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Characterization and Molecular Docking Study of New 4-Acetamidoalkyl Pyrazoles As B-Raf /Cox-2 Inhibitors

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Abstract

Several new 4-acetamidoalkyl pyrazoles are synthesized by an efficient, one-pot three-component reaction of 3,5-dimethyl-1-phenyl-1H-pyrazole or 3-methyl-1-phenyl-1H-pyrazol-5-ol, aromatic aldehydes, and acetonitrile in the presence of chlorosulfonic acid at room temperature. The products are characterized based on IR, 1H and 13C NMR data and evaluated as potential COX-2 and B-Raf inhibitors by molecular docking studies. All the products showed the potency of B-Raf and COX-2 inhibitory effects with a greater binding affinity to B-Raf than COX-2 protein.

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References

  1. C. Peyssonnaux and A. Eychène. Biol. Cell., 2001, 93, 53–62.

    Article  CAS  PubMed  Google Scholar 

  2. H. Davies, G. R. Bignell, C. Cox, P. Stephens, S. Edkins, S. Clegg, J. Teague, H. Woffendin, M. J. Garnett, and W. Bottomley. Nature, 2002, 417, 949–954.

    Article  CAS  PubMed  Google Scholar 

  3. D. A. Tuveson, B. L. Weber, and M. Herlyn. Cancer Cell, 2003, 4, 95–98.

    Article  CAS  PubMed  Google Scholar 

  4. Y. Cohen, M. Xing, E. Mambo, Z. Guo, G. Wu, B. Trink, U. Beller, W. H. Westra, P. W. Ladenson, and D. Sidransky. J. Natl. Cancer Inst., 2003, 95, 625–627.

    Article  CAS  PubMed  Google Scholar 

  5. X. Xu, R. M. Quiros, P. Gattuso, K. B. Ain, and R. A. Prinz. Cancer Res., 2003, 63, 4561–4567.

    CAS  PubMed  Google Scholar 

  6. K. E. Mercer and C. A. Pritchard. Biochim. Biophys. Acta, 1653, 25–40.

    Google Scholar 

  7. M. J. Garnett and R. Marais. Cancer Cell., 2004, 6, 313–319.

    Article  CAS  PubMed  Google Scholar 

  8. D. Tojo, B. L. Wenig, and K. I. Resnick. Head & Neck, 1995, 17, 137–139.

    Article  CAS  Google Scholar 

  9. J. Ricarte-Filho, I. Ganly, M. Rivera, N. Katabi, W. Fu, A. Shaha, R. M. Tuttle, J. A. Fagin, and R. Ghossein. Thyroid, 2012, 22, 575–584.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. V. Gray-Schopfer, C. Wellbrock, and R. Marais. Nature, 2007, 445, 851–857.

    Article  CAS  PubMed  Google Scholar 

  11. N. Li, D. Batt, and M. Warmuth. Curr. Opin. InVest. Drugs, 2007, 8, 452–456.

    CAS  Google Scholar 

  12. A.-A. Magda, N. I. Abdel-Aziz, A.-M. Alaa, A. S. El-Azab, Y. A. Asiri, and K. E. ElTahir. Bioorg. Med. Chem., 2011, 19, 3416–3424.

    Article  CAS  Google Scholar 

  13. M. El-Sayed, N. I. Abdel-Aziz, A. Abdel-Aziz, A. S. El-Azab, and K. El-Tahir. Bioorg. Med. Chem., 2012, 20, 3306–3316.

    Article  CAS  PubMed  Google Scholar 

  14. B. Balaji, S. Hariharan, D. B. Shah, and M. Ramanathan. Eur. J. Med. Chem., 2014, 86, 469–480.

    Article  CAS  PubMed  Google Scholar 

  15. E. Palaska, G. Sahin, P. Kelicen, N. T. Durlu, and G. Altinok. Il Farmaco, 2002, 57, 101–107.

    Article  CAS  PubMed  Google Scholar 

  16. W. L. Smith and R. Langenbach. J. Clin. Invest., 2001, 107, 1491–1495.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. H. O. Collier. Nature, 1971, 17, 232–234.

    Google Scholar 

  18. M. M. Frank and L.F. Fries. Immunol. Today, 1991, 12, 322–326.

    Article  CAS  PubMed  Google Scholar 

  19. L. Basile, S. Álvarez, A. Blanco, A. Santagati, G. Granata, P. Di Pietro, S. Guccione, and M. Á. Muñoz-Fernández. Eur. J. Med. Chem., 2012, 57, 149–161.

    Article  CAS  PubMed  Google Scholar 

  20. B. Cryer and M. Feldman. Arch. Intern. Med., 1992, 152, 1145–1155.

    Article  CAS  PubMed  Google Scholar 

  21. C. I. Bayly, W. C. Black, S. Léger, N. Ouimet, M. Ouellet, and M. D. Percival. Bioorg. Med. Chem. Lett., 1999, 9, 307–312.

