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Synthesis of New Pyrazole Derivatives, Their Anti-Inflammatory and Analgesic Activities, and Molecular Docking Studies

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Abstract

A new series of coupled benzofuran derivatives that contain the trifluoromethyl group and pyrazole moiety is synthesized for evaluation of their anti-inflammatory and analgesic activities. Their synthesis proceeds via cyclocondensation of 2-hydroxy-4-(trifluoromethyl)benzaldehyde with chloroacetone with formation of 2-acetylbenzofuran, which upon treatment with different aldehydes via the Claisen-Schmidt condensation gives the corresponding chalcones. Cyclization of chalcones with hydrazine hydrate leads to pyrazoline derivatives, that exhibit significant anti-inflammatory and analgesic activities. Docking modelling of selected active compounds are correlated well with their anti-inflammatory tests data.

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References

  1. Farag, A.A., Khalifa, E.M., Sadik, N.A., Abbas, S.Y., Al-Sehemi, A.G., and Ammar, Y.A., Med. Chem. Res., 2013, vol. 22, p. 440. doi https://doi.org/10.1007/s00044-012-0046-6

    Article  CAS  Google Scholar 

  2. Sharma, S., Srivastava, V.K. and Kumar, A., Eur. J. Med. Chem., 2002, vol. 37, p. 689. doi https://doi.org/10.1016/S0223-5234(02)01340-5

    Article  CAS  PubMed  Google Scholar 

  3. Aggarwal, R., Bansal, A., Rozas, I., Kelly, B., Kaushik, P., and Kaushik, D., Eur. J. Med. Chem., 2013, vol. 70, p. 350. doi https://doi.org/10.1016/j.ejmech.2013.09.052

    Article  CAS  PubMed  Google Scholar 

  4. Kumar, R.S., Arif, I.A., Ahamed, A., and Idhayadhulla, A., Saudi J. Biolo. Sci. 2016, vol. 23, p. 614. doi https://doi.org/10.1016/j.sjbs.2015.07.005

    Article  CAS  Google Scholar 

  5. Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y., and Al-aizari, F., Molecules 2018, vol. 23, p. 134. doi https://doi.org/10.3390/molecules23010134

    Article  CAS  PubMed Central  Google Scholar 

  6. Lipman, A.G., Internat. J. Pharm. Pract, 1993, vol. 2, p. 124. doi https://doi.org/10.1111/j.2042-7174.1993.tb00740.x.

    Article  Google Scholar 

  7. Hu, Z.-F., Chen, L.-L., Qi, J., Wang, Y.-H., Zhang, H., and Yu, B.-Y. Fitoterapia, 2011, vol. 82, p. 190. doi https://doi.org/10.1016/j.fitote.2010.09.002.

    Article  CAS  PubMed  Google Scholar 

  8. Diaz, P., Phatak, S.S., Xu, J., Fronczek, F. R., Astruc-Diaz, F., Thompson, C.M., Cavasotto, C.N., and Naguib, M., Chem. Med. Chem.: Chem. Enabl. Drug Discov., 2009, vol. 4, p. 1615. doi https://doi.org/10.1002/cmdc.200900226

    Article  CAS  Google Scholar 

  9. Shakya, A.K., Kamal, M., Balaramnavar, V.M., Bardaweel, S.K., Naik, R.R., Saxena, A.K., and Siddiqui, H., Acta Pharma, 2016, vol. 66, p. 353. doi https://doi.org/10.1515/acph-2016-0023

    Article  CAS  Google Scholar 

  10. Rindhe, S., Rode, M., and Karale, B., Indian J. Pharm. Sci., 2010, vol. 72, p. 231. doi https://doi.org/10.4103/0250-474X.65022

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Ebiike, H., Masubuchi, M., Liu, P., Kawasaki, K.-I., Morikami, K., Sogabe, S., Hayase, M., Fujii, T., Sakata, K., Shindoh, H., Shiratoria, Y., Aoki, Y., Ohtsuka, T., and Shimma, N., Bioorg. Med.C hem. Lett., 2002, vol. 12, p. 607. doi https://doi.org/10.1016/S0960-894X(01)00808-3

    Article  CAS  Google Scholar 

  12. Usachev, B.I., Obydennov, D.L., Röschenthaler, G.-V., and Sosnovskikh, V.Y., Org. Lett., 2008, vol. 10, p. 2857. doi https://doi.org/10.1021/ol800992z

