Synthesis, characterization, and molecular docking of benzodiazepines in the presence of SrFe12O19 magnetic nanocatalyst

Abstract

An efficient and concise method for the synthesis of 1,5-benzodiazepine derivatives was developed using o-phenylenediamine derivatives, 4,4-dimethyl cyclohexane-1,3-dione, and different aldehydes through a rapid three-component domino reaction in the presence of the SrFe12O19 magnetic nanocatalyst under solvent-free conditions.The SrFe12O19 nanoparticles were synthesized using the sol–gel auto-combustion technique. The main advantages of using this nanocatalyst are its easy handling and removal from the reaction mixture, by the use of an external magnet, and reusing it several times without any loss of activity. Some parameters such as the bond length and bond strength between the obtained products and the GABA receptor were evaluated to have an insight on the interactions involved. The electrostatic energy, ligand efficiency, log P, and the total binding energy of the compounds with the receptor were also calculated.

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References

  1. 1.

    L. Leggio, G.A. Kenna, R.M. Swift, Prog. Neuropsychopharmacol. Biol. Psychiatry 32, 1106 (2008)

    CAS  PubMed  Article  Google Scholar 

  2. 2.

    K. Bhagat, A. Singh, S. Dhiman, J.V. Singh, R. Kaur, G. Kaur, H.K. Gulati, P. Singh, R. Kumar, R. Salwan, Med. Chem. Res. 28, 2200 (2019)

    CAS  Article  Google Scholar 

  3. 3.

    N. Arora, P. Dhiman, S. Kumar, G. Singh, V. Monga, Bioorg. Chem. 97, 103668 (2020)

    CAS  PubMed  Article  Google Scholar 

  4. 4.

    M.N. Timofeeva, E.A. Petrova, E.A. Mel’gunova, A. Gil, M.A. Vicente, V.N. Panchenko, React. Kinet. Mech. Catal. 127, 41 (2019)

    CAS  Article  Google Scholar 

  5. 5.

    W.-B. Yi, C. Cai, J. Fluorine Chem. 130, 1054 (2009)

    CAS  Article  Google Scholar 

  6. 6.

    M. Kodomari, T. Noguchi, T. Aoyama, Synth. Commun. 34, 1783 (2004)

    CAS  Article  Google Scholar 

  7. 7.

    B.E. Leonard, Hum. Psychopharmacol. Clin. Exp. 14, 125 (1999)

    CAS  Article  Google Scholar 

  8. 8.

    A.M. Holbrook, R. Crowther, A. Lotter, C. Cheng, D. King, Can. Med. Assoc. J. 162, 225 (2000)

    CAS  Google Scholar 

  9. 9.

    J. Xu, G. Zuo, W.L. Chan, Heteroat. Chem. 12, 636 (2001)

    CAS  Article  Google Scholar 

  10. 10.

    H. Uchida, T. Suzuki, D.C. Mamo, B.H. Mulsant, T. Kikuchi, H. Takeuchi, M. Tomita, K. Watanabe, G. Yagi, H. Kashima, J. Anxiety Disord. 23, 477 (2009)

    PubMed  Article  Google Scholar 

  11. 11.

    X.-Q. Pan, J.-P. Zou, Z.-H. Huang, W. Zhang, Tetrahedron Lett. 49, 5302 (2008)

    CAS  Article  Google Scholar 

  12. 12.

    M. Aversa, A. Ferlazzo, P. Giannetto, F. Kohnke, Synthesis. 1986, 230 (1986)

    Article  Google Scholar 

  13. 13.

    A. Chimirri, S. Grasso, R. Ottanà, G. Romeo, M. Zappalà, J. Heterocycl. Chem. 27, 371 (1990)

    CAS  Article  Google Scholar 

  14. 14.

    J.J.V. Eynde, A. Mayence, A. Maquestiau, E. Anders, Bull. Soc. Chim. Belg. 101, 801 (1992)

    Article  Google Scholar 

  15. 15.

    N.N. Kolos, E.N. Yurchenko, V.D. Orlov, S.V. Shishkina, O.V. Shishkin, Chem. Heterocycl. Compd. 40, 1550 (2004)

    CAS  Article  Google Scholar 

  16. 16.

    Y. Wang, M.-S. Tu, F. Shi, S.-J. Tu, Adv. Synth. Catal. 356, 2009 (2014)

    CAS  Article  Google Scholar 

  17. 17.

    X.-T. Zhu, J.-Y. Liu, B. Jiang, S.-J. Tu, J. Heterocycl. Chem. 52, 92 (2015)

    CAS  Article  Google Scholar 

  18. 18.

    J. Dai-Il, C. Tae-wonchoi, K. Yun-Young, K. In-Shik, P. You-Mi, L. Yong-Gyun, J. Doo-Hee, Synth. Commun. 29, 1941 (1999)

    Article  Google Scholar 

  19. 19.

    J.A. Herbert, H. Suschitzky, J. Chem. Soc. Perkin Trans. 1, 2657 (1974)

    Article  Google Scholar 

  20. 20.

    H.R. Morales, A. Bulbarela, R. Contreras, Heterocycles. 24, 135 (1986)

    CAS  Article  Google Scholar 

  21. 21.

    R. Kaoua, B. Nedjar-Kolli, T. Roisnel, Y. Le Gal, D. Lorcy, Tetrahedron. 69, 4636 (2013)

    CAS  Article  Google Scholar 

  22. 22.

    R. Varala, R. Enugala, S. Nuvula, S.R. Adapa, Synlett. 2006, 1009 (2006)

    Article  CAS  Google Scholar 

  23. 23.

