Skip to main content
SpringerLink
Log in

One-Pot Multicomponent Synthesis, Molecular Docking, and In Vitro Antibacterial Activities of 1-{(Aryl)[(5-methyl-1,3-thiazol-2-yl)amino]methyl}naphthalen-2-ol

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

Abstract

A series of new Betti bases, 1-{(aryl)[(5-methyl-1,3-thiazol-2-yl)amino]methyl}naphthalen-2-ols, have been synthesized via one-pot three-component reaction of aromatic aldehydes, 5-methyl-1,3-thiazol-2-amine, and naphthalen-2-ol in glycerol in the presence of silica sulfuric acid (SSA) as a catalyst. The synthesized compounds were evaluated for their in vitro antibacterial activity against S. aureus, B. subtilis, E. coli, and P. aeruginosa using ciprofloxacin as a standard drug. Molecular docking analysis ascertained that the anti­microbial potential of these derivatives is determined by inhibition of DNA gyrase. In silico ADMET analysis of the title compounds was also performed.

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

Scheme
Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Chhabria, T.M., Patel, S., Modi, P., and Brahmkshat­riya, S.P., Curr. Top. Med. Chem., 2016, vol. 16, p. 2841. https://doi.org/10.2174/1568026616666160506130731

    Article  CAS  PubMed  Google Scholar 

  2. Powers, L.J., Fogt, S.W., Ariyan, Z.S., Rippin, D.J., Heilman, R.D., and Matthews, R.J., J. Med. Chem., 1981, vol. 24, p. 604. https://doi.org/10.1021/jm00137a022

    Article  CAS  PubMed  Google Scholar 

  3. Sarangi, P.K.N., Sahoo, J., Swain, B.D., Paidesetty, S.K., and Mohanta, G.P., Indian Drugs, 2016, vol. 53, p. 5.

    Article  Google Scholar 

  4. Deb, P.K., Kaur, R., Chandrasekaran, B., Bala, M., Gill, D., and Kaki, V.R., Med. Chem. Res., 2014, vol. 23, p. 2780. https://doi.org/10.1007/s00044-013-0861-4

    Article  CAS  Google Scholar 

  5. Khan, M.-H., Hameed, S., Akhtar, T., Al-Masoudi, N.A., Al-Masoudi, W.A., Jones, P.G., and Pannecouque, C., Med. Chem. Res., 2016, vol. 25, p. 2399. https://doi.org/10.1007/s00044-016-1669-9

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  7. Mishchenko, M., Shtrygol, S., Kaminskyy, D., and Lesyk, R., Sci. Pharm., 2020, vol. 88, article no. 16. https://doi.org/10.3390/scipharm88010016

  8. Sowjanya, C., Seetaram, S.S., Gomathi, S., and Ashok, B.K., Int. J. Adv. Res. Med. Pharm. Sci., 2016, vol. 1, p. 6.

    Google Scholar 

  9. Cardellicchio, C., Capozzi, M.A.M., and Naso, F., Tetra­hedron: Asymmetry, 2010, vol. 21, p. 507. https://doi.org/10.1016/j.tetasy.2010.03.020

    Article  CAS  Google Scholar 

  10. Nishtala, V.B., Mahesh, C., Bhargavi, G., Pasala, V.K., and Basavoju, S., Mol. Diversity, 2020, vol. 24, p. 1139. https://doi.org/10.1007/s11030-019-10017-w

    Article  CAS  Google Scholar 

  11. Shanti, K.D., Shanti, M.D., and Meshram, J.S., J. Comput. Methods Mol. Des., 2016, vol. 6, p. 9.

    Google Scholar 

  12. Pradhan, A., Khan, N., and Goyal, H., Int. J. Theor. Appl. Sci., 2016, vol. 8, p. 41.

    CAS  Google Scholar 

  13. Mohanram, I. and Meshram, J., Med. Chem. Res., 2014, vol. 23, p. 939. https://doi.org/10.1007/s00044-013-0693-2

    Article  CAS  Google Scholar 

  14. Mohanram, I. and Meshram, J., Int. Scholarly Res. Not., 2014, vol. 2014, article ID 639392. https://doi.org/10.1155/2014/639392

  15. Lu, J., Xu, X., Wang, C., He, J., Hu, Y., and Hu, H., Tetrahedron Lett., 2002, vol. 43, p. 8367. https://doi.org/10.1016/S0040-4039(02)01985-8

    Article  CAS  Google Scholar 

  16. Weber, L., Curr. Med. Chem., 2012, vol. 9, p. 2085. https://doi.org/10.2174/0929867023368719

    Article  Google Scholar 

  17. Sunderhaus, J.D. and Martin, S.F., Chem. Eur. J., 2009, vol. 15, p. 1300. https://doi.org/10.1002/chem.200802140

    Article  CAS  PubMed  Google Scholar 

  18. Guan, L., Yang, H., Cai, Y., Sun, L., Di, P., and Li, W., MedChemComm, 2019, vol 10, p. 148. https://doi.org/10.1039/C8MD00472B

  19. Cheng, F., Li, W., Zhou, Y., Shen, J., Wu, Z., and Liu, G., J. Chem. Inf. Model., 2012, vol. 52, p. 3099. https://doi.org/10.1021/ci300367a

    Article  CAS  PubMed  Google Scholar 

  20. Yang, H., Lou, C., Sun, L., Li, J., Cai, Y., Wang, Z., Li, W., Liu, G., and Tang, Y., Bioinformatics, 2019, vol. 35, p. 1067. https://doi.org/10.1093/bioinformatics/bty707

    Article  CAS  PubMed  Google Scholar 

  21. Balouiri, M., Sadiki, M., and Ibnsouda, S.K., J. Pharm. Anal., 2016, vol. 6, p. 71. https://doi.org/10.1016/j.jpha.2015.11.005

    Article  PubMed  Google Scholar 

  22. 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.2019.03.029

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are thankful to the Department of Chemistry, University of Mumbai, Santacruz (East), for spectral analysis and Bharati Vidyapeeth College of Pharmacy, Kolhapur, for molecular docking.

Author information

Authors and Affiliations

  1. Department of Chemistry, Bhavan’s H. Somani College, 400007, Chowpatty, Mumbai, India

    O. A. Lotlikar, S. N. Dandekar & S. V. Rathod

  2. Department of Chemistry, University of Mumbai, 400098, Santacruz (East), Mumbai, India

    M. M. V. Ramana

Authors
  1. O. A. Lotlikar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. N. Dandekar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. M. V. Ramana
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. V. Rathod
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to O. A. Lotlikar or S. V. Rathod.

Ethics declarations

No potential conflict of interest was reported by the authors.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lotlikar, O.A., Dandekar, S.N., Ramana, M.M.V. et al. One-Pot Multicomponent Synthesis, Molecular Docking, and In Vitro Antibacterial Activities of 1-{(Aryl)[(5-methyl-1,3-thiazol-2-yl)amino]methyl}naphthalen-2-ol. Russ J Org Chem 57, 2024–2030 (2021). https://doi.org/10.1134/S1070428021120198

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021120198

Keywords:

Search

Navigation