Copyright (c) 2024 Kishore Ravada, Sreenivas sunkara, Durga prasad Baka, Praveen Kumar Edigi, , Leela Prasad Yandrati, Swamy Sekhar Kaladi, Sai Prasad Gedam
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Novel Quinoline containing 1,2,3-Triazole Hybrids: Evaluation of Anticancer Activity and Molecular Docking Studies
Corresponding Author(s) : Sreenivas Sunkara
Asian Journal of Chemistry,
Vol. 36 No. 11 (2024): Vol 36 Issue 11, 2024
Abstract
Newscaffolds consists of 1,2,3-triazole linked quinoline derivatives (9a-l) were synthesized and confirmed by 1H NMR, 13C NMR and ESI-MS spectra. Using the MTT assay and doxorubicin as the standard dugs, all the synthesized compounds were further investigated for their anticancer efficacy against the two cancer cell lines, HT-1080 and A-549. When compared to doxorubicin, compounds 9c, 9j and 9d showed the strongest efficacy against the tested cancer cell lines, HT-1080 and A-549. Using the PyRx tool’s Autodock Vina, the molecular docking investigations on enoyl reductase were carried out. It is interesting to note that the interactions and binding energies determined by docking molecules match the data under investigation.
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- D. Hanahan and R.A. Weinberg, Cell, 144, 646 (2011); https://doi.org/10.1016/j.cell.2011.02.013
- S.B. Baylin and P.A. Jones, Cold Spring Harb. Perspect. Biol., 8, 019505 (2016); https://doi.org/10.1101/cshperspect.a019505
- K. Ando, Q. Hu, Y. Kasagi, E. Oki and M. Mori, Ann. Gastroenterol. Surg., 5, 419 (2021); https://doi.org/10.1002/ags3.12440
- A. Erguc, M.D. Altintop, O. Atli, B. Sever, G. Iscan, G. Gormus and A. Ozdemir, Lett. Drug Design Discov., 15, 193 (2018); https://doi.org/10.2174/1570180814666171003145227
- K.D. Upadhyay, N.M. Dodia, R.C. Khunt, R.S. Chaniara and A.K. Shah, ACS Med. Chem. Lett., 9, 283 (2018); https://doi.org/10.1021/acsmedchemlett.7b00545
- R. Cannalire, M.L. Barreca, G. Manfroni and V. Cecchetti, J. Med. Chem., 59, 16 (2016); https://doi.org/10.1021/acs.jmedchem.5b00825
- Y.L. Fan, J.B. Wu, X.W. Cheng, F.Z. Zhang and L.S. Feng, Eur. J. Med. Chem., 146, 554 (2018); https://doi.org/10.1016/j.ejmech.2018.01.080
- S. Zhang, Z. Xu, C. Gao, Q.C. Ren, L. Chang, Z.S. Lv and L.S. Feng, Eur. J. Med. Chem., 138, 501 (2017); https://doi.org/10.1016/j.ejmech.2017.06.051
- Z. Xu, S. Zhang, C. Gao, J. Fan, F. Zhao, Z.-S. Lv and L.-S. Feng, Chin. Chem. Lett., 28, 159 (2017); https://doi.org/10.1016/j.cclet.2016.07.032
- Y.Q. Hu, C. Gao, S. Zhang, L. Xu, Z. Xu, L.S. Feng, X. Wu and F. Zhao, Eur. J. Med. Chem., 139, 22 (2017); https://doi.org/10.1016/j.ejmech.2017.07.061
- Y.L. Fan, X.W. Cheng, J.B. Wu, M. Liu, F.Z. Zhang, Z. Xu and L.S. Feng, Eur. J. Med. Chem., 146, 1 (2018); https://doi.org/10.1016/j.ejmech.2018.01.039
- K.C. Sekgota, S. Majumder, M. Isaacs, D. Mnkandhla, H.C. Hoppe, S.D. Khanye, F.H. Kriel, J. Coates and P.T. Kaye, Bioorg. Chem., 75, 310 (2017); https://doi.org/10.1016/j.bioorg.2017.09.015
- Z.G. Luo, J.J. Tan, Y. Zeng, C.X. Wang and L.M. Hu, Mini Rev. Med. Chem., 10, 1046 (2010); https://doi.org/10.2174/1389557511009011046
