martinez-Ayala, S. Gorinstein, Ind. Crops Prod. 2015, 74, 712–721.
- 66Y. Camadan, H. Özdemir, I. Gulcin, J. Enzyme Inhib. Med. Chem. 2016, 31, 1335–1341.
- 67H. Gocer, A. Akıncıoğlu, N. Öztaskın, S. Goksu, I. Gulcin, Arch. Pharm. 2013, 346, 783–792.
- 68K. Aksu, F. Topal, I. Gülçin, F. Tümer, S. Göksu, Arch. Pharm. 2015, 348, 446–455.
- 69A. Innocenti, I. Gülçin, A. Scozzafava, C. T. Supuran, Bioorg. Med. Chem. Lett. 2010, 20, 5050–5053.
- 70Y. Akbaba, E. Bastem, F. Topal, I. Gülçin, A. Maras, S. Göksu, Arch. Pharm. 2014, 347, 950–957.
- 71M. Ceylan, U. M. Kocyigit, N. C. Usta, B. Gürbüzlü, Y. Temel, S. H. Alwasel, İ. Gulcin. J. Biochem. Mol. Toxicol. https://doi.org/10.1002/jbt.21872.
- 72F. Topal, İ. Gulcin, A. Dastan, M. Guney, Int. J. Biol. Macromol. 2017, 94, 845–851.
- 73T. Gokcen, M. Al, M. Topal, I. Gulcin, T. Ozturk, A. C. Goren, Org. Commun. 2017, 10, 15–23.
- 74U. M. Kocyigit, Y. Budak, M. B. Gürdere, S. Tekin, T. K. Köprülü, F. Ertürk, K. Özcan, I. Gülçin, M. Ceylan, Bioorg. Chem. 2017, 70, 118–125.