Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Docking, Synthesis and Anticancer Activity of 4-(4-(3-(4-Chloro-3-(trifluoromethyl)- phenyl)ureido)phenoxy)-N-(2-morpholinoethyl)picolinamide Derivatives
Corresponding Author(s) : Vanita Marvaniya
Asian Journal of Chemistry,
Vol. 34 No. 6 (2022): Vol 34 Issue 6
Abstract
A new series of diaryl urea derivatives bearing pyridine moiety were designed, synthesized and evaluated for their biological activity. In this study, we applied the structure-based virtual screening (SBVS) on the high similar sorafenib approved drug, selected from the DrugBank database as well as on a series of derivatives, selected from the literature. Aim was to provide new potent anticancer agents. Analysis was performed using AutoDock VINA tools. Based on the ligand binding energy. Compounds will be synthesized by chlorination of pyridine acid derivative which further coupled with amine and form amide, amide further reaction with aminophenolic moiety and form ether which is react with other aromatic amine using CDI to produce final compound and these compounds characterized by IR, NMR and mass spectroscopic techniques. The synthesized derivatives have been evaluated to their anticancer activity in vitro by MTT assay using MCF-7 cell line. The anticancer activity indicates that compounds C1, C3, C6 and C9 have better anticancer activity.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- Z. Momenimovahed and H. Salehiniya, Breast Canc. Targ. Therap., 11, 151 (2019); https://doi.org/10.2147/BCTT.S176070
- R. Siegel, D. Naishadham and A. Jemal, CA Cancer J. Clin., 63, 11 (2013); https://doi.org/10.3322/caac.21166
- D.M. Keefe and E.H. Bateman, Nat. Rev. Clin. Oncol., 9, 98 (2012); https://doi.org/10.1038/nrclinonc.2011.192
- M. Ghorab, M. Alsaid, A.M. Soliman and A.A. Al-Mishari, J. Enzyme Inhib. Med. Chem., 33, 67 (2018); https://doi.org/10.1080/14756366.2017.1389922
- X. Tao, Y. Duan, L.-W. Chen, D.-J. Tang, M.-R. Yang, P.-F. Wang, C. Xu and H.-L. Zhu, Bioorg. Med. Chem. Lett., 26, 677 (2016); https://doi.org/10.1016/j.bmcl.2015.11.040
- R.A. Soo, S.M. Lim, N.L. Syn, R. Teng, R. Soong, T.S.K. Mok and B.C. Cho, Lung Cancer, 115, 12 (2018); https://doi.org/10.1016/j.lungcan.2017.11.009
- M. Pessoa, S. Alves, A.G. Taranto, J.A.F.P. Villar, G. Blanco and L.A. Barbosa, J. Enzyme Inhib. Med. Chem., 33, 85 (2018); https://doi.org/10.1080/14756366.2017.1380637
- T. Regad, Cancers, 7, 1758 (2015); https://doi.org/10.3390/cancers7030860
- M.G. Thabit, K.B. Selim, M.A.A. Elsayed and M.N.A. Nasr, Bioorg. Chem., 103, 104148 (2020); https://doi.org/10.1016/j.bioorg.2020.104148