- N.J.P. Subhashini, E.P. Kumar, N. Gurrapu and V. Yerragunta, J. Mol. Struct., 1180, 618 (2019); https://doi.org/10.1016/j.molstruc.2018.11.029
- R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E.D. Clercq, C.-F. Perno, A. Karlsson, J. Balzarini and M.J. Camarasa, J. Med. Chem., 37, 4185 (1994); https://doi.org/10.1021/jm00050a015
- E. Praveenkumar, N. Gurrapu, P. Kumar Kolluri, V. Yerragunta, B.R. Kunduru and N.J.P. Subhashini, Bioorg. Chem., 90, 103056 (2019); https://doi.org/10.1016/j.bioorg.2019.103056
- M.T. Pasko, S.C. Piscitelli and A.D. Van Slooten, Ann. Pharmacother., 24, 860 (1990); https://doi.org/10.1177/106002809002400914
- E. Praveenkumar, N. Gurrapu, P.K. Kolluri, Shivaraj, N.J.P. Subhashini and A. Dokala, Bioorg. Chem., 116, 105377 (2021); https://doi.org/10.1016/j.bioorg.2021.105377
- N. Gurrapu, E.P. Kumar, P.K. Kolluri, S. Putta, S.K. Sivan and N.J.P. Subhashini, J. Mol. Struct., 1217, 128356 (2020); https://doi.org/10.1016/j.molstruc.2020.128356
- S. Rajan, S. Puri, D. Kumar, M.H. Babu, K. Shankar, S. Varshney, A. Srivastava, A. Gupta, M.S. Reddy and A.N. Gaikwad, Eur. J. Med. Chem., 143, 1345 (2018); https://doi.org/10.1016/j.ejmech.2017.10.034
- D.S. Alshaya, R.M.O. Tawakul, I. Zaki, A.H. Abu Almaaty, E. Fayad and Y.M. Abd El-Aziz, RSC Adv., 13, 23538 (2023); https://doi.org/10.1039/D3RA03849A
- Y. Rose, J.M. Duarte, R. Lowe, J. Segura, C. Bi, C. Bhikadiya, L. Chen, A.S.S. Rose, S.K. Bittrich, Burley and J.D. Westbrook, J. Mol. Biol., 433, 166704 (2021); https://doi.org/10.1016/j.jmb.2020.11.003
- G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner and R.K. Belew, J. Comput. Chem., 30, 2785 (2009); https://doi.org/10.1002/jcc.21256
- S. Dallakyan and A.J. Olson, Methods Mol. Biol., 1263, 243 (2015); https://doi.org/10.1007/978-1-4939-2269-7_19
- B.H. Mooers, Protein Sci., 29, 268 (2020); https://doi.org/10.1002/pro.3781
- M.J. Stewart, S. Parikh, G. Xiao, P.J. Tonge and C. Kisker, J. Mol. Biol., 290, 859 (1999); https://doi.org/10.1006/jmbi.1999.2907
- R.J. Heath and C.O. Rock, J. Biol. Chem., 270, 26538 (1995); https://doi.org/10.1074/jbc.270.44.26538
- R. Massengo-Tiassé and J.E. Cronan, Cell. Mol. Life Sci., 66, 1507 (2009); https://doi.org/10.1007/s00018-009-8704-7
References
D. Hanahan and R.A. Weinberg, Cell, 144, 646 (2011); https://doi.org/10.1016/j.cell.2011.02.013
S.B. Baylin and P.A. Jones, Cold Spring Harb. Perspect. Biol., 8, 019505 (2016); https://doi.org/10.1101/cshperspect.a019505
K. Ando, Q. Hu, Y. Kasagi, E. Oki and M. Mori, Ann. Gastroenterol. Surg., 5, 419 (2021); https://doi.org/10.1002/ags3.12440
A. Erguc, M.D. Altintop, O. Atli, B. Sever, G. Iscan, G. Gormus and A. Ozdemir, Lett. Drug Design Discov., 15, 193 (2018); https://doi.org/10.2174/1570180814666171003145227
K.D. Upadhyay, N.M. Dodia, R.C. Khunt, R.S. Chaniara and A.K. Shah, ACS Med. Chem. Lett., 9, 283 (2018); https://doi.org/10.1021/acsmedchemlett.7b00545
R. Cannalire, M.L. Barreca, G. Manfroni and V. Cecchetti, J. Med. Chem., 59, 16 (2016); https://doi.org/10.1021/acs.jmedchem.5b00825
Y.L. Fan, J.B. Wu, X.W. Cheng, F.Z. Zhang and L.S. Feng, Eur. J. Med. Chem., 146, 554 (2018); https://doi.org/10.1016/j.ejmech.2018.01.080