    Article  CAS  PubMed  Google Scholar 

  22. G. Dannhardt, W. Kiefer, G. Krämer, S. Maehrlein, U. Nowe, and B. Fiebich. Eur. J. Med. Chem., 2000, 35, 499–510.

    Article  CAS  PubMed  Google Scholar 

  23. G. Dannhardt and W. Kiefer. Eur. J. Med. Chem., 2001, 36, 109–126.

    Article  CAS  PubMed  Google Scholar 

  24. C. A. Dinarello. Cell., 2010, 140, 935–950.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. N. Ramnath and A. Adjei. Update Cancer Ther., 2007, 2, 111–118.

    Article  Google Scholar 

  26. U. McDermott, S. V. Sharma, L. Dowell, P. Greninger, C. Montagut, J. Lamb, H. Archibald, R. Raudales, A. Tam, and D. Lee. Proc. Natl. Acad. Sci. USA., 2007, 104, 19936–19941.

    Article  PubMed  PubMed Central  Google Scholar 

  27. A. J. King, D. R. Patrick, R. S. Batorsky, M. L. Ho, H. T. Do, S. Y. Zhang, R. Kumar, D. W. Rusnak, A. K. Takle, and D. M. Wilson. Cancer Res., 2006, 66, 11100–11105.

    Article  CAS  PubMed  Google Scholar 

  28. J. A. McCubrey, M. Milella, A. Tafuri, A. M. Martelli, P. Lunghi, A. Bonati, M. Cervello, J. T. Lee, and L. S. Steelman. Curr. Opin. Invest. Drugs, 2008, 9, 614–630.

    CAS  Google Scholar 

  29. G. Bollag, P. Hirth, J. Tsai, J. Zhang, P. N. Ibrahim, H. Cho, W. Spevak, C. Zhang, Y. Zhang, and G. Habets. Nature, 2010, 467, 596–599.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, L. F. Lee, J. W. Malecha, and J. M. Miyashiro. J. Med. Chem., 1997, 40, 1347–1365.

    Article  CAS  PubMed  Google Scholar 

  31. P. Prasit, Z. Wang, C. Brideau, C.-C. Chan, S. Charleson, W. Cromlish, D. Ethier, J. Evans, A. Ford-Hutchinson, and J. Gauthier. Bioorg. Med. Chem. Lett., 1999, 9, 1773–1778.

    Article  CAS  PubMed  Google Scholar 

  32. J. J. Talley, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, W. E. Perkins, R. S. Rogers, A. F. Shaffer, and Y. Y. Zhang. J. Med. Chem., 2000, 43, 775–777.

    Article  CAS  PubMed  Google Scholar 

  33. D. Riendeau, M. Percival, C. Brideau, S. Charleson, D. Dube, D. Ethier, J.-P. Falgueyret, R. Friesen, R. Gordon, G. Greig. J. Pharm. Exp. Ther., 2001, 296, 558–566.

    CAS  Google Scholar 

  34. N. M. Davies and F. Jamali. J. Pharm. Pharm. Sci., 2004, 7, 332–336.

    CAS  PubMed  Google Scholar 

  35. G. Steinbach, P. M. Lynch, R. K. Phillips, M. H. Wallace, E. Hawk, G. B. Gordon, N. Wakabayashi, B. Saunders, Y. Shen, and T. Fujimura. New Eng. J. Med., 2000, 342, 1946–1952.

    Article  CAS  PubMed  Google Scholar 

  36. B. Zhong, X. Cai, S. Chennamaneni, X. Yi, L. Liu, J. J. Pink, A. Dowlati, Y. Xu, A. Zhou, and B. Su. Eur. J. Med. Chem., 2012, 47, 432–444.

    Article  CAS  PubMed  Google Scholar 

  37. C. Blackburn, M. O. Duffey, A. E. Gould, B. Kulkarni, J. X. Liu, S. Menon, M. Nagayoshi, T. J. Vos, and J. Williams. Bioorg. Med. Chem. Lett., 2010, 20, 4795–4799.

    Article  CAS  PubMed  Google Scholar 

  38. X.-L. Ding, H.-Y. Zhang, L. Qi, B.-X. Zhao, S. Lian, H.-S. Lv, and J.-Y. Miao. Bioorg. Med. Chem. Lett., 2009, 19, 5325–5328.

    Article  CAS  PubMed  Google Scholar 

  39. L.-W. Zheng, L.-L. Wu, B.-X. Zhao, W.-L. Dong, and J.-Y. Miao. Bioorg. Med. Chem., 2009, 17, 1957–1962.

    Article  CAS  PubMed  Google Scholar 

  40. S. Bano, K. Javed, S. Ahmad, I. Rathish, S. Singh, and M. Alam. Eur. J. Med. Chem., 2011, 46, 5763–5768.

    Article  CAS  PubMed  Google Scholar 

  41. N. Uramaru, H. Shigematsu, A. Toda, R. Eyanagi, S. Kitamura, and S. Ohta. J. Med. Chem., 2010, 53, 8727–8733.

    Article  CAS  PubMed  Google Scholar 

  42. D. M. Bailey, P. E. Hansen, A. G. Hlavac, E. R. Baizman, J. Pearl, A. F. DeFelice, and M. E. Feigenson. J. Med. Chem., 1985, 28, 256–260.