- J.W. Anderson, D. Sarantakis, J. Terpinski, T.R. Santha Kumar, H.-C. Tsai, M. Kuo, A.L. Ager, W.R. Jacobs Jr., G.A. Schiehser, S. Ekins, J.C. Sacchettini, D.P. Jacobus, D.A. Fidock and J.S. Freundlich, Bioorg. Med. Chem. Lett., 23, 1022 (2015); https://doi.org/10.1016/j.bmcl.2012.12.022
- J.X. Qiao, T.C. Wang, R. Ruel, C. Thibeault, A. L’Heureux, W.A. Schumacher, S.A. Spronk, S. Hiebert, G. Bouthillier, J. Lloyd, Z. Pi, D.M. Schnur, L.M. Abell, J. Hua, L.A. Price, E. Liu, Q. Wu, T.E. Steinbacher, J.S. Bostwick, M. Chang, J. Zheng, Q. Gao, B. Ma, P.A. McDonnell, C.S. Huang, R. Rehfuss, R.R. Wexler and P.Y.S. Lam, J. Med. Chem., 56, 9275 (2013); https://doi.org/10.1021/jm4013906
- R.G. Kulkarni, S. Laufer, C. Mangannavar and A. Garlapati, Med. Chem., 9, 213 (2013); https://doi.org/10.2174/1573406411309020006
- A.P. Keche, G.D. Hatnapure, R.H. Tale, A.H. Rodge, S.S. Birajdar and V.M. Kamble, Bioorg. Med. Chem. Lett., 22, 3445 (2012); https://doi.org/10.1016/j.bmcl.2012.03.092
- H.J. Kim, H.J. Cho, H. Kim, M.I. El-Gamal, C.-H. Oh, S.H. Lee, T. Sim, J.-M. Hah and K.H. Yoo, Bioorg. Med. Chem. Lett., 22, 3269 (2012); https://doi.org/10.1016/j.bmcl.2012.03.020
- J. Feng, T. Li, S. Liang, C. Zhang, X. Tan, N. Ding, X. Wang, X. Liu and C. Hu, Med. Chem. Res., 29, 1413 (2020); https://doi.org/10.1007/s00044-020-02554-z
- A. Catalano, D. Iacopetta, M.S. Sinicropi and C. Franchini, Appl. Sci., 11, 374 (2021); https://doi.org/10.3390/app11010374
- A.D. Jagtap, N.B. Kondekar, A. Sadani and J.-W. Chern, Curr. Med. Chem., 24, 622 (2017); https://doi.org/10.2174/0929867323666161129124915
- P. Sikka, J.K. Sahu, A.K. Mishra and S.R. Hashim, Med. Chem., 5, 479 (2015); https://doi.org/10.4172/2161-0444.1000305
- A.K. Ghosh and M. Brindisi, J. Med. Chem., 63, 2751 (2020); https://doi.org/10.1021/acs.jmedchem.9b01541
- J.N. Chen and D.W. Wu, T. Li, K.-J. Yang, L. Cheng, Z.-P. Zhou, S.-M. Pu and W.-H. Lin, Curr. Top. Med. Chem., 17, 3099 (2017); https://doi.org/10.2174/1568026617666170707123553
- A. Elkamhawy and A.K. Farag, A.N.I. Viswanath, T.M. Bedair, D.G. Leem, K.-T. Lee, A.N. Pae and E.J. Roh, Bioorg. Med. Chem. Lett., 25, 5147 (2015); https://doi.org/10.1016/j.bmcl.2015.10.003
- L. Garuti, M. Roberti, G. Bottegoni and M. Ferraro, Curr. Med. Chem., 23, 1528 (2016); https://doi.org/10.2174/0929867323666160411142532
- M. El-Gamal and C.-H. Oh, Bull. Korean Chem. Soc., 33, 1571 (2012); https://doi.org/10.5012/bkcs.2012.33.5.1571
- P. Wu, T.E. Nielsen and M.H. Clausen, Trends Pharmacol. Sci., 36, 422 (2015); https://doi.org/10.1016/j.tips.2015.04.005
- Y. Aoki and Y. Matsubara, Int. J. Hematol., 97, 30 (2013); https://doi.org/10.1007/s12185-012-1239-y
