Synthesis of novel substituted 3-(4-((1H-benzo[d]imidazol-2-ylthio)methyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-ones: various approaches

Article
  • 10 Downloads

Abstract

Considering benzimidazole as a privileged structure for developing probes of impressive pharmacological potentials, some new coumarin and pyrazole conjugates of benzimidazoles were synthesized with a sulphur linkage. Thus, 3-(2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3) was prepared starting from simple salicylaldehyde which has been used as an important synthon and incorporated in a series of structural manipulations to obtain various of pharmacophoric motif conjugates 9(a–b) and 13(a–f), in fair yields. We have developed facile and stepwise methods for the synthesis of all these compounds in various approaches, which also involves sub-sequences. All synthesized compounds were well characterized by IR, 1HNMR, 13CNMR and mass spectra data.

Graphical Abstract

Keywords

Coumarins Pyrazoles Benzimidazoles Prazoles Various approaches 

Notes

Acknowledgements

The authors are thankful to the authorities of Jawaharlal Nehru Technological University Hyderabad for providing laboratory facilities. They are grateful to Department of Science and Technology, Govt. of India, New Delhi, for financial support to DS in the form of INSPIRE Fellowship.

References

  1. 1.
    D. Srikrishna, G. Chandraiah, P.K. Dubey, Mini-Rev. Med. Chem. 18, 113 (2018)CrossRefGoogle Scholar
  2. 2.
    I.A. Kim, J.H. Shin, I.H. Kim, H.G. Wu, E.K. Chie, S.W. Ha, C.I. Park, G.D. Kao, Clin. Cancer Res. 12, 940 (2006)CrossRefGoogle Scholar
  3. 3.
    W. Tang, H. Hioki, K. Harad, M. Kubo, Y. Fukuyama, J. Nat. Prod. 70, 2010 (2007)CrossRefGoogle Scholar
  4. 4.
    T.H. Stefanova, N.J. Nikolova, R.A. Toshkova, H.O. Neychev, J. Exp. Ther. Oncol. 6, 107 (2007)Google Scholar
  5. 5.
    L. Taneja, A.K. Sharma, R.D. Singh, J. Lumin. 63, 203 (1995)CrossRefGoogle Scholar
  6. 6.
    M. Yamaji, Y. Hakoda, H. Okamoto, F. Tani, Photochem. Photobiol. Sci. 16, 555 (2017)CrossRefGoogle Scholar
  7. 7.
    V. Kumar, K. Kaur, G.K. Gupta, A. Sharma, Eur. J. Med. Chem. 69, 735 (2013)CrossRefGoogle Scholar
  8. 8.
    H.A. Saad, N.A. Osman, A.H. Moustafa, Molecules 16, 10187 (2011)CrossRefGoogle Scholar
  9. 9.
    R. Gondru, J. Banothu, R.K. Thatipamula, S.K.A. Hussain, R. Bavantula, RSC Adv. 5, 33562 (2015)CrossRefGoogle Scholar
  10. 10.
    S. Viveka, P. Dinesha, G.K. Shama, S. Nagaraja, S. Ballav, S. Kerkar, Eur. J. Med. Chem. 101, 442 (2015)CrossRefGoogle Scholar
  11. 11.
    N. Harikrishna, A.M. Isloor, K. Ananda, A. Obaid, H.K. Fun, RSC Adv. 5, 43648 (2015)CrossRefGoogle Scholar
  12. 12.
    S. Dinesha, B. Viveka, K. Priya, K.S.R. Pai, S. Naveen, N.K. Lokanath, G.K. Nagaraja, Eur. J. Med. Chem. 104, 25 (2015)CrossRefGoogle Scholar
  13. 13.
    S. Viveka, P. Dinesha, S. Shama, N.K. Naveen, Lokanath, G.K. Nagaraja, RSC Adv. 5, 94786 (2015)CrossRefGoogle Scholar
  14. 14.
    R. Sridhar, P.T. Perumal, S. Etti, G. Shanmugam, M.N. Ponnuswamy, V.R. Prabavathy, N. Mathivanan, Bio. Org. Med. Chem. Lett. 14, 6035 (2004)CrossRefGoogle Scholar
  15. 15.
    H. Song, Y. Liu, L. Xiong, Y. Li, N. Yang, Q. Wang, J. Agric. Food Chem. 60, 1470 (2012)CrossRefGoogle Scholar
