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Synthesis, Molecular Docking, and In Vitro Antibacterial Activities of Some Novel Aminobenzylnaphthol Derivatives via One-Pot Three-Component Reaction

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Abstract

This work provides the first example of incorporating the thiazole moiety into the aminobenzylnaphthol i.e. Betti base. A series of novel synthesized Betti bases via a one-pot three-component reaction of 2-amino-5-methyl thiazole, 2-naphthol, and substituted aldehydes are reported. The formation of desired products was confirmed using various spectroscopic techniques. The derivatives were screened in vitro for antibacterial activities. Molecular docking was also performed to predict the possible mode of action of these derivatives. The docking analysis ascertained that these derivatives regulate the antimicrobial potential via inhibition of DNA gyrase.

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REFERENCES

  1. Gao, H., Sun, J., and Yan, C.G., Chin. Chem. Lett., 2015, vol. 26, pp. 353–356. https://doi.org/10.1016/j.cclet.2014.11.009

    Article  CAS  Google Scholar 

  2. Olyaei, A. and Sadeghpour, M., RSC Adv., 2019, vol. 9, pp. 18467–1897. https://doi.org/10.1039/c9ra02813g

    Article  CAS  Google Scholar 

  3. Cardellicchio, C., Ciccarella, G., Naso, F., Perna, F., and Tortorella, P., Tetrahedron., 1999, vol. 55, pp. 14685–14692. https://doi.org/10.1016/S0040-4020(99)00914-X

    Article  CAS  Google Scholar 

  4. Georgieva, N.V., Yaneva, Z.L., Simova, S.D., and Nikolova, G.D., Bulg. Chem. Commun., 2017, vol. 49, pp. 201–208.

    Google Scholar 

  5. Chopde, H.N., Meshram, J.S., Pagadala, R., and Mungole, A.J., Int. J. ChemTech Res., 2010, vol. 2, pp. 1823–1830.

    CAS  Google Scholar 

  6. Adrián, P., Alexis, R.G., Roderick, A., Kaylie, D., Miguel, X.F., and Giovanna, B., J. Mol. Clin. Med., 2019, vol. 2, p. 35. https://doi.org/10.31083/j.jmcm.2019.02.7181

    Article  Google Scholar 

  7. Shen, A.Y., Tsai, C.T., and Chen, C.L., Eur. J. Med. Chem., 1999, vol. 34, pp. 877–882. https://doi.org/10.1016/S0223-5234(99)00204-4

    Article  CAS  Google Scholar 

  8. Mohanram, I. and Meshram, J., ISRN Org. Chem., 2014, vol. 2014, pp. 1–7. https://doi.org/10.1155/2014/639392

    Article  Google Scholar 

  9. Cimarelli, C., Molecules, 2019, vol. 24, pp. 4–5. https://doi.org/10.3390/molecules24132372

    Article  CAS  Google Scholar 

  10. Cardellicchio, C., Capozzi, M.A.M., and Naso, F., Tetrahedron Asymmetry, 2010, vol. 21, pp. 507–517. https://doi.org/10.1016/j.tetasy.2010.03.020

    Article  CAS  Google Scholar 

  11. Olyaei, A., Abforushha, E.S., and Khoeiniha, R., Lett. Org. Chem., 2017, vol. 14, pp. 103–108. https://doi.org/10.2174/15701786146661702011714

    Article  CAS  Google Scholar 

  12. Guan, L., Yang, H., Cai, Y., Sun, L., Di, P., and Li, W., Med. Chem. Commum., 2019, vol. 10, pp. 148–157. https://doi.org/10.1039/C8MD00472B

    Article  CAS  Google Scholar 

  13. Cheng, F., Li, W., Zhou, Y., Shen, J., Wu, Z., Liu, G., J. Chem. Inf. Model., 2012, vol. 52, pp. 3099–3105. https://doi.org/10.1021/ci300367a

    Article  CAS  PubMed  Google Scholar 

  14. Yang, H., Lou, C., Sun, L., Li, J., Cai, Y., Wang, Z. Bioinformatics, 2019, vol. 35, pp. 1067–1069. https://doi.org/10.1093/bioinformatics/bty707

    Article  CAS  PubMed  Google Scholar 

  15. Balouiri, M., Sadiki, M., and Ibnsouda, S.K., J. Pharm. Anal., 2016, vol. 6, pp. 71–79. https://doi.org/10.1016/j.jpha.2015.11.005

    Article  PubMed  Google Scholar 

  16. Chen, P., Lee, N.V., Hu, W., Xu, M., Ferre, R.A., and Lam, H., Mol. Cancer Ther., 2016, vol. 15, pp. 2273–2281. https://doi.org/10.1158/1535-7163.MCT-16-0300

    Article  CAS  PubMed  Google Scholar 

  17. Thalji, R.K., Raha, K., Andreotti, D., Checchia, A., Cui, H., Meneghelli, G. Bioorg. Med. Chem. Lett., 2019, vol. 29, pp. 1407–1412. https://doi.org/10.1016/j.bmcl.2019.03.029

    Article  CAS  PubMed  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to the Department of Chemistry, University of Mumbai, Santacruz (E.) for spectral analysis, Bharati Vidyapeeth College of Pharmacy, Kolhapur for computational studies.

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Correspondence to Shrimant V. Rathod.

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The online version contains supplementary material available at https://doi.org/10.1134/S1068162021040075.

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Dandekar, S.N., Lotlikar, O.A., Ramana, M.M. et al. Synthesis, Molecular Docking, and In Vitro Antibacterial Activities of Some Novel Aminobenzylnaphthol Derivatives via One-Pot Three-Component Reaction. Russ J Bioorg Chem 47, 874–881 (2021). https://doi.org/10.1134/S1068162021040075

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