- J. Dietrich, V. Gokhale, X. Wang, L.H. Hurley and G.A. Flynn, Bioorg. Med. Chem., 18, 292 (2010); https://doi.org/10.1016/j.bmc.2009.10.055
- M. Hussain, M. Baig, H.S.A. Mohamoud, Z. Ulhaq, D.C. Hoessli, G.S. Khogeer, R.R. Al-Sayed and J.Y. Al-Aama, Saudi J. Biol. Sci., 22, 359 (2015); https://doi.org/10.1016/j.sjbs.2014.10.002
- U. Ammar, M. Abdel-Maksoud and C.-H. Oh, Eur. J. Med. Chem., 158, 144 (2018); https://doi.org/10.1016/j.ejmech.2018.09.005
- Y. Wang, H. Nie, X. Zhao, Y. Qin and X. Gong, BMC Cancer, 16, 742 (2016); https://doi.org/10.1186/s12885-016-2767-2
- M. Kohler, S. Ehrenfeld, S. Halbach, M. Lauinger, U. Burk, N. Reischmann, S. Cheng, C. Spohr, F.M. Uhl, N. Köhler, K. Ringwald, S. Braun, C. Peters, R. Zeiser, T. Reinheckel and T. Brummer, Oncogene, 38, 1324 (2019); https://doi.org/10.1038/s41388-018-0663-8
- M. Abdel-Maksoud, M. El-Gamal, M.M. Gamal El-Din and C.H. Oh, J. Enzyme Inhib. Med. Chem., 34, 97 (2019); https://doi.org/10.1080/14756366.2018.1530225
- Kaur, P. Kaur, A. Mittal, S.K. Nayak and G.L. Khatik, Asian J. Pharm. Clin. Res., 10, 28 (2017); https://doi.org/10.22159/ajpcr.2017.v10s4.21332
- A. El Aissouq, O. Chedadi, M. Bouachrine and A. Ouammou, J. Chem., 2021, 1 (2021); https://doi.org/10.1155/2021/1901484
- R. Herowati and G.P. Widodo, Procedia Chem., 13, 63 (2014); https://doi.org/10.1016/j.proche.2014.12.007
- S.S. Qawoogha and A. Shahiwala, J. Recept. Signal Transduct. Res., 40, 67 (2020); https://doi.org/10.1080/10799893.2020.1715431
- W. Li, X. Zhai, Z. Zhong, G. Li, Y. Pu and P. Gong, Arch. Pharm. Chem. Life Sci., 11, 349 (2011); https://doi.org/10.1002/ardp.201000326
- C.S. Lu, K. Tang, Y. Li, B. Jin, D.L. Yin, C. Ma, X.G. Chen and H.H. Huang, Yao Xue Xue Bao, 48, 709 (2013)
- X. Kong, Z. Yao, Z. He, W. Xu and J. Yao, MedChemComm, 6, 867 (2015); https://doi.org/10.1039/C4MD00536H
- C. Wu, S. Xu, Y. Guo, J. Wu, R. Luo, W. Wang, Y. Tu, Le Chen, W. Zhu and P. Zheng, Med. Chem. Res., 27, 374 (2017); https://doi.org/10.1007/s00044-017-2045-0
- B. Moku, L. Ravindar, K.P. Rakesh and H.-L. Qin, Bioorg. Chem., 86, 513 (2019); https://doi.org/10.1016/j.bioorg.2019.02.030
References
Z. Momenimovahed and H. Salehiniya, Breast Canc. Targ. Therap., 11, 151 (2019); https://doi.org/10.2147/BCTT.S176070
R. Siegel, D. Naishadham and A. Jemal, CA Cancer J. Clin., 63, 11 (2013); https://doi.org/10.3322/caac.21166
D.M. Keefe and E.H. Bateman, Nat. Rev. Clin. Oncol., 9, 98 (2012); https://doi.org/10.1038/nrclinonc.2011.192
M. Ghorab, M. Alsaid, A.M. Soliman and A.A. Al-Mishari, J. Enzyme Inhib. Med. Chem., 33, 67 (2018); https://doi.org/10.1080/14756366.2017.1389922
X. Tao, Y. Duan, L.-W. Chen, D.-J. Tang, M.-R. Yang, P.-F. Wang, C. Xu and H.-L. Zhu, Bioorg. Med. Chem. Lett., 26, 677 (2016); https://doi.org/10.1016/j.bmcl.2015.11.040