S. Zhang, Z. Xu, C. Gao, Q.C. Ren, L. Chang, Z.S. Lv and L.S. Feng, Eur. J. Med. Chem., 138, 501 (2017); https://doi.org/10.1016/j.ejmech.2017.06.051
Z. Xu, S. Zhang, C. Gao, J. Fan, F. Zhao, Z.-S. Lv and L.-S. Feng, Chin. Chem. Lett., 28, 159 (2017); https://doi.org/10.1016/j.cclet.2016.07.032
Y.Q. Hu, C. Gao, S. Zhang, L. Xu, Z. Xu, L.S. Feng, X. Wu and F. Zhao, Eur. J. Med. Chem., 139, 22 (2017); https://doi.org/10.1016/j.ejmech.2017.07.061
Y.L. Fan, X.W. Cheng, J.B. Wu, M. Liu, F.Z. Zhang, Z. Xu and L.S. Feng, Eur. J. Med. Chem., 146, 1 (2018); https://doi.org/10.1016/j.ejmech.2018.01.039
K.C. Sekgota, S. Majumder, M. Isaacs, D. Mnkandhla, H.C. Hoppe, S.D. Khanye, F.H. Kriel, J. Coates and P.T. Kaye, Bioorg. Chem., 75, 310 (2017); https://doi.org/10.1016/j.bioorg.2017.09.015
Z.G. Luo, J.J. Tan, Y. Zeng, C.X. Wang and L.M. Hu, Mini Rev. Med. Chem., 10, 1046 (2010); https://doi.org/10.2174/1389557511009011046
N.J.P. Subhashini, E.P. Kumar, N. Gurrapu and V. Yerragunta, J. Mol. Struct., 1180, 618 (2019); https://doi.org/10.1016/j.molstruc.2018.11.029
R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E.D. Clercq, C.-F. Perno, A. Karlsson, J. Balzarini and M.J. Camarasa, J. Med. Chem., 37, 4185 (1994); https://doi.org/10.1021/jm00050a015
E. Praveenkumar, N. Gurrapu, P. Kumar Kolluri, V. Yerragunta, B.R. Kunduru and N.J.P. Subhashini, Bioorg. Chem., 90, 103056 (2019); https://doi.org/10.1016/j.bioorg.2019.103056
M.T. Pasko, S.C. Piscitelli and A.D. Van Slooten, Ann. Pharmacother., 24, 860 (1990); https://doi.org/10.1177/106002809002400914
E. Praveenkumar, N. Gurrapu, P.K. Kolluri, Shivaraj, N.J.P. Subhashini and A. Dokala, Bioorg. Chem., 116, 105377 (2021); https://doi.org/10.1016/j.bioorg.2021.105377
N. Gurrapu, E.P. Kumar, P.K. Kolluri, S. Putta, S.K. Sivan and N.J.P. Subhashini, J. Mol. Struct., 1217, 128356 (2020); https://doi.org/10.1016/j.molstruc.2020.128356
S. Rajan, S. Puri, D. Kumar, M.H. Babu, K. Shankar, S. Varshney, A. Srivastava, A. Gupta, M.S. Reddy and A.N. Gaikwad, Eur. J. Med. Chem., 143, 1345 (2018); https://doi.org/10.1016/j.ejmech.2017.10.034
D.S. Alshaya, R.M.O. Tawakul, I. Zaki, A.H. Abu Almaaty, E. Fayad and Y.M. Abd El-Aziz, RSC Adv., 13, 23538 (2023); https://doi.org/10.1039/D3RA03849A
Y. Rose, J.M. Duarte, R. Lowe, J. Segura, C. Bi, C. Bhikadiya, L. Chen, A.S.S. Rose, S.K. Bittrich, Burley and J.D. Westbrook, J. Mol. Biol., 433, 166704 (2021); https://doi.org/10.1016/j.jmb.2020.11.003
G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner and R.K. Belew, J. Comput. Chem., 30, 2785 (2009); https://doi.org/10.1002/jcc.21256
S. Dallakyan and A.J. Olson, Methods Mol. Biol., 1263, 243 (2015); https://doi.org/10.1007/978-1-4939-2269-7_19
B.H. Mooers, Protein Sci., 29, 268 (2020); https://doi.org/10.1002/pro.3781
M.J. Stewart, S. Parikh, G. Xiao, P.J. Tonge and C. Kisker, J. Mol. Biol., 290, 859 (1999); https://doi.org/10.1006/jmbi.1999.2907
R.J. Heath and C.O. Rock, J. Biol. Chem., 270, 26538 (1995); https://doi.org/10.1074/jbc.270.44.26538
R. Massengo-Tiassé and J.E. Cronan, Cell. Mol. Life Sci., 66, 1507 (2009); https://doi.org/10.1007/s00018-009-8704-7