Skip to main content
Log in

Synthesis, Characterization of Novel Thiazole Hydrazine Derivatives, and Inhibitory Action Against the VEGFR-2

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

Abstract

Objective: Synthesis, characterization of novel thiazole hydrazine derivatives and inhibitory action against the VEGFR-2. Methods: The novel synthesized derivatives were appraised for their ability to inhibit the growth of cancer cells in vitro utilizing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay method. Results and Discussion: The synthesized derivatives divulge moderate to noteworthy in vitro anticancer activity towards the chosen cancer cell lines. Compounds (Va), (Vb), and (Ve) exhibited prominent anticancer activities with IC50 values 10.24–15.44 µM. Conclusions: Amongst these, compound (Va), (Vb), and (Ve) showed the most potent inhibition when compared with other tested compounds. Thus, the reports obtained of the current studies divulge that the thiazole hydrazine derivatives can be developed as auspicious anticancer entities in future.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1.

Similar content being viewed by others

DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

REFERENCES

  1. Nagle, D.G., Zhou, Y.D., Park, P.U., Paul, V.J., Rajbhandari, I., Duncan, C.J.G., and Pasco, D.S., J. Nat. Prod., 2000, vol. 63, pp. 1431–1433. https://doi.org/10.1021/np000216e

    Article  CAS  PubMed  Google Scholar 

  2. Cossy, J., Bellotti, D., and Maguer, A., Synlett, 2003, vol. 10, pp. 1515–1517. https://doi.org/10.1055/s-2003-40868

    Article  Google Scholar 

  3. Yu, H., Kim, I.J., Folk, J.E., Tian, X., Rothman, R.B., Baumann, M.H., Dersch, C.M., Flippen-Anderson, J.L., Parrish, D., Jacobson, A.E., and Rice, K.C., J. Med. Chem., 2004, vol. 47, pp. 2624–2634. https://doi.org/10.1021/jm0305873

    Article  CAS  PubMed  Google Scholar 

  4. Chhabria, M.T., Patel, Modi, P., and Brahmkshatriya, P.S., Curr. Top. Med. Chem., 2016, vol. 26, pp. 2841–2862. https://doi.org/10.2174/1568026616666160506130731

    Article  CAS  Google Scholar 

  5. Kohler, O. and Seitz, O., Chem. Commun., 2003, pp. 2938–2939. https://doi.org/10.1039/b308299g

  6. Singh, I.P., Gupta, S., and Kumar, S., Med. Chem., 2020, vol. 16, pp. 4–23. https://doi.org/10.2174/1573406415666190614101253

    Article  CAS  PubMed  Google Scholar 

  7. Proudfoot, J.S., Patel, U.R., Kapadia, S.R., and Hargrave, K.D., J. Med. Chem., 1995, vol. 38, pp. 1406–1410. https://doi.org/10.1021/jm00008a019

    Article  CAS  PubMed  Google Scholar 

  8. Pansare, D.N., Shelke, R.N., Khade, M.C., Jadhav, V.N., Pawar, C.D., Jadhav, R.A., and Bembalkar, S.R., Eur. Chem. Bull., 2019, vol. 8, pp. 7–14. https://doi.org/10.17628/ecb.2019.8.7-14

    Article  CAS  Google Scholar 

  9. Bai, R., Covell, D.G., Taylor, G.F., Kepler, J.A., Copeland, T.D., Nguyen, N.Y., Pettit, G.R., and Hamel, E., J. Bio. Chem., 2004, vol. 279, pp. 30731–30740. https://doi.org/10.1074/jbc.M402110200

    Article  CAS  Google Scholar 

  10. Brantley, E., Patel, V., Stinson, S.F., Trapani, V., Hose, C.D., Ciolino, H.P., Yeh, G.C., Gutkind, J.S., Sausville, E.A., and Loaiza-Perez, A.I., Anticancer Drugs, 2005, vol. 16, pp. 137–143. https://journals.lww.com/anti-cancerdrugs/abstract/2005/

    Article  CAS  PubMed  Google Scholar 

  11. Patchett, A.A. and Nargund, R.P., Ann. Rep. Med. Chem., 2000, vol. 35, pp. 289–298. https://doi.org/10.1016/S0065-7743(00)35027-8

