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

Bedriye Seda Kurşun Aktar

doi:10.32571/ijct.1389889

Research Article

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

Year 2024, Volume: 8 Issue: 1, 19 - 26

Bedriye Seda Kurşun Aktar

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.

Keywords

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

References

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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

Year 2024, Volume: 8 Issue: 1, 19 - 26

Bedriye Seda Kurşun Aktar

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

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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
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. March 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 (March 2024): 19-26. https://doi.org/10.32571/ijct.1389889.
EndNote	Kurşun Aktar BS (March 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 (March 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.

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