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Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group

Yıl 2024, Cilt: 8 Sayı: 1, 19 - 26

Bedriye Seda Kurşun Aktar

https://doi.org/10.32571/ijct.1389889

Öz

A series of new chalcone derivatives (1-5) were synthesized as a result of the Claisen-Schmidt condensation of different substituted methyl aldehydes of 4′-Piperazinoacetophenone. Anticholinesterase (AChE and BChE) inhibitory activity and antidiabetic (α-glucosidase and α-amylase inhibitory) activities of the synthesized compounds were examined. While compound 1 is the most active molecule in AChE (IC50= 16.29±0.44 μM), BChE (IC50 = 10.19±0.04 μM) and α-amylase (IC50= 105.51±0.24 μM) inhibitor activities; Compound 5 was found to be the most active molecule in α-glucosidase inhibitor activity. In silico and molecular docking studies of compounds 1-5 were performed. According to molecular docking results, all molecules were found to be more active than the reference compounds.

Anahtar Kelimeler

Chalcone anticholinesterase inhibitory α-amylase inhibitory α-glycosidase inhibitory molecular docking

Kaynakça

  • 1.Ha, M.T.; Seong, S.H.; Nguyen, T.D.; Cho, W.K.; Ah, K.J.; Mae, J.Y.; Woo, M.H.; Choi, J.S.; Min, B.S. Phytochemistry. 2018, 155, 114–125.
  • 2. Aktar, B.S.K.; Sıcak, Y.; Tok, T.T.; Emre, O.E.E.; Yağlıoğlu, A.Ş.; Iyidoğan, A.K.; Demirtaş, I. J. Mol. Struct. 2020,1211, 128059.
  • 3. Chen, M.; Christensen, S.B.; Blom, J.; Lemmich, E.; Nadelmann, L.; Fich, K.; Kharazmi, A. Antimicrob. Agents Chemother. 1993, 37(12), 2550-2556.
  • 4. Birari, R.B.; Gupta, S.; Mohan, C.G.; Bhutani, K.K. Phytomedicine. 2011, 18(8-9), 795-801.
  • 5. Aktar, B.S.K.; Sıcak, Y.; Emre, O.E.E. Int. J. Chem. Technol. 2022, 6(1), 7-14.
  • 6. Tomar, V.; Bhattacharjee, G.; Rajakumar, S.; Srivastava, K.; Puri, S. K. Eur. J. Med. Chem. 2010, 45(2), 745-751.
  • 7. Sashidhara, K.V.; Palnati, G.R.; Sonkar, R.; Avula, S.R.; Awasthi, C.; Bhatia, G. Eur. J. Med. Chem. 2013, 64, 422-431.
  • 8. Wang, J.; Wang, N.; Yao, X.; Kitanaka, S.亚洲传统医药, 2007, 2(1), 23-29.
  • 9. Rizvi, S.U.F.; Siddiqui, H.L.; Johns, M.; Detorio, M.; Schinazi, R.F. 2012. Med. Chem. Res. 21, 3741-3749.
  • 10. Israf, D.A.; Khaizurin, T.A.; Syahida, A.; Lajis, N.H.; Khozirah, S. Mol. Immunol. 2007, 44(5), 673-679.
  • 11. Lee, Y.S.; Lim, S.S.; Shin, K.H.; Kim, Y.S.; Ohuchi, K.; Jung, S.H. Biol. Pharm. Bull. 2006, 29(5), 1028-1031.
  • 12. Kim, D.W.; Curtis-Long, M.J.; Yuk, H.J.; Wang, Y.; Song, Y.H.; Jeong, S.H.; Park, K.H. Food chemistry. 2014,153, 20-27. 13. Abdullah, M.I.; Mahmood, A.; Madni, M.; Masood, S.; Kashif, M. Bioorg. Chem. 2014, 54, 31-37.
  • 14. Mahapatra, D.K.; Asati, V.; Bharti, S.K. 2015, Eur. J. Med. Chem. 92, 839-865.