    H. Naeimi, H. Foroughi, Chin. J. Catal. 36, 734 (2015)

    CAS  Article  Google Scholar 

  24. 24.

    G. Sabitha, G. Reddy, K.B. Reddy, N.M. Reddy, J. Yadav, Adv. Synth. Catal. 346, 921 (2004)

    CAS  Article  Google Scholar 

  25. 25.

    M.A. Pasha, V.P. Jayashankara, Heterocycles. 68, 1017 (2006)

    CAS  Article  Google Scholar 

  26. 26.

    R.G. Jacob, C.S. Radatz, M.B. Rodrigues, D. Alves, G. Perin, E.J. Lenardao, L. Savegnago, Heteroat. Chem. 22, 180 (2011)

    CAS  Article  Google Scholar 

  27. 27.

    A. Maleki, Tetrahedron. 68, 7827 (2012)

    CAS  Article  Google Scholar 

  28. 28.

    M.R. Shushizadeh, N. Dalband, Jundishapur J. Nat. Pharm. Prod. 7, 61 (2012)

    Google Scholar 

  29. 29.

    H. Naeimi, H. Foroughi, New J. Chem. 39, 1228 (2015)

    CAS  Article  Google Scholar 

  30. 30.

    M. Pozarentzi, J. Stephanidou-Stephanatou, C.A. Tsoleridis, Tetrahedron Lett. 43, 1755 (2002)

    CAS  Article  Google Scholar 

  31. 31.

    M.S. Balakrishna, B. Kaboudin, Tetrahedron Let. 42, 1127 (2001)

    Google Scholar 

  32. 32.

    T. Ahmadi, S. Bahar, G. Mohammadi Ziarani, A. Badiei, Food Chem. 300, 125180 (2019)

    CAS  PubMed  Article  Google Scholar 

  33. 33.

    T. Ahmadi, G. Mohammadi Ziarani, S. Bahar, A. Badiei, J. Iran. Chem. Soc. 15, 1153 (2018)

    CAS  Article  Google Scholar 

  34. 34.

    M.G. Hasab, S.A. Seyyed Ebrahimi, A. Badiei, J. Eur. Ceram. Soc. 27, 3637 (2007)

    Article  CAS  Google Scholar 

  35. 35.

    S. Alamolhoda, S.A. Seyyed Ebrahimi, A. Badiei, J. Magn. Magn. Mater. 303, 69 (2006)

    CAS  Article  Google Scholar 

  36. 36.

    S. Alamolhoda, S.A. Seyyed Ebrahimi, A. Badiei, Iran. Int. J. Sci. 5, 173 (2004)

    CAS  Google Scholar 

  37. 37.

    G. Mohammadi Ziarani, Z. Kazemi Asl, P. Gholamzadeh, A. Badiei, M. Afshar, Appl. Organomet. Chem. 31, e3830 (2017)

    Article  CAS  Google Scholar 

  38. 38.

    G. Mohammadi Ziarani, Z. Kazemi Asl, P. Gholamzadeh, A. Badiei, M. Afshar, J. Sol. Gel Sci. Technol. 85, 103 (2018)

    Article  CAS  Google Scholar 

  39. 39.

    J. Dundas, Z. Ouyang, J. Tseng, A. Binkowski, Y. Turpaz, J. Liang, Nucleic Acids Res. 34, W116 (2006)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  40. 40.

    C.-H. Ngan, D.R. Hall, B. Zerbe, L.E. Grove, D. Kozakov, S. Vajda, Bioinformatics. 28, 286 (2012)

    CAS  PubMed  Article  Google Scholar 

  41. 41.

    M.D.R. Arellano, R. Martínez, E. Cortés, J. Heterocycl. Chem. 19, 321 (1982)

    CAS  Article  Google Scholar 

  42. 42.

    V. Hazai, T. Szabó, B. Volk, M. Milen, Chem. Heterocycl. Compd. 56, 237 (2020)

    CAS  Article  Google Scholar 

  43. 43.

    T.C. Jacob, S.J. Moss, R. Jurd, Nat. Rev. Neurosci. 9, 331 (2008)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  44. 44.

    P.S. Miller, A.R. Aricescu, Nature. 512, 270 (2014)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  45. 45.

    M. Jean, V. Nachbaur, J. Bran, J.-M. Le Breton, J. Alloys Compd. 496, 306 (2010)

    CAS  Article  Google Scholar 

  46. 46.

    Z. Kheilkordi, G. Mohammadi Ziarani, A. Badiei, Polyhedron 178, 114343 (2020)

  47. 47.

    Z. Kheilkordi, G. Mohammadi Ziarani, S. Bahar, A. Badiei, J. Iran. Chem. Soc. 16, 365 (2019)

  48. 48.

    Z. Kheilkordi, G. Mohammadi Ziarani, N. Lashgari, A. Badiei, Polyhedron 166, 203 (2019)

  49. 49.

    Z. KheilKordi, G. Mohammadi Ziarani, A. Badiei, N. Lashgari, Sensor Let. 17, 747 (2019)

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Acknowledgment

We gratefully acknowledge the financial support from the Research Council of Alzahra University and the University of Tehran.

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Correspondence to Ghodsi Mohammadi Ziarani.

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Ahmadi, T., Mohammadi Ziarani, G., Masoumian Hoseini, S. et al. Synthesis, characterization, and molecular docking of benzodiazepines in the presence of SrFe12O19 magnetic nanocatalyst. J IRAN CHEM SOC (2021). https://doi.org/10.1007/s13738-021-02163-6

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Keywords

  • Domino reaction
  • 1,5-Benzodiazepine derivatives
  • Nanomagnethiccatalyst
  • Docking study
  • GABA receptor