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Design, synthesis, characterization and catechol oxidase activity of novel class of multi-tripodal pyrazole and triazole-based derivatives

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Abstract

A class of novel multi-tripodal ligands has been prepared via condensation reaction between pyrazole or triazole moieties and N′,N′-bis(2-aminoethyl)ethane-1,2-diamine. Spectroscopic techniques (1H NMR, 13C NMR, IR and mass spectroscopy) have been used to characterize the compounds. The ability of the in situ ligand complexes to catalyze the oxidation reaction of catechol to o-quinone at ambient conditions has been studied. The study demonstrated that the concentration of the metal salt has a pronounced influence on the catalytic activity. Thus, the best result has been obtained with the in situ complex [2 + CuSO4] with an oxidation rate of 21.60 µmol l−1 min−1. Kinetic parameters of the in situ complexes have been also investigated.

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References

  1. J. Kaizer, R. Csonka, G. Speier, M. Giorgi, M. Réglier, J. Mol. Catal. A Chem. 235(1), 81 (2005)

    CAS  Google Scholar 

  2. R. Marion, N.M. Saleh, N. Le Poul, D. Floner, O. Lavastre, F. Geneste, New J. Chem. 36(9), 1828 (2012)

    CAS  Google Scholar 

  3. A. Santra, G. Mondal, M. Acharjya, P. Bera, A. Panja, T.K. Mandal, P. Mitra, P. Bera, Polyhedron 113, 5 (2016)

    CAS  Google Scholar 

  4. R. Marion, M. Zaarour, N.A. Qachachi, N.M. Saleh, F. Justaud, D. Floner, O. Lavastre, F. Geneste, J. Inorg. Biochem. 105(11), 1391 (2011)

    CAS  PubMed  Google Scholar 

  5. S. Choi, S. Kim, H.-J. Lee, H. Lee, Inorg. Chem. Commun. 44, 164 (2014)

    CAS  Google Scholar 

  6. F. Abrigach, R. Touzani, Med. Chem. (Los Angeles) 6(5), 292 (2016)

    Google Scholar 

  7. Y.-H. Luo, G.-G. Wu, S.-L. Mao, B.-W. Sun, Inorg. Chim. Acta 397, 1 (2013)

    CAS  Google Scholar 

  8. F. Malek, N. Draoui, O. Feron, S. Radi, Res. Chem. Intermed. 40(2), 681 (2013)

    Google Scholar 

  9. R. Touzani, A. Ramdani, T. Ben Hadda, S. El Kadiri, O. Maury, H.L. Bozec, P.H. Dixneuf, Synth. Commun. 31(9), 1315 (2001)

    CAS  Google Scholar 

  10. H. Bendaha, L. Yu, R. Touzani, R. Souane, G. Giaever, C. Nislow, C. Boone, S. El Kadiri, G.W. Brown, M. Bellaoui, Eur. J. Med. Chem. 46(9), 4117 (2011)

    CAS  PubMed  Google Scholar 

  11. S. Radi, Y. Toubi, N. Draoui, O. Feron, O. Riant, Lett. Drug Des. Discov. 9(3), 305 (2012)

    CAS  Google Scholar 

  12. S. Radi, Y. Toubi, I. Hamdani, A. Hakkou, F. Souna, I. Himri, M. Bouakka, Res. J. Chem. Sci. 2(4), 40 (2012)

    CAS  Google Scholar 

  13. T. Harit, M. Cherfi, J. Isaad, A. Riahi, F. Malek, Tetrahedron 68(21), 4037 (2012)

    CAS  Google Scholar 

  14. S. Garbacia, C. Hillairet, R. Touzani, O. Lavastre, Collect. Czechoslov. Chem. Commun. 70(1), 34 (2005)

    CAS  Google Scholar 

  15. N. Boussalah, R. Touzani, F. Souna, I. Himri, M. Bouakka, A. Hakkou, S. Ghalem, S.E. Kadiri, J. Saudi Chem. Soc. 17(1), 17 (2013)

    CAS  Google Scholar 

  16. H. Al Bay, B. Quaddouri, A. Guaadaoui, R. Touzani, N.-E. Benchat, A. Hamal, M. Taleb, M. Bellaoui, S. El Kadiri, Lett. Drug Des. Discov. 7(1), 41 (2010)

    CAS  Google Scholar 

  17. A. Zerrouki, K. Karrouchi, F. Abrigach, N. Benchat, M. Taleb, S. El Kadiri, J. Mater. Environ. Sci. 8(1), 90 (2017)

    CAS  Google Scholar 

  18. W.L. Driessen, Recl. Trav. Chim. Pays-Bas 101(12), 441 (1982)

    CAS  Google Scholar 

  19. F. Abrigach, B. Bouchal, O. Riant, Y. Mace, A. Takfaoui, S. Radi, A. Oussaid, M. Bellaoui, R. Touzani, Med. Chem. 12(1), 83 (2016)

