Skip to main content
SpringerLink
Log in

Coumarin-Pyrazole Linked Carbodithioates as Potential Anti-Сancer Agents: Design, Synthesis, Biological, and Molecular Docking Investigation

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of novel benzyl 5-(substitutedphenyl)-3-(2-oxo-2H-chromen-3-yl)-4,5-dihydro-1H-pyrazole-1-carbodithioate were obtained. The anti-cancer activity of synthesised compounds against lung cancer (A-549) and breast cancer cell lines (MDA-MB-231) was investigated by MTT assay. The most of the synthesised compounds were effective against both cancer cell lines and demonstrated significant cytotoxicity. Molecular docking investigation of the synthesised compounds and the cyclin dependent kinase-2 (CDK2) protein revealed that the synthesised compounds displayed greater C-score values, validating the findings.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Scheme
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.
Fig. 10.

Similar content being viewed by others

REFERENCES

  1. Weir, H.K., Anderson, R.N., Coleman King, S.M., Soman, A., Thompson, T.D., Hong, Y., and Moller, B., Prev. Chronic. Dis., 2016, vol. 13, p. E157. https://doi.org/10.5888/pcd13.160211

  2. Vallri, K.K., Nagaraju, P.V.V.S., Viswanath, I.V.K., and Singh, R.V., Russ. J. Org. Chem., 2020, vol. 56, no. 3, p. 524. https://doi.org/10.1134/S1070428020030252

    Article  CAS  Google Scholar 

  3. Siegel, R.L., Miller, K.D., and Jemal, A., CA: A Cancer J. Clin., 2019, vol. 1, p. 7. https://doi.org/10.3322/caac.21551

  4. Bray, F., Ferlay, J., Soerjomataram, I., Siegel, R.L., Torre, L.A., and Jemal, A., CA: Cancer J. Clin., 2018, vol. 68, p. 394. https://doi.org/10.3322/caac.21492

    Article  Google Scholar 

  5. Sung, H., Ferlay, J., Siegel, R.L., Laversanne, M., Soerjomataram, I., Jemal, A., and Bray F., CA: Cancer J. Clin., 2021, vol. 71, p. 209. https://doi.org/10.3322/caac.21660

  6. Zhang, J., Zhang, Z., Yang, B., Jing, X., Zhong, W., and Tang, H., Lat. Am. J. Pharm., 2016, vol. 35, p. 1719

    CAS  Google Scholar 

  7. Koleckar, V., Kubikova, K., Rehakova, Z., Kuca, K., Jun, D., Jahodar, L., and Opletal, L., Med. Chem., 2008, vol. 8, p. 436. https://doi.org/10.2174/138955708784223486

    Article  CAS  Google Scholar 

  8. Dholaria, B., Hammond, W., Shreders, A., and Lou, Y., J. Hematol. Oncol., 2016, vol. 9, p. 138. https://doi.org/10.1186/s13045-016-0365-z

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Hirsch, F.R., Scagliotti, G.V., Mulshine, J.L., Kwon, R., Curran, W.J., Wu, and Y.L., Paz-Ares, L., The Lancet., 2017, vol. 389, p. 299. https://doi.org/10.1016/S0140-6736(16)30958-8

  10. Wood, S.L., Pernemalm, M., Crosbie, P.A., and Whetton, A.D., Cancer Treat. Rev., 2015, vol. 41, p. 361. https://doi.org/10.1016/j.ctrv.2015.02.008

    Article  CAS  PubMed  Google Scholar 

  11. Hill, A., Gotham, D., Fortunak, J., Meldrum, J., Erbacher, I., Martin, M., Shoman, H., Levi, J., Powderly, W.G., and Bower, M., BMJ Open., 2016, vol. 6, p. e009586-e009594. https://doi.org/10.1136/bmjopen-2015-009586