  • 15. Cho, S.; Kim, S.; Jin, Z.; Yang, H.; Han, D.; Baek, N.I.; Jin, Y.H. Biochemical and Biochem. Biophys. Res. Commun. 2011, 413(4), 637-642.
  • 16. Alsayed, S.S.; Beh, C.C.; Foster, N.R.; Payne, A.D.; Yu, Y.; Gunosewoyo, H. Current Mol. Pharmacol. 2019, 12(1), 27-49.
  • 17. Jamal, H.; Ansari, W.H.; Rizvi, S.J. Fund. Clin. Pharmacol. 2008, 22(6), 673-681.
  • 18. Kursun Aktar, B.S.; Oruç-Emre, E.E.; Demirtas¸ I., Sahin Yaglioglu, A.; Guler, C.; Adem, S.; Karaküçük Iyidogan, A. J. Mol. Struct. 2017, 1149, 632-639.
  • 19. Ranjit, P.M.; Rahaman, S.A.; Kumar, K.P.; Prasad, Y.R.; Santhipriya, T.; Manikanta, G.C. V.S.; Sudeepthi, N.R.L. Int. J. PharmTech Res, 2013,5(1), 284-293.
  • 20. Ellman, G.L.; Courtney, K.D.; Andres, V.; Featherston, R.M. Biochem. Pharmacol. 1961, 7, 88-95.
  • 21. Quan, N.; Xuan, T.; Tran, H.D.; Thuy, N.; Trang, L.; Huong, C.; Tuyen, P. Molecules. 2019, 24(3), 605.
  • 22. Kim, J.S.; Kwon, C.S.; Son, K.H. Biosci. Biotechnol. Biochem. 2000, 64(11), 2458-2461.
  • 23. Adme Daina, A.; Michielin, O.; Zoete, V. Sci. Rep. 2017, 7(1), 42717.
  • 24. Mol Molsoft molecules in silico. http://molsoft.com/ mprop (Accessed September 9, 2023)
  • 25. Organic Chemistry Portal. https://www.organic-chemistry.org/ (Accessed on 20 May 2023).
  • 26. Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belw, R.K.; Goodsell, D.S.; Olson, A.J. J. Comput. Chem. 2009, 30(16), 2785-2791.
  • 27. Sıcak, Y.; Kekeçmuhammed, H.; Karaküçük‐İyidoğan, A.; Taşkın‐Tok, T.; Oruç‐Emre, E. E.; Öztürk, M. J. Mol. Recognit. 2023, e3020.
  • 28. Aktar, B. S. K. Russ. J. Bioorg. Chem. 2023, 49(5), 1023-1033.
  • 29. Kurşun‐Aktar, B.S.; Adem, Ş.; Tatar‐Yilmaz, G.; Hameed, Z.A.H.; Oruç‐Emre, E.E. J. Mol. Recognit, 2023, e3061.
  • 30. Sıcak, Y. Med. Chem. Res. 2021, 30(8), 1557-1568.
  • 31. Sıcak, Y. Turk J Chem. 2021, DOI: 10.3906/kim-2107-27.
  • 32. Barak, D.; Kronman, C.; Ordentlich, A.; Ariel, N.; Bromberg, A.; Marcus, D; Shafferman, A. J. Biol. Chem. 1994, 269(9), 6296-6305.
  • 33. Quinn, D.M. Chemical reviews. 1987,87(5), 955-979.
  • 34. Masson, P.; Legrand, P.; Bartels, C.F.; Froment, M.T.; Schopfer, L.M.; Lockridge, O. Biochemistry. 1997,36(8), 2266-2277.
  • 35. Nachon, F.; Ehret-Sabatier, L.; Loew, D.; Colas, C.; van Dorsselaer, A.; Goeldner, M. Biochemistry. 1998, 37(29), 10507-10513.
  • 36. Williams, L.K.; Zhang, X.; Caner, S.; Tysoe, C.; Nguyen, N.T.; Wicki, J.; Brayer, G.D. The amylase inhibitor montbretin A reveals a new glycosidase inhibition motif. Nat. Chem. Biol. 2015, 11(9), 691-696.
  • 37. Roig-Zamboni, V.; Cobucci-Ponzano, B.; Iacono, R.; Ferrara, M. C.; Germany, S.; Bourne, Y.; Sulzenbacher, G. Nat. Commun, 2017, 8(1), 1111.
  • 38. Williams, L.K.; Zhang, X.; Caner, S.; Tysoe, C.; Nguyen, N.T.; Wicki, J.; Brayer, G.D. 2015. Nat. Chem. Biol. 11(9), 691-696