    CAS  PubMed  Google Scholar 

  20. M.R. Malachowski, M.G. Davidson, Inorg. Chim. Acta 162(2), 199 (1989)

    CAS  Google Scholar 

  21. S. Kim, D. Kim, H.-J. Lee, H. Lee, J. Mol. Struct. 1063, 70 (2014)

    CAS  Google Scholar 

  22. T. Ben Hadda, A. Kotchevar, M. Daoudi, B. Bennani, N. Larbi, A. Kerbal, Lett. Drug Des. Discov. 2(8), 584 (2005)

    CAS  Google Scholar 

  23. I. Dvoretzky, G.H. Richter, J. Org. Chem. 15(6), 1285 (1950)

    CAS  Google Scholar 

  24. M.S. Pevzner, P.A. Ivanov, N.V. Gladkova, O.N. Sushchenko, V.P. Tverdokhlebov, Z.S. Myasnikova, Chem. Heterocycl. Compd. 16(2), 189 (1980)

    Google Scholar 

  25. R. Boyaala, R. El Ati, F. Abrigach, M. El Kodadi, R. Touzani, B. Hammouti, RJPBCS 8(3), 751 (2017)

    CAS  Google Scholar 

  26. A. Mouadili, F. Abrigach, M. Khoutoul, A. Zarrouk, N. Benchat, R. Touzani, J. Chem. Pharm. Res. 7(1), 968 (2015)

    CAS  Google Scholar 

  27. A. Takfaoui, I. Bouabdallah, F. Abrigach, M. Khoutoul, N. Benchat, R. Touzani, Moroc. J. Chem. 1, 11 (2013)

    Google Scholar 

  28. C. Eicken, B. Krebs, J.C. Sacchettini, Curr. Opin. Struct. Biol. 9(6), 677 (1999)

    CAS  PubMed  Google Scholar 

  29. A. Mouadili, A. Attayibat, S. El Kadiri, S. Radi, R. Touzani, Appl. Catal. A 454, 93 (2013)

    CAS  Google Scholar 

  30. A. Djedouani, F. Abrigach, M. Khoutoul, A. Mohamadou, A. Bendaas, A. Oussaid, R. Touzani, Orient. J. Chem. 31(1), 97 (2015)

    Google Scholar 

  31. U. Boas, J.B. Christensen, P.M.H. Heegaard, J. Mater. Chem. 16(38), 3785 (2006)

    CAS  Google Scholar 

  32. R. Esfand, D.A. Tomalia, Drug Discov. Today 6(8), 427 (2001)

    CAS  PubMed  Google Scholar 

  33. A.-M. Caminade, J.-P. Majoral, Prog. Polym. Sci. 30(3–4), 491 (2005)

    CAS  Google Scholar 

  34. D. Astruc, E. Boisselier, C. Ornelas, Chem. Rev. 110(4), 1857 (2010)

    CAS  PubMed  Google Scholar 

  35. R. Touzani, J. Mater. Environ. Sci. 2(3), 201 (2011)

    Google Scholar 

  36. J.-H. Kim, K. Park, H.Y. Nam, S. Lee, K. Kim, I.C. Kwon, Prog. Polym. Sci. 32(8), 1031 (2007)

    CAS  Google Scholar 

  37. P. Ceroni, G. Bergamini, F. Marchioni, V. Balzani, Prog. Polym. Sci. 30(3–4), 453 (2005)

    CAS  Google Scholar 

  38. R. Duncan, L. Izzo, Adv. Drug Deliv. Rev. 57(15), 2215 (2005)

    CAS  PubMed  Google Scholar 

  39. G.R. Newkome, C.D. Shreiner, Polymer 49(1), 1 (2008)

    CAS  Google Scholar 

  40. D. Staneva, E. Vasileva-Tonkova, M.S.I. Makki, T.R. Sobahi, R.M. Abdel-Rahman, I.H. Boyaci, A.M. Asiri, I. Grabchev, Tetrahedron 71(7), 1080 (2015)

    CAS  Google Scholar 

  41. I. Grabchev, S. Yordanova, E. Vasileva-Tonkova, P. Bosch, S. Stoyanov, Inorg. Chim. Acta 438, 179 (2015)

    CAS  Google Scholar 

  42. I.V. Lijanova, R.G. Monter, N.V. Likhanova, F.V. Garibay, X.O.C. Olivares, Supramol. Chem. 24(1), 56 (2012)

    CAS  Google Scholar 

  43. M.R. Mankbadi, M.A. Barakat, M.H. Ramadan, H.L. Woodcock, J.N. Kuhn, J. Phys. Chem. B 115(46), 13534 (2011)

    CAS  PubMed  Google Scholar 

  44. M.B. Camarada, M. Zúñiga, J. Alzate-Morales, L.S. Santos, Chem. Phys. Lett. 616–617, 171 (2014)

    Google Scholar 

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Authors and Affiliations

  1. Laboratory of Applied Chemistry and Environment, Faculty of Sciences, Mohammed First University, 60000, Oujda, Morocco

    Abdelkhalek Zerrouki, Farid Abrigach & Sghir El Kadiri

  2. Laboratory of Engineering, Electrochemistry, Modeling and Environment, Faculty of Sciences, University Sidi Mohamed Ben Abdellah, Fez, Morocco

    Mustapha Taleb

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  1. Abdelkhalek Zerrouki
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  2. Farid Abrigach
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  3. Mustapha Taleb
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  4. Sghir El Kadiri
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Correspondence to Sghir El Kadiri.

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Zerrouki, A., Abrigach, F., Taleb, M. et al. Design, synthesis, characterization and catechol oxidase activity of novel class of multi-tripodal pyrazole and triazole-based derivatives. Res Chem Intermed 46, 1453–1467 (2020). https://doi.org/10.1007/s11164-019-04044-3

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