  12. Zakowsky, M.F., Cancer Cytopathol., 2017, vol. 125, p. 470. https://doi.org/10.1002/cncy.21866

    Article  Google Scholar 

  13. Sun, J.M., Hwang, D.W., Ahn, J.S., Ahn, M.J., and Park, K., Plos One., 2013, vol. 8, p. e64816-e64823. https://doi.org/10.1371/journal.pone.0064816

  14. Gridelli, C. and Sacco, P.C., Curr. Opin. Oncol., 2016, vol. 28, p. 110. https://doi.org/10.1097/CCO.0000000000000266

    Article  CAS  PubMed  Google Scholar 

  15. Gronberg, B.H., Sundstrom, S., Kaasa, S., Bremnes, R.M., Flotten, O., Amundsen, T., Hjelde, H.H., Plessen, C., and Jordhoy, M., Eur. J. Cancer., 2010, vol. 46, p. 2225. https://doi.org/10.1016/j.ejca.2010.04.009

    Article  CAS  PubMed  Google Scholar 

  16. Yang, L., Zhou, Y., Li, Y., Zhou, J., Wu, Y., Cui, Y., Yang, G., and Hong, Y., Cancer Lett., 2015, vol. 357, p. 520. https://doi.org/10.1016/j.canlet.2014.12.003

    Article  CAS  PubMed  Google Scholar 

  17. Akki, M., Reddy, D.S., Katagi, K.S., Kumar, A., Devarajegowda, H.C., Sunitha Kumari, M., Babagond, V., Mane, S., and Joshi, S. D., J. Mol. Struct., 2022, vol. 1266, p. 133452. https://doi.org/10.1016/j.molstruc.2022.133452

    Article  CAS  Google Scholar 

  18. Krishna, C., Bhargavi, M.V., Rao, Y.J., and Krupadanam, G.L.D., Russ. J. Gen. Chem., 2017, vol. 87, p. 1857. https://doi.org/10.1134/S1070363217080345

  19. Reddy, D.S., Hosamani, K.M., Devarajegowda, H.C., and Kurjogi, M.M., RSC Adv., 2015, vol. 5, p. 64566. https://doi.org/10.1039/C5RA09508E

    Article  CAS  Google Scholar 

  20. Peng, X.M., Damu, G.L.V., and Zhou, C.H., Curr. Pharm. Des., 2013, vol. 19, p. 3884. https://doi.org/10.2174/1381612811319210013

    Article  CAS  PubMed  Google Scholar 

  21. Morita, H., Dota,T., and Kobayashi J., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3665. https://doi.org/10.1016/j.bmcl.2004.05.015

  22. Meggio, F., Pagano, M.A., Moro, S., Zagotto, G., Ruzzene, M., Sarno, S., Cozza, G., Bain, J., Elliott, M., Donella-Deana, A., Brunati, A.M., and Pinna, L.A., Biochemistry, 2004, vol. 43, p. 12931, https://doi.org/10.1021/bi048999g

    Article  CAS  PubMed  Google Scholar 

  23. Wu, X.-Q., Huang, C., Jia, Y.-M., Song, B.-A., Li, J., and Liu, X.-H., Eur. J. Med. Chem., 2014, vol. 74, p. 717. https://doi.org/10.1016/j.ejmech.2013.06.014

    Article  CAS  PubMed  Google Scholar 

  24. Chen, Y., Liu, H.R., Liu, H.S., Cheng, M., Xia, P., Qian, K., Wu, P.C., Lai, C.Y., Xia, Y., Yang, Z.Y., MorrisNatschke, S.L., and Lee, K.H., Eur. J. Med. Chem., 2012, vol. 49, p. 74. https://doi.org/10.1016/j.ejmech.2011.12.025

    Article  CAS  PubMed  Google Scholar 

  25. Chu, C.Y., Tsai, Y.Y., Wang, C.J., Lin, W.L., and Tseng, T.H., Eur. J. Pharmacol., 2001, vol. 416, p. 25. https://doi.org/10.1016/s0014-2999(01)00859-7