Yıl 2024, Cilt: 8 Sayı: 1, 19 - 26

Bedriye Seda Kurşun Aktar

https://doi.org/10.32571/ijct.1389889

Öz

Kaynakça

  • 1.Ha, M.T.; Seong, S.H.; Nguyen, T.D.; Cho, W.K.; Ah, K.J.; Mae, J.Y.; Woo, M.H.; Choi, J.S.; Min, B.S. Phytochemistry. 2018, 155, 114–125.
  • 2. Aktar, B.S.K.; Sıcak, Y.; Tok, T.T.; Emre, O.E.E.; Yağlıoğlu, A.Ş.; Iyidoğan, A.K.; Demirtaş, I. J. Mol. Struct. 2020,1211, 128059.
  • 3. Chen, M.; Christensen, S.B.; Blom, J.; Lemmich, E.; Nadelmann, L.; Fich, K.; Kharazmi, A. Antimicrob. Agents Chemother. 1993, 37(12), 2550-2556.
  • 4. Birari, R.B.; Gupta, S.; Mohan, C.G.; Bhutani, K.K. Phytomedicine. 2011, 18(8-9), 795-801.
  • 5. Aktar, B.S.K.; Sıcak, Y.; Emre, O.E.E. Int. J. Chem. Technol. 2022, 6(1), 7-14.
  • 6. Tomar, V.; Bhattacharjee, G.; Rajakumar, S.; Srivastava, K.; Puri, S. K. Eur. J. Med. Chem. 2010, 45(2), 745-751.
  • 7. Sashidhara, K.V.; Palnati, G.R.; Sonkar, R.; Avula, S.R.; Awasthi, C.; Bhatia, G. Eur. J. Med. Chem. 2013, 64, 422-431.
  • 8. Wang, J.; Wang, N.; Yao, X.; Kitanaka, S.亚洲传统医药, 2007, 2(1), 23-29.
  • 9. Rizvi, S.U.F.; Siddiqui, H.L.; Johns, M.; Detorio, M.; Schinazi, R.F. 2012. Med. Chem. Res. 21, 3741-3749.
  • 10. Israf, D.A.; Khaizurin, T.A.; Syahida, A.; Lajis, N.H.; Khozirah, S. Mol. Immunol. 2007, 44(5), 673-679.
  • 11. Lee, Y.S.; Lim, S.S.; Shin, K.H.; Kim, Y.S.; Ohuchi, K.; Jung, S.H. Biol. Pharm. Bull. 2006, 29(5), 1028-1031.
  • 12. Kim, D.W.; Curtis-Long, M.J.; Yuk, H.J.; Wang, Y.; Song, Y.H.; Jeong, S.H.; Park, K.H. Food chemistry. 2014,153, 20-27. 13. Abdullah, M.I.; Mahmood, A.; Madni, M.; Masood, S.; Kashif, M. Bioorg. Chem. 2014, 54, 31-37.
  • 14. Mahapatra, D.K.; Asati, V.; Bharti, S.K. 2015, Eur. J. Med. Chem. 92, 839-865.
  • 15. Cho, S.; Kim, S.; Jin, Z.; Yang, H.; Han, D.; Baek, N.I.; Jin, Y.H. Biochemical and Biochem. Biophys. Res. Commun. 2011, 413(4), 637-642.
  • 16. Alsayed, S.S.; Beh, C.C.; Foster, N.R.; Payne, A.D.; Yu, Y.; Gunosewoyo, H. Current Mol. Pharmacol. 2019, 12(1), 27-49.
  • 17. Jamal, H.; Ansari, W.H.; Rizvi, S.J. Fund. Clin. Pharmacol. 2008, 22(6), 673-681.
  • 18. Kursun Aktar, B.S.; Oruç-Emre, E.E.; Demirtas¸ I., Sahin Yaglioglu, A.; Guler, C.; Adem, S.; Karaküçük Iyidogan, A. J. Mol. Struct. 2017, 1149, 632-639.
  • 19. Ranjit, P.M.; Rahaman, S.A.; Kumar, K.P.; Prasad, Y.R.; Santhipriya, T.; Manikanta, G.C. V.S.; Sudeepthi, N.R.L. Int. J. PharmTech Res, 2013,5(1), 284-293.
  • 20. Ellman, G.L.; Courtney, K.D.; Andres, V.; Featherston, R.M. Biochem. Pharmacol. 1961, 7, 88-95.
  • 21. Quan, N.; Xuan, T.; Tran, H.D.; Thuy, N.; Trang, L.; Huong, C.; Tuyen, P. Molecules. 2019, 24(3), 605.
  • 22. Kim, J.S.; Kwon, C.S.; Son, K.H. Biosci. Biotechnol. Biochem. 2000, 64(11), 2458-2461.
  • 23. Adme Daina, A.; Michielin, O.; Zoete, V. Sci. Rep. 2017, 7(1), 42717.
  • 24. Mol Molsoft molecules in silico. http://molsoft.com/ mprop (Accessed September 9, 2023)
  • 25. Organic Chemistry Portal. https://www.organic-chemistry.org/ (Accessed on 20 May 2023).
  • 26. Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belw, R.K.; Goodsell, D.S.; Olson, A.J. J. Comput. Chem. 2009, 30(16), 2785-2791.
  • 27. Sıcak, Y.; Kekeçmuhammed, H.; Karaküçük‐İyidoğan, A.; Taşkın‐Tok, T.; Oruç‐Emre, E. E.; Öztürk, M. J. Mol. Recognit. 2023, e3020.
  • 28. Aktar, B. S. K. Russ. J. Bioorg. Chem. 2023, 49(5), 1023-1033.
  • 29. Kurşun‐Aktar, B.S.; Adem, Ş.; Tatar‐Yilmaz, G.; Hameed, Z.A.H.; Oruç‐Emre, E.E. J. Mol. Recognit, 2023, e3061.
  • 30. Sıcak, Y. Med. Chem. Res. 2021, 30(8), 1557-1568.
  • 31. Sıcak, Y. Turk J Chem. 2021, DOI: 10.3906/kim-2107-27.
  • 32. Barak, D.; Kronman, C.; Ordentlich, A.; Ariel, N.; Bromberg, A.; Marcus, D; Shafferman, A. J. Biol. Chem. 1994, 269(9), 6296-6305.
  • 33. Quinn, D.M. Chemical reviews. 1987,87(5), 955-979.
  • 34. Masson, P.; Legrand, P.; Bartels, C.F.; Froment, M.T.; Schopfer, L.M.; Lockridge, O. Biochemistry. 1997,36(8), 2266-2277.
  • 35. Nachon, F.; Ehret-Sabatier, L.; Loew, D.; Colas, C.; van Dorsselaer, A.; Goeldner, M. Biochemistry. 1998, 37(29), 10507-10513.
  • 36. Williams, L.K.; Zhang, X.; Caner, S.; Tysoe, C.; Nguyen, N.T.; Wicki, J.; Brayer, G.D. The amylase inhibitor montbretin A reveals a new glycosidase inhibition motif. Nat. Chem. Biol. 2015, 11(9), 691-696.
  • 37. Roig-Zamboni, V.; Cobucci-Ponzano, B.; Iacono, R.; Ferrara, M. C.; Germany, S.; Bourne, Y.; Sulzenbacher, G. Nat. Commun, 2017, 8(1), 1111.
  • 38. Williams, L.K.; Zhang, X.; Caner, S.; Tysoe, C.; Nguyen, N.T.; Wicki, J.; Brayer, G.D. 2015. Nat. Chem. Biol. 11(9), 691-696
Toplam 37 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Yapısal Biyoloji
Bölüm Makale
Yazarlar