  16. 16.
    H.F. Rizk, M.A. El-Badawi, S.A. Ibrahim, M.A. El-Borai, Arab. J. Chem. 4, 37 (2011)CrossRefGoogle Scholar
  17. 17.
    F. Wang, H. Duan, D. Xing, G. Yang, J. Fluoresc. 27, 1721 (2017)CrossRefGoogle Scholar
  18. 18.
    J.R. Kumar, J.L. Jawahar, D.P. Pathak, Eur. J. Chem. 3, 278 (2006)Google Scholar
  19. 19.
    K.C. Nicolaou, A.J. Roecker, R.V. Summeren, R. Hughes, J.A. Pfefferkorn, N. Winssinger, Bioorg. Med. Chem. 11, 465 (2003)CrossRefGoogle Scholar
  20. 20.
    A.T. Mavrova, D.I. Vuchev, K.K. Anichina, J.A. Tsenov, M.S. Kondeva, M.K. Micheva, Bioorg. Med. Chem. 13, 5550 (2005)CrossRefGoogle Scholar
  21. 21.
    H. Al-Muhaimeed, J. Int. Med. Res. 25, 175 (1997)CrossRefGoogle Scholar
  22. 22.
    S. Demirayak, A.C. Karaburun, U.A. Mohsen, Eur. J. Med. Chem. 37, 255 (2002)CrossRefGoogle Scholar
  23. 23.
    P. Hao, S. Zhang, W.H. Sun, Q. Shi, S. Adewuyi, X. Lu, P. Li, Organometallics 26, 2439 (2007)CrossRefGoogle Scholar
  24. 24.
    D.D. Rajadhyaksha, D.W. Rangnekar, J. Chem. Technol. Biotechnol. 36, 300 (1986)CrossRefGoogle Scholar
  25. 25.
    J.A. Asensio, P. Gomez-Romero, Fuel Cells 5, 336 (2005)CrossRefGoogle Scholar
  26. 26.
    P.C. Tway, L.J.C. Love, J. Phys. Chem. 26, 5223 (1982)CrossRefGoogle Scholar
  27. 27.
    B. Xu, Y. Li, P. Song, F. Ma, M. Sun, Sci Rep. 7, 45688 (2017)CrossRefGoogle Scholar
  28. 28.
    D.S. Strand, D. Kim, D.A. Peura, Gut and Liver 11, 27 (2017)CrossRefGoogle Scholar
  29. 29.
    A. Mejia, W.K. Kraft, Expert Rev. Clin. Pharmacol. 2, 295 (2009)CrossRefGoogle Scholar
  30. 30.
    C. Viegas-Junior, A. Danuello, V. Bolzani, E.J. Barreiro, C.A. Fraga, Curr. Med. Chem. 14, 1829 (2007)CrossRefGoogle Scholar
  31. 31.
    G.L. Liu, Y. Hu, X.H. Chen, G.X. Wang, F. Ling, Bioorg. Med. Chem. Lett. 26, 5039 (2016)CrossRefGoogle Scholar
  32. 32.
    R.K. Arora, N. Kaur, Y. Bansal, G. Bansal, Acta Pharma. Sin. B 4, 368 (2014)CrossRefGoogle Scholar
  33. 33.
    R. Kenchappa, Y.D. Bodke, A. Chandrashekar, M.A. Sindhea, S.K. Peethambar, Arab. J. Chem. 10, S3895 (2017)CrossRefGoogle Scholar
  34. 34.
    R.A.A. Khaled, A.A. Mohamed, H.A.H. Elshemy, N.M. Kahk, D.M. El-Amir, Lett. Drug. Des. Disc. 14, 773 (2017)Google Scholar
  35. 35.
    S.A. Galal, A.S. Abdelsamie, S.A. Shouman, Y.M. Attia, H.I. Ali, A. Tabll, R. El-Shenawy, Y.S. El-Abd, M.M. Ali, A.E. Mahmoud, A.H. Abdel-Halim, A.A. Fyiad, A.S. Girgis, H.I. El-Diwani, Eur. J. Med. Chem. 134, 392 (2017)CrossRefGoogle Scholar
  36. 36.
    B. Mahesh, G. Mohan, S. Santhisudha, Ch. Sridevi, N.V. Reddy, T. Vijaya, C.S. Reddy, Chem. Heterocycl. Compd. 53, 173 (2017)CrossRefGoogle Scholar
  37. 37.
    D. Srikrishna, S. Tasqeeruddin, P.K. Dubey, Lett. Org. Chem. 11, 556 (2014)CrossRefGoogle Scholar
  38. 38.
    D. Srikrishna, P.K. Dubey, Tetrahedron Lett. 55, 6561 (2014)CrossRefGoogle Scholar
  39. 39.
    D. Srikrishna, A. Mallika, P.K. Dubey, Indian J. Chem. 56B, 96 (2017)Google Scholar
  40. 40.
    D. Srikrishna, P.K. Dubey, New J. Chem. 41, 5168 (2017)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryJawaharlal Nehru Technological University Hyderabad College of EngineeringKukatpally, HyderabadIndia

Personalised recommendations