  26. Ruiz, M.C., Chilpa, R.R., Estrada, E., Reyes, E.J., Fariña, G.G., and Fragoso, L.R.J., J. Pharm. Pharmacol., 2007, vol. 59, p. 719. https://doi.org/10.1211/jpp.59.5.0013

    Article  CAS  Google Scholar 

  27. Bras, G.L., Radanyi, C., Peyrat, J.F., Brion, J.D., Alami, M., Marsaud, V., Stella, B., and Renoir, J.M., J. Med. Chem., 2007, vol. 50, p. 6189. https://doi.org/10.1021/jm0707774

  28. Donnelly, A.C., Mays, J.R., Burlison, J.A., Nelson, J.T., Vielhauer, G., Holzbeierlein, J., and Blagg, B.S.J., J. Org. Chem., 2008, vol. 73, p. 8901. https://doi.org/10.1021/jo801312r

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Dong, Y., Shi, Q., Liu, Y.-N., Wang, X., Bastow, K.F., and Lee, K.-H., J. Med. Chem., 2009, vol. 52, p. 3586. https://doi.org/10.1021/jm9001567

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Wang, X., Nakagawa-Goto, K., Bastow, K.F., Don, M.J., Lin, Y.-L., Wu, T-S., and Lee, K.-H., J. Med. Chem., 2006, vol. 49, p. 5631. https://doi.org/10.1021/jm060184d

  31. Stanway, S.J., Purohit, A., Woo, L.W., Sufi, S., Vigushin, D., Ward, R., Wilson, R.H., Stanczyk, F.Z., Dobbs, N., Kulinskaya, E., Elliott, M., Potter, B.V., Reed, M.J., and Coombes, R.C., Clin. Cancer Res., 2006, vol. 12, p. 1585. https://doi.org/10.1158/1078-0432.CCR-05-1996

    Article  CAS  PubMed  Google Scholar 

  32. Xu, X., Zhang, Y., Qu, D., Jiang, T., and Li, S., J. Exp. Clin. Cancer Res., 2011, vol. 30, p. 30. https://doi.org/10.1186/1756-9966-30-33

    Article  CAS  Google Scholar 

  33. Zhang, W., Li, Z., Zhou, M., Wu, F., Hou, X., Luo, H., Liu, H., Han, X., Yan, G., Ding, Z., and Li, R., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 799. https://doi.org/10.1016/j.bmcl.2013.12.095

  34. Ragavan, R.V., Vijayakumar, V., and Kumari, N.S., Pharmacol. Online, 2011, vol. 3, p. 1348

  35. Tewari, A.K. and Mishra, A., Bioorg. Med. Chem., 2001, vol. 9, p. 715. https://doi.org/10.1016/s0968-0896(00)00285-6

    Article  CAS  PubMed  Google Scholar 

  36. El Shehry, M.F., Ewies, E.F. and Zayed, E.M., Russ. J. Gen. Chem., 2019, vol. 89, p. 492. https://doi.org/10.1134/S1070363219030216

    Article  CAS  Google Scholar 

  37. Venkatesh, N., Sundergoud, S., Swamy, M.K., and Veerasomaiah, P., Russ. J. Org. Chem., 2020, vol. 56, p. 1635. https://doi.org/10.1134/S1070428020090213

    Article  CAS  Google Scholar 

  38. Perez, A.G., Wester, R.T., Allen, M.C., Brown, J.A., Buchholz, A.R., Cook, E.R., Day, W.W., Hamanaka, E.S., Kennedy, S.P., Knight, D.R., Kowalczyk, P.J., Marala, R.B., Mularski, C.J., Novomisle, W.A., Ruggeri, R.B., Tracey, W.R., and Hill, R., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 803. https://doi.org/10.1016/S0960-894X(01)00059-2

  39. Reddy, K.I., Aruna, C., Manisha, M., Srihari, K., Babu, K.S., Vijayakumar, V., Sarveswari, S., Priya, R., Amrita, A., and Siva, R., J. Photochem. Photobiol. B, 2017, vol. 168, p. 89. https://doi.org/10.1016/j.jphotobiol.2017.02.003

    Article  CAS  Google Scholar 

  40. Camper, N.D., Gum, J.M., Lyles, D.E., Pennington, W.T., Beam, C.F., and Metz, C.R., J. S. C. Acad. Sci., 2017, vol. 15, p. 27.