Bedriye Seda Kurşun Aktar 0000-0002-1492-3266

Erken Görünüm Tarihi 27 Mart 2024
Yayımlanma Tarihi
Gönderilme Tarihi 13 Kasım 2023
Kabul Tarihi 29 Aralık 2023
Yayımlandığı Sayı Yıl 2024 Cilt: 8 Sayı: 1

Kaynak Göster

APA Kurşun Aktar, B. S. (2024). Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group. International Journal of Chemistry and Technology, 8(1), 19-26. https://doi.org/10.32571/ijct.1389889
AMA Kurşun Aktar BS. Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group. Int. J. Chem. Technol. Mart 2024;8(1):19-26. doi:10.32571/ijct.1389889
Chicago Kurşun Aktar, Bedriye Seda. “Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds With Methyl Group”. International Journal of Chemistry and Technology 8, sy. 1 (Mart 2024): 19-26. https://doi.org/10.32571/ijct.1389889.
EndNote Kurşun Aktar BS (01 Mart 2024) Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group. International Journal of Chemistry and Technology 8 1 19–26.
IEEE B. S. Kurşun Aktar, “Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group”, Int. J. Chem. Technol., c. 8, sy. 1, ss. 19–26, 2024, doi: 10.32571/ijct.1389889.
ISNAD Kurşun Aktar, Bedriye Seda. “Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds With Methyl Group”. International Journal of Chemistry and Technology 8/1 (Mart 2024), 19-26. https://doi.org/10.32571/ijct.1389889.
JAMA Kurşun Aktar BS. Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group. Int. J. Chem. Technol. 2024;8:19–26.
MLA Kurşun Aktar, Bedriye Seda. “Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds With Methyl Group”. International Journal of Chemistry and Technology, c. 8, sy. 1, 2024, ss. 19-26, doi:10.32571/ijct.1389889.
Vancouver Kurşun Aktar BS. Synthesis, Biological Activity Studies and Molecular Modeling Studies of Chalcone Compounds with Methyl Group. Int. J. Chem. Technol. 2024;8(1):19-26.

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