    Article  CAS  PubMed  Google Scholar 

  13. Usachev, B.I., Obydennov, D.L., Röschenthaler, G.-V., and Sosnovskikh, V.Y., J. Fluorine Chem., 2012, vol. 137, p. 22. doi https://doi.org/10.1016/j.jfluchem.2012.01.006

    Article  CAS  Google Scholar 

  14. Ewies, E.F., El-Shehry, M.F., and Boulos, L.S., Int. J. ChemTech. Res., 2014–2015, vol. 7, no. 5, p. 2506

    Google Scholar 

  15. Gouhar, R.S., Ewies, E.F., El-Shehry, M.F., Shaheen, M.N., and Ibrahim, E.M.M., J. Heterocycl. Chem., 2018, vol. 55, p. 2368, doi https://doi.org/10.1002/jhet.3301

    Article  CAS  Google Scholar 

  16. El-Shehry, M.F., Abu-Zied, K.M., Ewies, E.F., Awad, S.M., and Mohram, M.E., Der Pharma Chem., 2013, 5(5), p. 318

    CAS  Google Scholar 

  17. Farag, A.A., El Shehry, M.F., Abbas, S.Y., Abd-Alrahman, S.N., Atrees, A.A., Albasheer, H.Z., and Ammar, Y.A., Z. Naturforsch. B, 2015, vol. 70, p. 519. doi https://doi.org/10.1515/znb-2015-0009

    Article  CAS  Google Scholar 

  18. Wang, Z., Claisen-Schmidt Condensation. Comprehensive Organic Name Reactions and Reagents, Hoboken, NJ: John Wiley & Sons, 2010. doi https://doi.org/10.1002/9780470638859

    Book  Google Scholar 

  19. Nalamachu, S. and Wortmann, R., Postgraduate Med., 2014, vol. 126, p. 92. doi https://doi.org/10.3810/pgm.2014.07.2787

    Article  Google Scholar 

  20. Winter, C.A., Risley, E.A., and Nuss, G.W., Exper.Biol. Med., 1962, vol. 111, p. 544. doi https://doi.org/10.3181/00379727-111-27849

    Article  CAS  Google Scholar 

  21. Matthews, J., Berry, G., and Armitage, P., Statistical Methods in Medical Research, Oxford: Blackwell Science, 2002, 4 ed.

    Google Scholar 

  22. Eddy, N.B. and Leimbach, D., J. Pharma. Exp. Ther., 1953, vol. 107, p. 385. PubMed: 13035677.

    CAS  Google Scholar 

  23. Halgren, T.A., J. Comp. Chem. 1996, vol. 17, p. 490. doi https://doi.org/10.1002/(SICI)1096-987X(199604)17:5/6<490:: AID-JCC1>3.0.CO,2-P

    Article  CAS  Google Scholar 

  24. Morris, G.M., Goodsell, D.S., Halliday, R.S., Huey, R., Hart, W.E., Belew, R.K., and Olson, A.J., J. Comp. Chem., 1998, vol. 19, p. 1639. doi https://doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO,2-B

    Article  CAS  Google Scholar 

  25. Solis, F.J. and Wets, R.J.-B., Math. Oper. Res., 1981, vol. 6, p. 19. doi 0364-765X/81/0601/0019$01.25

    Article  Google Scholar 

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Authors and Affiliations

  1. Pesticide Chemistry Department, National Research Centre, Giza, 12622, Egypt

    M. F. El Shehry

  2. Organometallic and Organometalloid Chemistry Department, National Research Centre, Giza, 12622, Egypt

    E. F. Ewies

  3. Green Chemistry Department, National Research Centre, 33 El-Bohouth St. (former El Tahrir St.), Dokki, Giza, 12622, Egypt

    E. M. Zayed

  4. Al-Zahrawi University College, Karbala, Iraq

    M. F. El Shehry

Authors
  1. M. F. El Shehry
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  2. E. F. Ewies
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  3. E. M. Zayed
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Correspondence to E. F. Ewies.

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El Shehry, M.F., Ewies, E.F. & Zayed, E.M. Synthesis of New Pyrazole Derivatives, Their Anti-Inflammatory and Analgesic Activities, and Molecular Docking Studies. Russ J Gen Chem 89, 492–498 (2019). https://doi.org/10.1134/S1070363219030216

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  • DOI: https://doi.org/10.1134/S1070363219030216

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