    Google Scholar 

  41. Brighton, D., Johnston, S.R.D., and Wood, M., The Royal Marsden Hospital Handbook of Cancer Chemotherapy: A Guide for the Multidisciplinary Team, London: Elsevier Churchill Livingstone, 2005, p. 1–17

  42. Reddy, T.S., Kulhari, V.H., Reddy, G., Bansal, V., Kamal, A., and Shukla, R., Eur. J. Med. Chem., 2015, vol. 101, p. 790. https://doi.org/10.1016/j.ejmech.2015.07.031

    Article  CAS  PubMed  Google Scholar 

  43. Swanepoel, B., Nitulescu, G.M., Olaru, O.T., Venables, L., and Venter, M.V.D., Int. J. Mol. Sci., 2019, vol. 20, p. 5559. https://doi.org/10.3390/ijms20225559

  44. Schenone, S., Bruno, O., Ranise, A., Bondavalli, F., Brullo, C., Fossa, P., Mosti, L., Menozzi, G., Carraro, F., Naldini, A., Bernini, C., Manetti, F., and Botta, M., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 2511. https://doi.org/10.1016/j.bmcl.2004.03.013

  45. Manetti, F., Brullo, C., Magnani, M., Mosci, F., Chelli, B., Crespan, E., Schenone, S., Naldini, A., Bruno, O., Trincavelli, M. L., Maga, G., Carraro, F., Martini, C., Bondavalli, F., and Botta, M., J. Med. Chem., 2008, vol. 51, p. 1252. https://doi.org/10.1021/jm701240c

  46. Huang, S., Lin, R., Yu, Y., Lu, Y., Connolly, P.J., Chiu, G., Li, S., Emanuel, S.L., and Middleton, S.A., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 1243. https://doi.org/10.1016/j.bmcl.2006.12.031

    Article  CAS  PubMed  Google Scholar 

  47. Maciejewska, N., Olszewski, M., Jurasz, J., Serocki, M., Dzierzynska, M., Cekala, K., Wieczerzak, E., and Baginski, M., Scientific reports., 2022, vol. 12, p. 3703. https://doi.org/10.1038/s41598-022-07691-6

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Farag, A.M., Mayhoub, A.S., Eldebss, T.M.A., Amr, A.-G.E., Ali, K.A.K., Abdel-Hafez, N.A., and Abdulla, M.M., Arch. Pharm. Chem. Life Sci.., 2010, vol. 343, p. 384. https://doi.org/10.1002/ardp.200900176

  49. Husseiny, E.M., Bioorg. Chem., 2020, vol. 102, p. 104053. https://doi.org/10.1016/j.bioorg.2020.104053

    Article  CAS  PubMed  Google Scholar 

  50. Farag, A.M., Ali, K.A.K., El-Debss, T.M.A., Mayhoub, A.S., Amr, A.E., Abdel-Hafez, N.A., and Abdulla, M.M., Eur. J. Med. Chem., 2010, vol. 45, p. 5887. https://doi.org/10.1016/j.ejmech.2010.09.054

  51. Shi, J.B., Tang, W.J., Bao, Qi.X., Li, J., Li, R., and Liu, X.H., Eur. J. Med. Chem., 2015, vol. 90, p. 889. https://doi.org/10.1016/j.ejmech.2014.12.013

    Article  CAS  PubMed  Google Scholar 

  52. Hassan, A.S., Moustafa, G.O., Awad, H.M., Nossier, E.S., and Mady, M.F., ACS Omega., 2021, vol. 6, p. 12361. https://doi.org/10.1021/acsomega.1c01604

