Skip to main content
Log in

Synthesis, Antimicrobial Evaluation, and Molecular Docking Study of New Thiazole-5-phenylpropenone Derivatives

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

Abstract

A series of new (E)-1-[2-(2-ethylpyridin-4-yl)-4-methylthiazol-5-yl]-3-phenylprop-2-en-1-one derivatives have been synthesized starting from the antitubercular drug, ethionamide. The synthesized compounds have been tested for their in vitro antimicrobial activity, and five of those have demonstrated promising activity. According to molecular docking study the active compounds have display high binding affinity towards DNA Gyrase and Lumazine Synthase.

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.
Fig. 1.
Fig. 2.

Similar content being viewed by others

REFERENCES

  1. Dan, W. and Dai, J., Eur. J. Med. Chem., 2019, vol. 187, p. 111980. https://doi.org/10.1016/j.ejmech.2019.111980

    Article  CAS  PubMed  Google Scholar 

  2. Singh, P., Anand, A., and Kumar, V., Eur. J. Med. Chem., 2014, vol. 85, p. 758. https://doi.org/10.1016/j.ejmech.2014.08.033

    Article  CAS  PubMed  Google Scholar 

  3. Manjunatha, B., Nagaraja, G.K., Divyaraj, P., Harikrishna, N., Pai, K.S.R., Subhankar, B., and Peethamber, S.K., RSC Adv., 2016, vol. 6, p. 99794. https://doi.org/10.1039/C6RA22705H

    Article  CAS  Google Scholar 

  4. Chu, W.C., Bai, P.Y., Yang, Z.Q., Cui, D.Y., Hua, Y.G., Yang, Y., Yang, Q.Q., Zhang, E., and Qin, S.S., Eur. J. Med. Chem., 2018, vol. 143, p. 905. https://doi.org/10.1016/j.ejmech.2017.12.009

    Article  CAS  PubMed  Google Scholar 

  5. Shelke, S.N., Mhaske, G.R., Bonifácio, V.D.B., and Gawande, M.B., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 5727. https://doi.org/10.1016/j.bmcl.2012.06.072

    Article  CAS  PubMed  Google Scholar 

  6. Sashidhara, K.V., Rao, K.B., Kushwaha, P., Modukuri, R.K., Singh, P., Soni, I., Shukla, P.K., Chopra, S., and Pasupuleti, M., ACS Med. Chem. Lett., 2015, vol. 6, p. 809. https://doi.org/10.1021/acsmedchemLett.5b00169

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Farghaly, T.A., Masaret, G.S., Muhammad, Z.A., and Harrasd, M.F., Bioorg. Chem., 2020, vol. 98, p. 103761. https://doi.org/10.1016/j.bioorg.2020.103761

    Article  CAS  PubMed  Google Scholar 

  8. Coman, F.-M., Mbaveng, A.T., Leonte, D., Bencze, L.C., Vlase, L., Imre, S., Kuete, V., Efferth, T., and Zaharia, V., Med. Chem. Res., 2018, vol. 27, p. 1396. https://doi.org/10.1007/s00044-018-2156-2

    Article  CAS  Google Scholar 

  9. Awoussong, P.K., Zaharia, V., Ngameni, B., Kuete, V., Ntede, H.N., Fokunang, C.N., Abegaz, B.M., and Ngadjui, B.T., Med. Chem. Res., 2015, vol. 24, p. 131. https://doi.org/10.1007/s00044-014-1096-8

    Article  CAS  Google Scholar 

  10. Constantinescu, T., Leonte, D., Bencze, L.C., Vlase, L., Imre, S., Hanganu, D., and Zaharia, V., Farmacia, 2018, vol. 66, p. 663. https://doi.org/10.31925/farmacia.2018.4.16

    Article  CAS  Google Scholar 

  11. Tratrat, C., Haroun, M., Xenikakis, I., Liaras, K., Tsolaki, E., Eleftheriou, P., Petrou, A., Aldhubiab, B., Attimarad, M., Venugopala, K.N., Harsha, S., Elsewedy, H.S., Geronikaki, A., and Soković, M., Curr. Top. Med. Chem., 2019, vol. 19, p. 356. https://doi.org/10.2174/1568026619666190129121933

    Article  CAS  PubMed  Google Scholar 

  12. Liaras, K., Geronikaki, A., Glamocˇlija, J., Círić, A., and Soković, M., Bioorg. Med. Chem., 2011, vol. 19, p. 3135. https://doi.org/10.1016/j.bmc.2011.04.007

    Article  CAS  PubMed  Google Scholar 

  13. Muluk, M.B., Dhumal, S.T., Rehman, N.N.M.A., Dixit, P.P., Kharat, K.R., and Haval, K.P., Chemistry Select, 2019, vol. 4, p. 8993. https://doi.org/10.1002/slct.201902030

    Article  CAS  Google Scholar 

  14. Muluk, M.B., Phatak, P.S., Pawar, S.B., Dhumal, S.T., Rehman, N.N.M.A., Dixit, P.P., Choudhari, P.B., and Haval, K.P., J. Chin. Chem. Soc., 2019, vol. 66, p. 1507. https://doi.org/10.1002/jccs.201900198

    Article  CAS  Google Scholar 

  15. Phatak, P.S., Sathe, B.P., Dhumal, S.T., Rehman, N.N.M.A., Dixit, P.P., Khedkar, V.M., and Haval, K.P., J. Heterocycl. Chem., 2019, vol. 56, p. 1928. https://doi.org/10.1002/jhet.3568

    Article  CAS  Google Scholar 

  16. Thalji, R.K., Raha, K., Andreotti, D., Checchia, A., Cui, H., Meneghelli, G., Profeta, R., Tonelli, F., Tommasi, S., Bakshi, T., Donovan, B.T., Howells, A., Jain, S., Nixon, C., Quinque, G., McCloskey, L., Bax, B.D., Neu, M., Chan, P.F., and Stavenger, R.A., Bioorg. Med. Chem. Lett., 2019, vol. 29, p. 1407. https://doi.org/10.1016/j.bmcl.2019.03

    Article  CAS  PubMed  Google Scholar 

  17. Morgunova, E., Saller, S., Haase, I., Cushman, M., Bacher, A., Fischer, M., and Ladenstein, R., J. Biol. Chem., 2007, vol. 282, p. 17231. https://doi.org/10.1074/jbc.M701724200

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This study was funded by Dr. Babasaheb Ambedkar Marathwada University Aurangabad (grant no. MRP STAT/V1/RG/Dept/2019-20/323-324).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. P. Haval.

Ethics declarations

No conflict of interest was declared by the authors.

Supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patil, P.S., Kasare, S.L., Badar, A.D. et al. Synthesis, Antimicrobial Evaluation, and Molecular Docking Study of New Thiazole-5-phenylpropenone Derivatives. Russ J Gen Chem 90, 1523–1528 (2020). https://doi.org/10.1134/S1070363220080216

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220080216

Keywords:

Navigation