    Article  CAS  Google Scholar 

  12. Hu, Y. and Bajorath, J., J. Chem. Inf. Model, 2010, vol. 50, pp. 500–510. https://doi.org/10.1021/ci100059q

    Article  CAS  PubMed  Google Scholar 

  13. Patt, W.C., Hamilton, H.W., Taylor, M.D., Ryan, M.J., Taylor, D.G. Jr, Connolly, C.J.C, Doherty, A.M., Klutchko, S.R., Sircar, I., Steinbaugh, B.A., Batley, B.L., Painchaud, C.A., Rapundalo, S.T., Michniewicz, B.M., and Olson, S.C.J., J. Med. Chem., 1992, vol. 35, pp. 2562–2572. https://doi.org/10.1021/jm00092a006

    Article  CAS  PubMed  Google Scholar 

  14. Gomha, S.M. and Abdel-Aziz, H.A., Bull. Korean. Chem. Soc., 2012, vol. 33, pp. 2985–2990. https://doi.org/10.5012/bkcs.2012.33.9.2985

    Article  CAS  Google Scholar 

  15. Karegoudar, P., Karthikeyan, M.S., Prasad, D.J., Mahalinga, M., Holla, B.S., and Kumari, N.S., Eur. J. Med. Chem., 2008, vol. 43, pp. 261–267. https://doi.org/10.1016/j.ejmech.2007.03.014

    Article  CAS  PubMed  Google Scholar 

  16. Cukurovali, A., Yilmaz, I., Gur, S., and Kazaz, C., Eur. J. Med. Chem., 2006, vol. 41, pp. 201–207. https://doi.org/10.1016/j.ejmech.2005.01.013

    Article  CAS  PubMed  Google Scholar 

  17. Sharma, P.K., Sawhney, S.N., Gupta, A., Singh, G.B., and Bani, S., Indian J. Chem., 1998, vol. 37B, pp. 376–381. https://nopr.niscpr.res.in/bitstream/123456789/56779/1/IJCB%2037B%284%29%20376-381.pdf

    Google Scholar 

  18. Shih, M.H. and Ying, K.F., Bioorg. Med. Chem., 2004, vol. 12, pp. 4633–4643. https://doi.org/10.1016/j.bmc.2004.06.033

    Article  CAS  PubMed  Google Scholar 

  19. Shiradkar, M., Kumar, G.V.S., Dasari, V., Tatikonda, S., Akula, K.C., and Shah, R., Eur. J. Med. Chem., 2007, vol. 42, pp. 807–816. https://doi.org/10.1016/j.ejmech.2006.12.001

    Article  CAS  PubMed  Google Scholar 

  20. Gomha, S.M. and Khalil, K.D., Molecules, 2012, vol. 17, pp. 9335–9347. https://doi.org/10.3390/molecules17089335

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Gomha, S.M., Salah, T.A., and Abdelhamid, A.O., Monatsh. Chem., 2015, vol. 146, pp. 149–158. https://doi.org/10.1007/s00706-014-1303-9

    Article  CAS  Google Scholar 

  22. Gomha, S.M., Riyadh, S.M., Abbas, I.M., and Bauomi, M.A., Heterocycles, 2013, vol. 87, pp. 341–356. https://doi.org/10.3987/COM-12-12625

    Article  CAS  Google Scholar 

  23. Pawar, C.D., Sarkate, A.P., Karnik, K.S., and Shinde, D.B., J. Het. Chem., 2018, vol. 55, pp. 1695–1701. https://doi.org/10.1002/jhet.3206

    Article  CAS  Google Scholar 

  24. Chavan, P.N., Pansare, D.N., and Shelke, R.N., J. Chin. Chem. Soc., 2019, vol. 66, pp. 822–828. https://doi.org/10.1002/jccs.201800411

    Article  CAS  Google Scholar 

  25. Sarkate, A.P., Pansare, D.N., Karnik, K.S., Kale, I.A., Bahekar, S.S., and Shinde, D.B., Curr. Micro. Chem., 2017, vol. 4, pp. 163–167. https://doi.org/10.2174/2213335603666161017120230