    Article  CAS  PubMed  Google Scholar 

  43. K. Sujatha, G. Shanthi, N. P. Selvam, S. Manoharan, P. T. Perumal, and M. Rajendran. Bioorg. Med. Chem. Lett., 2009, 19, 4501–4503.

    Article  CAS  PubMed  Google Scholar 

  44. D. Sing. J. Ind. Chem. Soc., 1991, 68, 165–167.

    Google Scholar 

  45. J. J. Liu, M. Y. Zhao, X. Zhang, X. Zhao, and H. L. Zhu. Mini-Rev. Med. Chem., 2013, 13, 1957–1966.

    Article  CAS  PubMed  Google Scholar 

  46. S. Sugiura, S. Ohno, O. Ohtani, K. Izumi, T. Kitamikado, H. Asai, K. Kato, M. Hori, and H. Fujimura. J. Indian Chem. Soc., 1977, 20, 80–85.

    CAS  Google Scholar 

  47. H. Nakagawa, R. Ohyama, A. Kimata, T. Suzuki, and N. Miyata. Bioorg. Med. Chem. Lett., 2006, 16, 5939–5942.

    Article  CAS  PubMed  Google Scholar 

  48. P. Kessler, T. Aybek, G. Neidhart, S. Dogan, V. Lischke, D. H. Bremerich, and C. Byhahn. J. Cardiothorac Vasc. Anesth., 2005, 19, 32–39.

    Article  PubMed  Google Scholar 

  49. A. Davoodnia, M. Bakavoli, A. Vahedinia, M. Rahimizadeh, and M. Roshani. Heterocycles, 2006, 68, 801–806.

    Article  CAS  Google Scholar 

  50. A. Davoodnia, R. Zhiani, M. Roshani, M. Bakavoli, and M. Bashash. Phosphorus, Sulfur, Silicon Relat. Elem., 2007, 182, 1219–1224.

    Article  CAS  Google Scholar 

  51. A. Davoodnia, M. Bakavoli, S. Mohseni, and N. Tavakoli-Hoseini. Monatsh Chem., 2008, 139, 963–965.

    Article  CAS  Google Scholar 

  52. A. Davoodnia, R. Zhiani, and N. Tavakoli-Hoseini. Monatsh Chem., 2008, 139, 1405–1407.

    Article  CAS  Google Scholar 

  53. A. Davoodnia, M. Bakavoli, R. Moloudi, M. Khashi, N. Tavakoli-Hoseini. Chin. Chem. Lett., 2010, 21, 1–4.

    Article  CAS  Google Scholar 

  54. A. Davoodnia, M. Khashi, N. Tavakoli-Hoseini, R. Moloudi, and H. A. Zamani. Monatsh Chem., 2013, 144, 677–680.

    Article  CAS  Google Scholar 

  55. M. Khashi, A. Davoodnia, and J. Chamani. Phosphorus, Sulfur, Silicon Relat. Elem., 2014, 189, 839–848.

    Article  CAS  Google Scholar 

  56. X. Chen, J. She, Z. Shang, J. Wu, H. Wu, and P. Zhang. Synthesis, 2008, 3478–3486.

    Google Scholar 

  57. M. M. Mojtahedi, M. R. Jalali, M. S. Abaee, and M. Bolourtchian. Heterocyc. Commun., 2006, 12, 225–228.

    Article  CAS  Google Scholar 

  58. B. Anxionnat, A. Guérinot, S. Reymond, and J. Cossy. Tetrahedron Lett., 2009, 50, 3470–3473.

    Article  CAS  Google Scholar 

  59. R. G. Kurumbail, A. M. Stevens, J. K. Gierse, J. J. McDonald, R. A. Stegeman, J. Y. Pak, D. Gildehaus, J. M. Miyashiro, T. D. Penning, and K. Seibert. Nature, 1996, 384, 644–648.

    Article  CAS  PubMed  Google Scholar 

  60. B. J. Newhouse, J. D. Hansen, J. Grina, M. Welch, G. Topalov, N. Littman, M. Callejo, M. Martinson, S. Galbraith, and E. R. Laird. Bioorg. Med. Chem. Lett., 2011, 21, 3488–3492.

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    A. Vafaee, A. Davoodnia, M. R. Bozorgmehr & M. Pordel

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  1. A. Vafaee
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  2. A. Davoodnia
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  3. M. R. Bozorgmehr
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  4. M. Pordel
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Correspondence to A. Vafaee.

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Original Russian Text © 2018 A. Vafaee, A. Davoodnia, M. R. Bozorgmehr, M. Pordel.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 59, No. 2, pp. 347–355, March–April, 2018.

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Vafaee, A., Davoodnia, A., Bozorgmehr, M.R. et al. Characterization and Molecular Docking Study of New 4-Acetamidoalkyl Pyrazoles As B-Raf /Cox-2 Inhibitors. J Struct Chem 59, 335–343 (2018). https://doi.org/10.1134/S0022476618020117

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