Abstract
A convenient and efficient reaction for the synthesis of several new bis-hydroxy derivatives of chalcones 4a–h was accomplished via the two-directional Claisen–Schmidt condensation of different ketones 3a–e with premade benzaldehyde 2 under alkaline conditions. Products were obtained with reasonable yields and with excellent purity. The in vitro antioxidant activity of bis-hydroxychalcones was assessed by DPPH radical scavenging activity in comparison with ascorbic acid, and products showed good antioxidant activity. To determine the possible binding mechanisms with the active site of tubulin and bovine xanthine oxidase (BXO), docking analyses were performed. According to the docking results, compounds 4b and 4a showed the best binding affinity of − 9.13 and − 9.11 kcal/mol for tubulin, respectively. Furthermore, as before, the greatest scores for the case of BXO belong to 4b and 4a with the scores of the values − 10.32 and − 9.81 kcal/mol.
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References
H. Venkatachalam, N. Yogendra, B.S. Jayashree, Int. J. Chem. 3, 216 (2012)
N.O. Mahmoodi, M.M. Zeydi, M. Mamaghani, N. Montazeri, Res. Chem. Intermed. 43, 2641 (2017)
N.O. Mahmoodi, B. Sharifzadeh, M. Mamaghani, K. Tabatabaeian, J. Heterocycl. Chem. 51, 336 (2014)
M.S. Yoo, D.G. Kim, M.W. Ha, S.S. Jew, H.G. Park, B.S. Jeong, Tetrahedron Lett. 51, 5601 (2010)
A. Tafi, R. Costi, M. Botta, R. Di Santo, F. Corelli, S. Massa, M. Artico, J. Med. Chem. 45, 2720 (2002)
G. Di Carlo, N. Mascolo, A.A. Izzo, F. Capasso, Flavonoids. Life Sci. 65, 337 (1999)
N.K. Sahu, S.S. Balbhadra, J. Choudhary, D.V. Kohli, Curr. Med. Chem. 19, 209 (2012)
A. Rammohan, J.S. Reddy, G. Sravya, C.N. Rao, G.V. Zyryanov, Environ. Chem. Lett. 18, 433 (2020)
A. Hameed, S. Masood, A. Hameed, E. Ahmed, A. Sharif, M.I. Abdullah, J. Comput. Aided Mol. Des. 33, 677 (2019)
X. Gan, Y. Wang, D. Hu, B. Song, Chin. J. Chem. 35, 665 (2017)
S. Khanapure, M. Jagadale, P. Bansode, P. Choudhari, G. Rashinkar, J. Mol. Struct. 1173, 142 (2018)
M. Bazzaro, R.K. Anchoori, M.K.R. Mudiam, O. Issaenko, S. Kumar, B. Karanam, S.R. Khan, J. Med. Chem. 54, 449 (2011)
J. Wu, J. Li, Y. Cai, Y. Pan, F. Ye, Y. Zhang, G. Liang, J. Med. Chem. 54, 8110 (2011)
X. Fang, B. Yang, Z. Cheng, P. Zhang, M. Yang, Res. Chem. Intermed. 40, 1715 (2014)
L.M. Zhao, H.S. Jin, L.P. Sun, H.R. Piao, Z.S. Quan, Bioorganic Med Chem. Lett. 15, 5027 (2005)
A.E. Maatougui, M. Yáñez, A. Crespo, N. Fraiz, A. Coelho, E. Ravina, E. Sotelo, ChemistrySelect 2, 4920 (2017)
M.M. Kabanda, S. Gbashi, N.E. Madala, Free Radic. Res. 5, 53 (2021)
S. Ducki, Anticancer Agents Med Chem. 9, 336 (2009)
M.A. Jordan, L. Wilson, Nat. Rev. Cancer. 4, 253 (2004)
C. Dumontet, M.A. Jordan, Nat. Rev. Drug Discov. 9, 790 (2010)
S. Sengupta, S.A. Thomas, Expert Rev. Anticancer Ther. 6, 1433 (2006)
R.O. Carlson, Expert Opin. Investig. Drugs 17, 707 (2008)
G. Wang, Z. Peng, J. Zhang, J. Qiu, Z. Xie, Z. Gong, Bioorg. Chem. 78, 332 (2018)
S. Mirzaei, F. Hadizadeh, F. Eisvand, F. Mosaffa, R. Ghodsi, J. Mol. Struct. 1202, 127310 (2020)
G. Wang, W. Liu, Z. Gong, Y. Huang, Y. Li, Z. Peng, Bioorg. Chem. 95, 103565 (2020)
A. Hammuda, S. Rovida, D.E. Edmondson, C. Binda, A. Khalil, Eur. J. Med. Chem. 114, 162 (2016)
J. Li, N. Zhou, K. Luo, W. Zhang, X. Li, C. Wu, Int. J. Mol. Sci. 15, 15994 (2014)
N.O. Mahmoodi, Z. Khazaei, J. Iran. Chem. Soc. 14, 1889 (2017)
S. Shoja, N.O. Mahmoodi, H. Ghafoori, M. Rassa, A. Sharafshah, E. Panahi Kokhdan, Res. Chem. Intermed. 46, 3327 (2020)
Schrödinger Release 2018–1: maestro; Schrödinger, LLC: New York, NY, USA, 2018.
R.B. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, M. Knossow, M. Nature 428 198 (2004).
J.C. Shelley, A. Cholleti, L.L. Frye, J.R. Greenwood, M.R. Timlin, M. Uchimaya, J. Comput. Aided Mol. Des. 21, 681 (2007)
G.M. Sastry, M. Adzhigirey, T. Day, R. Annabhimoju, W. Sherman, J. Comput. Aided Mol. Des. 27, 221 (2013)
D. Shivakumar, J. Williams, Y. Wu, W. Damm, J. Shelley, W. Sherman, J. Chem. Theory Comput. 6, 1509 (2010)
R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, D.T. Mainz, J. Med. Chem. 49, 6177 (2006)
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The authors are grateful to the Research Council of the University of Guilan for financial support of this research work.
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Miss ZK-P zahrakhazaei69@gmail.com. Wrote the main manuscript text, prepared all figures, designed and directed the project, performed the synthesis, biological evaluation, analyzed spectra, and made the simulations; Dr. HTN H_taherpour@pnu.ac.ir. Developed the theoretical framework and molecular docking studies; Dr. NOM supervised and reviewed the manuscript, mahmoodi@guilan.ac.ir and nosmahmoodi@gmail.com.
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Khazaei-Poul, Z., Mahmoodi, N.O. & Taherpour Nahzomi, H. Synthesis, biological evaluation and molecular docking studies of a new series of bis-chalcones. Res Chem Intermed 49, 273–287 (2023). https://doi.org/10.1007/s11164-022-04872-w
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DOI: https://doi.org/10.1007/s11164-022-04872-w