R.A. Soo, S.M. Lim, N.L. Syn, R. Teng, R. Soong, T.S.K. Mok and B.C. Cho, Lung Cancer, 115, 12 (2018); https://doi.org/10.1016/j.lungcan.2017.11.009
M. Pessoa, S. Alves, A.G. Taranto, J.A.F.P. Villar, G. Blanco and L.A. Barbosa, J. Enzyme Inhib. Med. Chem., 33, 85 (2018); https://doi.org/10.1080/14756366.2017.1380637
T. Regad, Cancers, 7, 1758 (2015); https://doi.org/10.3390/cancers7030860
M.G. Thabit, K.B. Selim, M.A.A. Elsayed and M.N.A. Nasr, Bioorg. Chem., 103, 104148 (2020); https://doi.org/10.1016/j.bioorg.2020.104148
J.W. Anderson, D. Sarantakis, J. Terpinski, T.R. Santha Kumar, H.-C. Tsai, M. Kuo, A.L. Ager, W.R. Jacobs Jr., G.A. Schiehser, S. Ekins, J.C. Sacchettini, D.P. Jacobus, D.A. Fidock and J.S. Freundlich, Bioorg. Med. Chem. Lett., 23, 1022 (2015); https://doi.org/10.1016/j.bmcl.2012.12.022
J.X. Qiao, T.C. Wang, R. Ruel, C. Thibeault, A. L’Heureux, W.A. Schumacher, S.A. Spronk, S. Hiebert, G. Bouthillier, J. Lloyd, Z. Pi, D.M. Schnur, L.M. Abell, J. Hua, L.A. Price, E. Liu, Q. Wu, T.E. Steinbacher, J.S. Bostwick, M. Chang, J. Zheng, Q. Gao, B. Ma, P.A. McDonnell, C.S. Huang, R. Rehfuss, R.R. Wexler and P.Y.S. Lam, J. Med. Chem., 56, 9275 (2013); https://doi.org/10.1021/jm4013906
R.G. Kulkarni, S. Laufer, C. Mangannavar and A. Garlapati, Med. Chem., 9, 213 (2013); https://doi.org/10.2174/1573406411309020006
A.P. Keche, G.D. Hatnapure, R.H. Tale, A.H. Rodge, S.S. Birajdar and V.M. Kamble, Bioorg. Med. Chem. Lett., 22, 3445 (2012); https://doi.org/10.1016/j.bmcl.2012.03.092
H.J. Kim, H.J. Cho, H. Kim, M.I. El-Gamal, C.-H. Oh, S.H. Lee, T. Sim, J.-M. Hah and K.H. Yoo, Bioorg. Med. Chem. Lett., 22, 3269 (2012); https://doi.org/10.1016/j.bmcl.2012.03.020
J. Feng, T. Li, S. Liang, C. Zhang, X. Tan, N. Ding, X. Wang, X. Liu and C. Hu, Med. Chem. Res., 29, 1413 (2020); https://doi.org/10.1007/s00044-020-02554-z
A. Catalano, D. Iacopetta, M.S. Sinicropi and C. Franchini, Appl. Sci., 11, 374 (2021); https://doi.org/10.3390/app11010374
A.D. Jagtap, N.B. Kondekar, A. Sadani and J.-W. Chern, Curr. Med. Chem., 24, 622 (2017); https://doi.org/10.2174/0929867323666161129124915
P. Sikka, J.K. Sahu, A.K. Mishra and S.R. Hashim, Med. Chem., 5, 479 (2015); https://doi.org/10.4172/2161-0444.1000305
A.K. Ghosh and M. Brindisi, J. Med. Chem., 63, 2751 (2020); https://doi.org/10.1021/acs.jmedchem.9b01541
J.N. Chen and D.W. Wu, T. Li, K.-J. Yang, L. Cheng, Z.-P. Zhou, S.-M. Pu and W.-H. Lin, Curr. Top. Med. Chem., 17, 3099 (2017); https://doi.org/10.2174/1568026617666170707123553
