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Novel Triazole-, Oxadiazole-, and Pyrazole-Nicotinonitrile Hybrids: Synthesis, DFT Study, Molecular Docking, and Antimicrobial Activity

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Abstract

The present study is devoted to functionalization of ethyl 2-{[3-cyano-6-(4-cyanophenyl)-4-(2,4-dichlorophenyl)pyridin-2-yl]oxy}acetate (1) by triazole-, oxadiazole- and pyrazole-nicotinonitrile hybrids, and study of their DFT and antimicrobial properties. Nicotinonitrile can be alkylated by ethyl bromoacetate, its following hydrazonolysis with hydrazine hydrate leads to the corresponding acetic acid derivative. The latter compound has been functionalized to 1,3,4-oxadiazoles by the reaction with carboxylic acid derivatives in presence of phosphorus oxychloride. 1,2,4-Triazoles and pyrazoles have been obtained by heterocyclization of pyridine 1 with phenyl/cyclohexyl isothiocyanate, acetyl acetone, ethyl acetoacetate, and ethyl cycanoacetate. Several products demonstrate moderate activity against some bacteria and fungi.

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REFERENCES

  1. Amr, A.E. and Mohamed, M.A., Bioorg. Med. Chem., 2006, vol. 14, p. 4341. https://doi.org/10.1016/j.bmc.2006.02.045

    Article  CAS  PubMed  Google Scholar 

  2. Maria, T.C., Cenzo, C., and Valentina, O., Eur. J. Med. Chem., 2000, vol. 35, p. 545. https://doi.org/10.1016/S0223-5234(00)00149-5

    Article  Google Scholar 

  3. Igor, V.M., Madhuri, M., Nikolai, M.E., Eerik, M.E., Elena, R., Marcia, A.O., Jennifer, D.B., Nikolai, M.P., Snezna, R., and Alexander, K., Med. Chem. Lett., 2007, vol. 17, p. 3872. https://doi.org/10.1016/j.bmcl.2007.05.004

  4. Wenmin, C., Peng, Z., Diwakar, R., Erik, D.C., Christophe, P., Jan, B., Zhongxia, Z., Huiqing, L., and Xinyong, L., Bioorg. Med. Chem. 2014, vol. 22, p. 1863. https://doi.org/10.1016/j.bmc.2014.01.054

  5. El-Sayed, H.A., Moustafa, A.H., El-Torky, A.E., and Abd El-Salam, E.A., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2401. https://doi.org/10.1134/S107036321710022X

    Article  CAS  Google Scholar 

  6. El-Sayed, H.A. and Morsy, H.A., J. Iran. Chem. Soc., 2019, vol. 16, p. 723. https://doi.org/10.1007/s13738-018-1548-z

  7. Abdel Hamid, A.M., El-Sayed, H.A., Mohammed, S.M., Moustafa A.H., and Morsy, H.A., Russ. J. Gen. Chem., 2020, vol. 90, no. 3, p. 476. https://doi.org/10.1134/S1070363220030226

  8. El-Sayed, H.A., Abdel Hamid, A.M., Mohammed S.M., and Moustafa, A.H., Synth. Commun. 2019, vol. 49, no. 16, p. 2096. https://doi.org/10.1080/00397911.2019.1616760

  9. El-Sayed, H.A., Moustafa, A.H., and Abd El-Salam, E.A., J Heterocyclic Chem. 2020, vol. 57. p. 2738. https://doi.org/10.1002/jhet.3982

  10. Dog, W.-L., Xu, J.-Y., Xiong, L.-X., and Li, Z.-M., J. Iran. Chem. Soc. 2013, vol. 10, p. 429.

  11. Doherty, G.O.P., U.S. Patent 3 962 263; Chem. Abstr., 1976, vol. 85, 159901w.

  12. Rateb, N.M., J. Heterocycl. Chem., 2014, vol. 51, p. 1349. https://doi.org/10.1002/jhet.1799

    Article  CAS  Google Scholar 

  13. Singha, P., Quraishia, M.A., Guptab, S.L., Dandiab, A., and Taibah, J., Univ. Sci. 2016, vol. 10, p. 139. https://doi.org/10.1016/j.jtusci.2015.07.005

  14. Gondek, E., Kityk, I.V., Danel, A., Wisla, A., Pokladko, M., Sanetra, J., and Sahraoui, B., Mater. Lett., 2006, vol. 60, p. 3301. https://doi.org/10.1016/j.matlet.2006.03.051

  15. Calus, S., Gondek, E., Danel, A., Jarosz, B., Niziol, J., and Kityk, A.V., Mater. Sci. Eng. B Solid, 2007, vol. 137, p. 255. https://doi.org/10.1016/j.mseb.2006.11.028

  16. El-Sayed, H.A., Moustafa, A.H., Said, S.A., Assy, M.G., and Amr, A.E., Synth. Commun., 2018, vol. 48, no. 20, p. 2615. https://doi.org/10.1080/00397911.2018.1496262

    Article  CAS  Google Scholar 

  17. El-Sayed, H.A. and Said, S.A., J. Heterocyclic Chem., 2019, vol. 56, p. 1030. https://doi.org/10.1002/jhet.3488

  18. El-Sayed, H.A., Moustafa, A.H., Haikal, A.Z., Abu-El-Halawa, R., and El Ashry, E.S.H., Eur. J. Med. Chem. 2011, vol. 46, p. 2948. https://doi.org/10.1016/j.ejmech.2011.04.019

  19. El-Sayed, H.A., J. Iran. Chem. Soc., 2017, vol. 14, p. 2239. https://doi.org/10.1007/s13738-017-1160-7

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Zagazig University, 44519, Zagazig, Egypt

    Hassan A. El-Sayed, Ahmed H. Moustafa, Ahmed F. El Farargy, Samar M. Mohammed & Esraa Saudy

  2. Department of Chemistry, Faculty of Science, Suez Canal Univeristy, 41522, Ismailia, Egypt

    Emad M. Gad

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  1. Hassan A. El-Sayed
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  2. Ahmed H. Moustafa
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  3. Ahmed F. El Farargy
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  4. Samar M. Mohammed
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Correspondence to Hassan A. El-Sayed or Ahmed H. Moustafa.

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El-Sayed, H.A., Moustafa, A.H., Farargy, A.F.E. et al. Novel Triazole-, Oxadiazole-, and Pyrazole-Nicotinonitrile Hybrids: Synthesis, DFT Study, Molecular Docking, and Antimicrobial Activity. Russ J Gen Chem 92, 709–717 (2022). https://doi.org/10.1134/S1070363222040120

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