Skip to main content
SpringerLink
Log in

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

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

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

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9

Similar content being viewed by others

References

  1. D. Srikrishna, G. Chandraiah, P.K. Dubey, Mini-Rev. Med. Chem. 18, 113 (2018)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  3. W. Tang, H. Hioki, K. Harad, M. Kubo, Y. Fukuyama, J. Nat. Prod. 70, 2010 (2007)

    Article  CAS  PubMed  Google Scholar 

  4. T.H. Stefanova, N.J. Nikolova, R.A. Toshkova, H.O. Neychev, J. Exp. Ther. Oncol. 6, 107 (2007)

    CAS  PubMed  Google Scholar 

  5. L. Taneja, A.K. Sharma, R.D. Singh, J. Lumin. 63, 203 (1995)

    Article  CAS  Google Scholar 

  6. M. Yamaji, Y. Hakoda, H. Okamoto, F. Tani, Photochem. Photobiol. Sci. 16, 555 (2017)

    Article  CAS  PubMed  Google Scholar 

  7. V. Kumar, K. Kaur, G.K. Gupta, A. Sharma, Eur. J. Med. Chem. 69, 735 (2013)

    Article  CAS  PubMed  Google Scholar 

  8. H.A. Saad, N.A. Osman, A.H. Moustafa, Molecules 16, 10187 (2011)

    Article  CAS  PubMed  Google Scholar 

  9. R. Gondru, J. Banothu, R.K. Thatipamula, S.K.A. Hussain, R. Bavantula, RSC Adv. 5, 33562 (2015)

    Article  CAS  Google Scholar 

  10. S. Viveka, P. Dinesha, G.K. Shama, S. Nagaraja, S. Ballav, S. Kerkar, Eur. J. Med. Chem. 101, 442 (2015)

    Article  CAS  PubMed  Google Scholar 

  11. N. Harikrishna, A.M. Isloor, K. Ananda, A. Obaid, H.K. Fun, RSC Adv. 5, 43648 (2015)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  13. S. Viveka, P. Dinesha, S. Shama, N.K. Naveen, Lokanath, G.K. Nagaraja, RSC Adv. 5, 94786 (2015)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  15. H. Song, Y. Liu, L. Xiong, Y. Li, N. Yang, Q. Wang, J. Agric. Food Chem. 60, 1470 (2012)

    Article  CAS  PubMed  Google Scholar 

  16. H.F. Rizk, M.A. El-Badawi, S.A. Ibrahim, M.A. El-Borai, Arab. J. Chem. 4, 37 (2011)

    Article  CAS  Google Scholar 

  17. F. Wang, H. Duan, D. Xing, G. Yang, J. Fluoresc. 27, 1721 (2017)

    Article  CAS  PubMed  Google Scholar 

  18. J.R. Kumar, J.L. Jawahar, D.P. Pathak, Eur. J. Chem. 3, 278 (2006)

    CAS  Google Scholar 

  19. K.C. Nicolaou, A.J. Roecker, R.V. Summeren, R. Hughes, J.A. Pfefferkorn, N. Winssinger, Bioorg. Med. Chem. 11, 465 (2003)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  21. H. Al-Muhaimeed, J. Int. Med. Res. 25, 175 (1997)

    Article  CAS  PubMed  Google Scholar 

  22. S. Demirayak, A.C. Karaburun, U.A. Mohsen, Eur. J. Med. Chem. 37, 255 (2002)

    Article  CAS  PubMed  Google Scholar 

  23. P. Hao, S. Zhang, W.H. Sun, Q. Shi, S. Adewuyi, X. Lu, P. Li, Organometallics 26, 2439 (2007)

    Article  CAS  Google Scholar 

  24. D.D. Rajadhyaksha, D.W. Rangnekar, J. Chem. Technol. Biotechnol. 36, 300 (1986)

    Article  CAS  Google Scholar 

  25. J.A. Asensio, P. Gomez-Romero, Fuel Cells 5, 336 (2005)

    Article  CAS  Google Scholar 

  26. P.C. Tway, L.J.C. Love, J. Phys. Chem. 26, 5223 (1982)

    Article  Google Scholar 

  27. B. Xu, Y. Li, P. Song, F. Ma, M. Sun, Sci Rep. 7, 45688 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. D.S. Strand, D. Kim, D.A. Peura, Gut and Liver 11, 27 (2017)

    Article  PubMed  Google Scholar 

  29. A. Mejia, W.K. Kraft, Expert Rev. Clin. Pharmacol. 2, 295 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. C. Viegas-Junior, A. Danuello, V. Bolzani, E.J. Barreiro, C.A. Fraga, Curr. Med. Chem. 14, 1829 (2007)

    Article  CAS  PubMed  Google Scholar 

  31. G.L. Liu, Y. Hu, X.H. Chen, G.X. Wang, F. Ling, Bioorg. Med. Chem. Lett. 26, 5039 (2016)

    Article  CAS  PubMed  Google Scholar 

  32. R.K. Arora, N. Kaur, Y. Bansal, G. Bansal, Acta Pharma. Sin. B 4, 368 (2014)

    Article  Google Scholar 

  33. R. Kenchappa, Y.D. Bodke, A. Chandrashekar, M.A. Sindhea, S.K. Peethambar, Arab. J. Chem. 10, S3895 (2017)

    Article  CAS  Google Scholar 

  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. 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)

    Article  CAS  PubMed  Google Scholar 

  36. B. Mahesh, G. Mohan, S. Santhisudha, Ch. Sridevi, N.V. Reddy, T. Vijaya, C.S. Reddy, Chem. Heterocycl. Compd. 53, 173 (2017)

    Article  CAS  Google Scholar 

  37. D. Srikrishna, S. Tasqeeruddin, P.K. Dubey, Lett. Org. Chem. 11, 556 (2014)

    Article  CAS  Google Scholar 

  38. D. Srikrishna, P.K. Dubey, Tetrahedron Lett. 55, 6561 (2014)

    Article  CAS  Google Scholar 

  39. D. Srikrishna, A. Mallika, P.K. Dubey, Indian J. Chem. 56B, 96 (2017)

    Google Scholar 

  40. D. Srikrishna, P.K. Dubey, New J. Chem. 41, 5168 (2017)

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

  1. Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally, Hyderabad, Telangana, 500 085, India

    Devulapally Srikrishna & Pramod Kumar Dubey

Authors
  1. Devulapally Srikrishna
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pramod Kumar Dubey
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Devulapally Srikrishna.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Srikrishna, D., Dubey, P.K. 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. Res Chem Intermed 44, 4455–4468 (2018). https://doi.org/10.1007/s11164-018-3397-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3397-x

Keywords

Search

Navigation