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Gupta, J.K., Sharma, P.K., Dudhe, R., Chaudhary, A., Singh, A., Verma, P.K., Mondal, S.C., Yadav, R.K., and Kashyap, S., Med. Chem. Res., 2012, vol. 21, p. 1625. https://doi.org/10.1007/s00044-011-9675-4

    Article  CAS  Google Scholar 

  54. Ali, M.A., and Tarajder, M.T.H., J. Inorg. Nucl. Chem., 1977, vol. 39, p. 1785. https://doi.org/10.1016/0022-1902(77)80202-9

  55. Manosroi, J., Dhumtanom, P., and Manosroi, A., Cancer Lett., 2006, vol. 235, p. 114. https://doi.org/10.1016/j.canlet.2005.04.021

    Article  CAS  PubMed  Google Scholar 

  56. Singh, V.K., Kadu, R., and Roy, H., Eur. J. Med. Chem., 2014, vol. 74, p. 552. https://doi.org/10.1016/j.ejmech.2013.12.035

    Article  CAS  PubMed  Google Scholar 

  57. Babić, S., Horvat, A.J., Pavlović, D.M., and Kaštelan-Macan, M., Trends Anal. Chem., 2007, vol. 26, p. 1043. https://doi.org/10.1016/j.trac.2007.09.004

    Article  CAS  Google Scholar 

  58. Reddy, D.S., Kongot, M., Singh, V., Maurya, N., Patel, R., Singhal, N.K., Avecilla, F., and Kumar, A., Bioorg. Chem., 2019, vol. 92, p. 103212. https://doi.org/10.1016/j.bioorg.2019.103212

    Article  CAS  PubMed  Google Scholar 

  59. Manallack, D.T., Prankerd, R.J., Yuriev, E., Oprea, T.I., and Chalmers, D. K., Chem. Soc. Rev., 2013, vol. 42, p. 485. https://doi.org/10.1039/C2CS35348B

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  60. Fischer, H., Gottschlich, R., and Seelig, A., J. Membr. Biol., 1998, vol. 165, p. 201. https://doi.org/10.1007/s002329900434

    Article  CAS  PubMed  Google Scholar 

  61. Gasteiger, J., and Marsili, M., Tetrahedron,1980, vol. 36, p. 3219. https://doi.org/10.1016/0040-4020(80)80168-2

  62. Tripos International Sybyl-X 2.0, Tripos International, St. Louis, MO, USA. 2012.

Download references

ACKNOWLEDGMENTS

The authors acknowledge the Department of Chemistry, Karnatak University’s Karnatak Science College, Dharwad and Seed money grant KUD for enabling research facilities. The authors would also like to acknowledge the SAIF and the Karnatak University Scientific Instrument Centre for their technical assistance for this investigation.

Author information

Authors and Affiliations

  1. Department of Chemistry, Karnatak University’s Karnatak Science College, 580001, Dharwad, India

    M. Akki, K. S. Katagi & V. Babagond

  2. Centre for Nano and Material Sciences, Jain University, 562112, Bangalore, India

    D. S. Reddy & A. Kumar

  3. Department of Chemistry, KLS Vishwanathrao Deshpande Institute of Technology, 590018, Haliyal, India

    R. S. Munnolli

  4. Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, S.E.T.’s College of Pharmacy, SR Nagar, 580002, Dharwad, India

    S. D. Joshi

Authors
  1. M. Akki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. S. Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. S. Katagi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. Babagond
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. R. S. Munnolli
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. D. Joshi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. S. Katagi.

Ethics declarations

The authors declare no conflict of interest.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Akki, M., Reddy, D.S., Katagi, K.S. et al. Coumarin-Pyrazole Linked Carbodithioates as Potential Anti-Сancer Agents: Design, Synthesis, Biological, and Molecular Docking Investigation. Russ J Gen Chem 92, 2092–2107 (2022). https://doi.org/10.1134/S1070363222100231

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222100231

Keywords:

Search

Navigation