A. Elkamhawy and A.K. Farag, A.N.I. Viswanath, T.M. Bedair, D.G. Leem, K.-T. Lee, A.N. Pae and E.J. Roh, Bioorg. Med. Chem. Lett., 25, 5147 (2015); https://doi.org/10.1016/j.bmcl.2015.10.003
L. Garuti, M. Roberti, G. Bottegoni and M. Ferraro, Curr. Med. Chem., 23, 1528 (2016); https://doi.org/10.2174/0929867323666160411142532
M. El-Gamal and C.-H. Oh, Bull. Korean Chem. Soc., 33, 1571 (2012); https://doi.org/10.5012/bkcs.2012.33.5.1571
P. Wu, T.E. Nielsen and M.H. Clausen, Trends Pharmacol. Sci., 36, 422 (2015); https://doi.org/10.1016/j.tips.2015.04.005
Y. Aoki and Y. Matsubara, Int. J. Hematol., 97, 30 (2013); https://doi.org/10.1007/s12185-012-1239-y
J. Dietrich, V. Gokhale, X. Wang, L.H. Hurley and G.A. Flynn, Bioorg. Med. Chem., 18, 292 (2010); https://doi.org/10.1016/j.bmc.2009.10.055
M. Hussain, M. Baig, H.S.A. Mohamoud, Z. Ulhaq, D.C. Hoessli, G.S. Khogeer, R.R. Al-Sayed and J.Y. Al-Aama, Saudi J. Biol. Sci., 22, 359 (2015); https://doi.org/10.1016/j.sjbs.2014.10.002
U. Ammar, M. Abdel-Maksoud and C.-H. Oh, Eur. J. Med. Chem., 158, 144 (2018); https://doi.org/10.1016/j.ejmech.2018.09.005
Y. Wang, H. Nie, X. Zhao, Y. Qin and X. Gong, BMC Cancer, 16, 742 (2016); https://doi.org/10.1186/s12885-016-2767-2
M. Kohler, S. Ehrenfeld, S. Halbach, M. Lauinger, U. Burk, N. Reischmann, S. Cheng, C. Spohr, F.M. Uhl, N. Köhler, K. Ringwald, S. Braun, C. Peters, R. Zeiser, T. Reinheckel and T. Brummer, Oncogene, 38, 1324 (2019); https://doi.org/10.1038/s41388-018-0663-8
M. Abdel-Maksoud, M. El-Gamal, M.M. Gamal El-Din and C.H. Oh, J. Enzyme Inhib. Med. Chem., 34, 97 (2019); https://doi.org/10.1080/14756366.2018.1530225
Kaur, P. Kaur, A. Mittal, S.K. Nayak and G.L. Khatik, Asian J. Pharm. Clin. Res., 10, 28 (2017); https://doi.org/10.22159/ajpcr.2017.v10s4.21332
A. El Aissouq, O. Chedadi, M. Bouachrine and A. Ouammou, J. Chem., 2021, 1 (2021); https://doi.org/10.1155/2021/1901484
R. Herowati and G.P. Widodo, Procedia Chem., 13, 63 (2014); https://doi.org/10.1016/j.proche.2014.12.007
S.S. Qawoogha and A. Shahiwala, J. Recept. Signal Transduct. Res., 40, 67 (2020); https://doi.org/10.1080/10799893.2020.1715431
W. Li, X. Zhai, Z. Zhong, G. Li, Y. Pu and P. Gong, Arch. Pharm. Chem. Life Sci., 11, 349 (2011); https://doi.org/10.1002/ardp.201000326
C.S. Lu, K. Tang, Y. Li, B. Jin, D.L. Yin, C. Ma, X.G. Chen and H.H. Huang, Yao Xue Xue Bao, 48, 709 (2013)
X. Kong, Z. Yao, Z. He, W. Xu and J. Yao, MedChemComm, 6, 867 (2015); https://doi.org/10.1039/C4MD00536H
C. Wu, S. Xu, Y. Guo, J. Wu, R. Luo, W. Wang, Y. Tu, Le Chen, W. Zhu and P. Zheng, Med. Chem. Res., 27, 374 (2017); https://doi.org/10.1007/s00044-017-2045-0
B. Moku, L. Ravindar, K.P. Rakesh and H.-L. Qin, Bioorg. Chem., 86, 513 (2019); https://doi.org/10.1016/j.bioorg.2019.02.030