Synthesis of new pyrazolone-based heterocycles as inhibitors of monoamine oxidase enzymes

  • Taha M. A. Eldebss
  • Xue-Jing Yi
  • Ahmad M. Farag
  • Ahmad A. Khedr
  • Mohamed M. Abdulla
  • Yahia N. Mabkhot
Original Paper
  • 18 Downloads

Abstract

A series of new substituted pyrazoles embedded with a variety of function groups has been synthesized from 4-[4-(1,2-dihydro-2,3-dimethyl-1-phenyl-5-oxo-3H-pyrazol-4-yl)]-2-cyano-4-oxo-butanenitrile (4). The synthesized compounds were fully characterized and their structures were elucidated based on elemental analysis, spectral data, and alternative synthetic pathways, whenever possible. The pharmacological activities of these new compounds as inhibitors for of type A and type B monoamine oxidase (MAO) enzymes have been investigated and compared to the most common inhibitors of MAO enzymes used to treat depression and anxiety such as deprenyl (selegiline), moclobemide, and clorgyline drugs. The most potent of the synthesized compounds was 4, 11, and 53 which showed higher inhibition activity toward type A MAO enzyme and even exceeded that of deprenyl, moclobemide, and clorgyline drugs.

Keywords

Monoamine oxidase (MAO) enzyme Pyrazoles Type A and type B monoamine oxidase inhibitors IC50 Deprenyl 

Notes

Acknowledgements

The authors would like to extend their sincere appreciation to the Deanship of the Scientific Research at King Saud University for the support of the Research (PRG-1437-29).

