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

Year 2024, Volume: 8 Issue: 1, 19 - 26, 05.06.2024
https://doi.org/10.32571/ijct.1389889

Abstract

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.

References

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Year 2024, Volume: 8 Issue: 1, 19 - 26, 05.06.2024
https://doi.org/10.32571/ijct.1389889

Abstract

References

  • 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
There are 37 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Research Articles
Authors

Bedriye Seda Kurşun Aktar 0000-0002-1492-3266

Early Pub Date March 27, 2024
Publication Date June 5, 2024
Submission Date November 13, 2023
Acceptance Date December 29, 2023
Published in Issue Year 2024 Volume: 8 Issue: 1

Cite

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. June 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, no. 1 (June 2024): 19-26. https://doi.org/10.32571/ijct.1389889.
EndNote Kurşun Aktar BS (June 1, 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., vol. 8, no. 1, pp. 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 (June 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, vol. 8, no. 1, 2024, pp. 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.