    Article  CAS  Google Scholar 

  26. Shelke, R.N., Pansare, D.N., and Pawar, C.D., Eur. Chem. Bull., 2019, vol. 8, pp. 63–70. https://doi.org/10.17628/ecb.2019.8.63-70

    Article  CAS  Google Scholar 

  27. Dond, B.D. and Thore, S.N., Tetrahedron Lett., 2020, vol. 61, p. 151660. https://doi.org/10.1016/j.tetlet.2020.151660

    Article  CAS  Google Scholar 

  28. Dond, B.D., Pansare, D.N., Sarkate, A.P., and Thore, S.N., Chem. Paper, 2023, vol. 77, pp. 1765–1772. https://doi.org/10.1007/s11696-022-02585-3

    Article  CAS  Google Scholar 

  29. Gore, V.A., Tekale, S.U., Bhale, S.P., Rajani, D., Domb, A.J., and Pawar, R.P., Lett. App. Nano Biosci., 2021, vol. 10, pp. 1846–1855. https://doi.org/10.33263/LIANBS101.18461855

    Article  Google Scholar 

  30. Karnik, K.S., Sarkate, A.P., Tiwari, S.V., Azad, R., and Wakte, P.S., Bioorg. Chem., 2021, vol. 115, p. 105226. https://doi.org/10.1016/j.bioorg.2021.105226

    Article  CAS  PubMed  Google Scholar 

  31. Tiwari, S.V., Sarkate, A.P., Lokwani, D.K., Pansare, D.N., Gattani, S.G., Sheaikh, S.S., Jain, S.P., and Bhandari, S.V., Bioorg. Med. Chem. Lett., 2022, vol. 67, p. 128747. https://doi.org/10.1016/j.bmcl.2022.128747

    Article  CAS  PubMed  Google Scholar 

  32. Tiwari, S.V., Siddiqui, S., Seijas, J.A., Vazquez-Tato, M.P., Sarkate, A.P., Lokwani, D.K., and Nikalje, A.P.G., Molecules, 2017, vol. 22, p. 995. https://doi.org/10.3390/molecules22060995

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Reddy, V.G., Reddy, T.S., Jadala, C., Reddy, M.S., Sultana, F., Akunuri, R., Bhargava, S.K., Wlodkowic, D., Srihari, P., and Kamal, A., Eur. J. Med. Chem., 2019, vol. 182, p. 111609. https://doi.org/10.1016/j.ejmech.2019.111609

    Article  CAS  PubMed  Google Scholar 

  34. Weigand, M., Hantel, P., Kreienberg, R., and Waltenberger, J., Angiogenesis, 2005, vol. 8, pp. 197–204. https://doi.org/10.1007/s10456-005-9010-0

    Article  CAS  PubMed  Google Scholar 

  35. Aziz, M.A., Serya, R.A.T., Lasheen, D.S., Aziz, A.K.A., Esmat, A., Mansour, A.M, Singab, A.N.B., and Abouzid, K.A.M., Sci. Rep., 2016, vol. 6, p. 24460. https://doi.org/10.1038/srep24460

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Funding

This work was supported by regular institutional funding, and no additional grants were obtained.

Author information

Authors and Affiliations

Authors

Contributions

The authors VAG and DNP selected the literature data on the review topic. The authors APS, SVT, RNS, SVB, and DSB contributed to manuscript preparation.

All authors participated in the discussions.

Corresponding author

Correspondence to D. N. Pansare.

Ethics declarations

This article does not contain any studies involving patients or animals as test objects. Informed consent was not required for this article. No conflict of interest was declared by the authors.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Abbreviations: MCF-7, Human breast cancer cell line; HepG2, Human liver cancer cell line; TLC, Thin layer chromatography.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gore, V.A., Pansare, D.N., Sarkate, A.P. et al. Synthesis, Characterization of Novel Thiazole Hydrazine Derivatives, and Inhibitory Action Against the VEGFR-2. Russ J Bioorg Chem 50, 345–353 (2024). https://doi.org/10.1134/S1068162024020067

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162024020067

Keywords:

Navigation