References

  1. 1.
    D.P. Holschneider, J.C. Shih, Monoamine oxidase: basic and clinical perspectives. Psychopharmacol Fourth Gener Progress. http://www.acnp.org/g4/GN401000046/CH046.html
  2. 2.
    A. Kleemann, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances (Thieme, New York, 1999)Google Scholar
  3. 3.
    A.M. Sh. El-Sharief, M.A. Zahran, M.S.A. Elgaby, Y.A. Ammar, U.H. Elsaid, Afinidad 60, 81–87 (2003)Google Scholar
  4. 4.
    J.N. Domínguez, J.E. Charris, M. Caparelli, F. Riggione, Arzeimittelforschung 52, 482–488 (2002)Google Scholar
  5. 5.
    A. Giraldez, R. Nieves, C. Ochoa, C. Vara de Rey, E. Cenarruzabeitia, B. Lasheras, Eur. J. Med. Chem. 24, 497–502 (1989)CrossRefGoogle Scholar
  6. 6.
    A.M. Gonzalez, M.G. Chamorro, Farm. Clin. 6, 426–440 (1989)Google Scholar
  7. 7.
    D.W.K. Acheson, S. Uden, J.M. Braganaza, S.W. Brown, J.B. Houston, Br. J. Clin. Pharmac. 24, 812–815 (1987)CrossRefGoogle Scholar
  8. 8.
    S.I. Abakarov, N.I. Benzonova, S. Kh Kalamkarova. V.P. Kirakosyan, USSR SU, 1442214 (1988) [Chem. Abstr. 111, 160304r (1889)] Google Scholar
  9. 9.
    W.R. Berry, G. Kirshenbaum, C. Hoilien, M. Le, J. Reichen, Gastroentrology 88, 397–402 (1985)CrossRefGoogle Scholar
  10. 10.
    J.V. St. W.M. Peter, Awni, Clin. Pharmackinet. 20, 50–65 (1991)CrossRefGoogle Scholar
  11. 11.
    C.K. Svensson, R.K. Dorbitch, K.A. Kloss, J. Pharm. Sci. 80, 225–228 (1991)CrossRefGoogle Scholar
  12. 12.
    J.E. Baggott, S.L. Morgan, T. Ha, W. Vaughn, R.J. Hine, Biochem. J. 282, 197–202 (1992)CrossRefGoogle Scholar
  13. 13.
    D. Schillaci, B. Maggio, D. Raffa, G. Daidone, Farmacology 47, 127–129 (1992)Google Scholar
  14. 14.
    G.W. Mihaly, S.A. Ward, D.D. Nicholl, G. Edwards, A.M. Breckenridge, Biochem. Phamacol. 34, 331–336 (1985)CrossRefGoogle Scholar
  15. 15.
    A.M. Farag, K.A.K. Ali, T.M.A. El-Debss, A.S. Mayhoub, A.E. Amr, N.A. Abdel-Hafez, M.M. Abdulla, Eur. J. Med. Chem. 45, 5887–5898 (2010)CrossRefGoogle Scholar
  16. 16.
    A.M. Farag, A.S. Mayhoub, T.M.A. Eldebss, A.E. Amr, K.A.K. Ali, N.A. Abdel-Hafez, M.M. Abdulla, Arch. Pharm. Chem. Life Sci. 343, 384–396 (2010)CrossRefGoogle Scholar
  17. 17.
    X.-J. Yi, T.T. El-Idreesy, T.M.A. Eldebss, A.M. Farag, M.M. Abdulla, S.A. Hassan, Y.N. Mabkhot, Chem. Biol. Drug Des. 88, 832–843 (2016)CrossRefGoogle Scholar
  18. 18.
    D. Secci, A. Bolasco, P. Chimenti, S. Carradori, Curr. Med. Chem. 18, 5114–5144 (2011)CrossRefGoogle Scholar
  19. 19.
    F. Chimenti, A. Bolasco, F. Manna, D. Secci, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, F. Ortuso, Chem. Biol. Drug Des 67, 206–214 (2006)CrossRefGoogle Scholar
  20. 20.
    D. Secci, S. Carradori, A. Bolasco, B. Bizzarri, M. D’Ascenzio, E. Maccioni, Curr. Top. Med. Chem. 12, 2240–2257 (2012)CrossRefGoogle Scholar
  21. 21.
    J. Zhu, H. Bienaime, Multicomponent Reactions (Wiley, Weinheim, 2005)CrossRefGoogle Scholar
  22. 22.
    L.F. Tietze, G. Brasche, K.M. Gericke, Domino Reactions in Organic Synthesis (Wiley, Weinheim, 2006)CrossRefGoogle Scholar
  23. 23.
    R.V.A. Orru, M. de Greef, Synthesis 10, 1471 (2003)CrossRefGoogle Scholar
  24. 24.
    D.J. Ramon, M. Yus, Angew. Chem. Int. Edit. 44, 1602 (2005)CrossRefGoogle Scholar
  25. 25.
    G. Guillena, D.J. Ramon, M. Yus, Organocatal Tetrahedron Asymmetry 18, 693 (2007)CrossRefGoogle Scholar
  26. 26.
    A. Padwa, S.K. Bur, M. Yus, Tetrahedron 63, 5341 (2007)CrossRefGoogle Scholar
  27. 27.
    D.J. Vugts, M.M. Koningstein, R.F. Schmitz, F.J.J. de Kanter, M.B. Groen, R.V.A. Orru, Chem. Eur. J. 12, 7178 (2006)CrossRefGoogle Scholar
  28. 28.
    T.E. Nielsen, S.L. Schreiber, Angew. Chem. Int. Edit. 47, 48 (2008)CrossRefGoogle Scholar
  29. 29.
    M. Azizmohammadi, M. Khoobi, A. Ramazani, S. Emami, A. Shafiee, Eur. J. Med. Chem. 59, 15–22 (2013)CrossRefGoogle Scholar
  30. 30.
    Z.Z. Mehdi, K.A. Ramazania, A. Foroumadib, A.S. Katarzyna, ŚT. Lisd, A. Shafieee Tetrahedron 68, 6721–6726 (2012)CrossRefGoogle Scholar
  31. 31.
    M. Rouhania, A. Ramazania, S. WooJoob, Ultrason. Sonochem. 22, 391–396 (2015)CrossRefGoogle Scholar
  32. 32.
    R. Ali, R.K. Ali Curr. Organ. Chem. 15, 3986–4020 (2011)CrossRefGoogle Scholar
  33. 33.
    A.R. Mehdi, K.A. Torkamana, F.Z. Nasrabadic, H.F. Mojtaba, S.M. Jafarid, A.A. Saeed, E. Mohammad, A.F. Alireza, A. Foroumadib, A. Shafieeb Eur. J. Med. Chem. 78, 151–156 (2014)CrossRefGoogle Scholar
  34. 34.
    R.K. Ali, R. Ali Curr. Org. Chem. 16, 418–450 (2012)CrossRefGoogle Scholar
  35. 35.
    A. Ramazani, P.A. Asiabi, H. Aghahosseini, F. Gouranlou, Curr. Org. Chem. 21, 908–922 (2017)CrossRefGoogle Scholar
  36. 36.
    H. Aghahosseini, A. Ramazani, F. Gouranlou, S.W. Joo, Curr. Org. Synth. 14, 810–864 (2017)Google Scholar
  37. 37.
    S.T. Fardood, A. Ramazani, S. Moradi, J. Sol Gel Sci. Technol. 82, 432–439 (2017)CrossRefGoogle Scholar
  38. 38.
    M. Rouhania, A. Ramazani, S.W. Joo Ultrason. Sonochem. 21, 262–267 (2014)CrossRefGoogle Scholar
  39. 39.
    E. Dario, M. Bossani, J.-M. Lehn, Bull. Soc. Chim. Fr 26, 1665 (1989)Google Scholar
  40. 40.
    K. Matsumoto, I. Uno, K. Kato, T. Ishikawa, Yeast 1, 25–38 (1985)CrossRefGoogle Scholar
  41. 41.
    R.E. Basford, Preparation and properties of brain mitochondria. Methods Enzymol 10, 96–101 (1967)CrossRefGoogle Scholar
  42. 42.
    H. Fankhauser, M.E. Schweingruber, Gene 147, 141–144 (1994)CrossRefGoogle Scholar
  43. 43.
    D.G. Graham-Smith, Br. J. Pharmacol. 43, 856–864 (1971)CrossRefGoogle Scholar
  44. 44.
    S. Weggen, J.L. Eriksen, S.A. Sagi, C.U. Pietrzik, T.E. Golde, E.H. Koo, J. Biol. Chem. 278, 30748–30754 (2003)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceCairo UniversityGizaEgypt
  2. 2.Yueyang Vocational Technical CollegeYueyangChina
  3. 3.Research UnitSaco Pharm. Co.6th October CityEgypt
  4. 4.Department of Chemistry, College of ScienceKing Saud UniversityRiyadhSaudi Arabia

Personalised recommendations