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Synthesis of Pyrano, Pyrido, Oxazino, and Spiro Pyrazole Derivatives and Their Antimicrobial Activity

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Abstract

Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 4-hydroxybenzaldhyde in alcoholic sodium hydroxide yielded 4-(4-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and treatment of the latter with acetylacetone, hydrazine hydrate, ethyl cyanoacetate, and ethyl acetoacetate gave pyranopyrazole, pyrazolopyrazole, and pyrazolopyridine derivatives. 5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was reacted with 2,4-dichlorobenzoyl isothiocyanate, thiosemicarbazide, and hydrazine hydrate to afford pyrazolooxazine, pyrazolopyrazole, and spiro[pyrazole-3,3′-pyrazolo[3,4-c]pyrazole] derivatives. Some of the newly synthesized compounds showed high antimicrobial activity against three microbial strains (S. aureus, E. coli, C. albicans).

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REFERENCES

  1. Fustero, S., Sánchez-Roselló, M., Barrio, P., and Simón-Fuentes, A., Chem. Rev., 2011, vol. 111, p. 6984. https://doi.org/10.1021/cr2000459

    Article  CAS  PubMed  Google Scholar 

  2. Chao, X. and Ying, O., Dyes Pigm., 2019, vol. 161, p. 303. https://doi.org/10.1016/j.dyepig.2018.09.063

    Article  CAS  Google Scholar 

  3. Parmar, N., Teraiya, S., Patel, R., Barad, H., Jajda, H., and Thakkar, V., J. Saudi Chem. Soc., 2015, vol. 19, p. 36. https://doi.org/10.1016/j.jscs.2011.12.01

    Article  Google Scholar 

  4. Sivakumar, K.K., Rajasekaran, A., Senthilkumar, P., and Wattamwar, P.P., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 2940. https://doi.org/10.1016/j.bmcl.2014.04.067

    Article  CAS  PubMed  Google Scholar 

  5. Ragab, F.A.F., Abdel-Gawad, N.M., Georgey, H.H., and Said, M.F., Chem. Pharm. Bull., 2013, vol. 61, p. 834. https://doi.org/10.1248/cpb.c13-0031

    Article  Google Scholar 

  6. Gouda, M.A., Eldien, H.F., Girges, M.M., and Berghot, M.A., J. Saudi Chem. Soc., 2016, vol. 20, p. 151. https://doi.org/10.1016/j.jscs.2012.06.004

    Article  CAS  Google Scholar 

  7. El Sayed, M.T., El-Sharief, M.A.S., Zarie, E.S., Morsy, N.M., Elsheakh, A.R., Voronkov, A., and Hassan, G.S., Bioorg. Med. Chem. Lett., 2018, vol. 28, p. 952. https://doi.org/10.1016/j.bmcl.2018.01.043

    Article  CAS  PubMed  Google Scholar 

  8. Abdelgawad, M.A., Labib, M.B., Ali, W.A., Kamel, G., Azouz, A.A., and El-Nahass, E.S., Bioorg. Chem., 2018, vol. 78, p. 103. https://doi.org/10.1016/j.bioorg.2018.03.011

    Article  CAS  PubMed  Google Scholar 

  9. Vijesh, A.M., Isloor, A.M., Isloor, S., Shivananda, K.N., Shyma, P.C., and Arulmoli, T., Pharma Chem., 2011, vol. 3, no. 4, p. 454.

    CAS  Google Scholar 

  10. Siyuan, L., Xiaoze, B., and Baomin, W., Chem. Commun., 2018, vol. 54, p. 11515. https://doi.org/10.1039/C8CC06196C

    Article  Google Scholar 

  11. Schmidt, A. and Dreger, A., Curr. Org. Chem., 2011, vol. 15, p. 1423. https://doi.org/10.2174/138527211795378263

    Article  CAS  Google Scholar 

  12. Bao, X., Wei, Sh., Qian, X., Qu, J., Wang, B., Zou, L., and Ge, G., Org. Lett., 2018, vol. 20, p. 3394. https://doi.org/10.1021/acs.orglett.8b01316

    Article  CAS  PubMed  Google Scholar 

  13. Lu, H., Fan, Zh., Xiong, Ch., and Zhang, A., Org. Lett., 2018, vol. 20, p. 3065. https://doi.org/10.1021/acs.orglett.8b01099

    Article  CAS  PubMed  Google Scholar 

  14. Chauhan, P., Mahajan, S., and Enders, D., Chem. Commun., 2015, vol. 51, p. 12890. https://doi.org/10.1039/C5CC04930J

    Article  CAS  Google Scholar 

  15. Petchiappan, A. and Chatterji, D., ACS Omega, 2017, vol. 2, p. 7400. https://doi.org/10.1021/acsomega.7b01368

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Lima, R., del Fiol, F.S., and Balcão, V.M., Front. Pharmacol., 2019, vol. 10, p. 692. https://doi.org/10.3389/fphar.2019.00692

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Cheesman, M.J., Ilanko, A., Blonk, B., and Cock, I.E., Pharmacogn. Rev., 2017, vol. 11, p. 57. https://doi.org/10.4103/phrev.phrev_21_17

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Khan, R., Uddin, M.I., Alam, M.S., Hossain, M.M., and Islam, M.R., Bangladesh J. Pharmacol., 2008, vol. 3, p. 27. https://doi.org/10.3329/bjp.v3i1.834

    Article  Google Scholar 

  19. Dube, P.N., Bule, S.S., Ushir, Y.V., Kumbhare, M.R., and Dighe, P.R., Med. Chem. Res., 2015, vol. 24, p. 1070. https://doi.org/10.1007/s00044-014-1201-z

    Article  CAS  Google Scholar 

  20. Seoane, C., Soto, J.L., Zamorano, P., and Quinteiro, M., J. Heterocycl. Chem., 1981, vol. 18, p. 309. https://doi.org/10.1002/jhet.5570180216

    Article  CAS  Google Scholar 

  21. Atta-ur-Rahman, Choudhary, M.I., and Thomsen, W.J., Bioassay Techniques for Drug Development, London: Harwood Academic, 2001. https://doi.org/10.3109/9780203304532

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Authors and Affiliations

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

    E. F. Abdelrahman, W. Shehta, M. G. M. Assy & M. E. Farhan

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  1. E. F. Abdelrahman
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  2. W. Shehta
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  3. M. G. M. Assy
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  4. M. E. Farhan
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Correspondence to E. F. Abdelrahman.

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Abdelrahman, E.F., Shehta, W., Assy, M.G.M. et al. Synthesis of Pyrano, Pyrido, Oxazino, and Spiro Pyrazole Derivatives and Their Antimicrobial Activity. Russ J Org Chem 56, 1832–1839 (2020). https://doi.org/10.1134/S1070428020100267

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