Skip to main content
SpringerLink
Log in

A facile, regioselective synthesis of pyrazolo[1, 5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their anti-inflammatory and anti-cancer activities

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An environmentally benign, simple, efficient, and convenient route is described for the synthesis of novel pyrazolo[1,5-a]pyrimidine derivatives under ultrasound irradiation assisted by KHSO4 in aqueous medium. 3-(4-Methoxyphenyl)-3-oxopropanenitrile reacted with hydrazine hydrate in refluxing ethanol to give 5-(4-methoxyphenyl)-1H-pyrazol-3-amine. Condensation of 3-aminopyrazoles with formylated active proton compounds furnished pyrazolopyrimidines in high to excellent yield. The chemical structure and regioselectivity of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, and mass spectral data. X-ray crystallographic study of a selected compound was performed. Furthermore, these synthesized compounds were screened for their anti-inflammatory and anti-cancer activity and the results were promising. The major advantages of this protocol afford high yields, operational simplicity, short reaction times, and devoid of harsh reaction conditions.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Elnagdi MH, Elmoghayar MRH, Elgemeie GEH (1987) Adv Heterocycl Chem 41:319

    Article  CAS  Google Scholar 

  2. Regan AC (2008) Pyrazolo[1,5-c]pyrimidine (73). In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) Comprehensive heterocyclic chemistry III, vol 11. Elsevier, Oxford, p 577

    Google Scholar 

  3. Youssef S (1997) Monatsh Chem 128:493

    Article  Google Scholar 

  4. Kandeel ZE, Hafez EA, Sleim MA, Abdelatif FM, Elnagdi MH (1995) Heteroat Chem 6:305

    Article  CAS  Google Scholar 

  5. Stepaniuk OO, Matviienko VO, Kondratov IS, Vitruk IV, Tolmachev AO (2012) Synthesis 45:925

    Google Scholar 

  6. Kalita U, Kaping S, Nellanant J, Helissey P, Vishwakarma JN (2014) Heteroletters 4:137

    Google Scholar 

  7. Devi AS, Kaping S, Vishwakarma JN (2015) Mol Divers 19:759

    Article  CAS  Google Scholar 

  8. Kaping S, Boiss I, Singha LI, Helissey P, Vishwakarma JN (2015) Mol Divers. doi:10.1007/s11030-015-9639-6

    Google Scholar 

  9. Petrov AA, Emelina EE, Selivanov SI (2008) Russ J Org Chem 44:263

    Article  CAS  Google Scholar 

  10. Quiroga J, Mejia D, Insuasty B, Abonia R, Nogueras M, Sanchez A, Cobo J (2002) J Heterocycl Chem 39:51

    Article  CAS  Google Scholar 

  11. Aggarwal R, Sumran G, Garg N, Aggarwal A (2011) Eur J Med Chem 46:3038

    Article  CAS  Google Scholar 

  12. Behbehani H, Ibrahim HM, Makhseed S, Mahmoud H (2011) Eur J Med Chem 46:1813

    Article  CAS  Google Scholar 

  13. Compton DR, Carlson KE, Katzenellenbogen JA (2004) J Med Chem 17:5872

    Article  Google Scholar 

  14. Mokhtara M, Saleha TS, Basahel SN (2012) J Mol Catal A 353–354:122

    Article  Google Scholar 

  15. Shaaban MR, Saleh TS, Farag AM (2007) Heterocycles 71:1765

    Article  CAS  Google Scholar 

  16. Behbehani H, Ibrahim HM, Makhseed S (2010) Arkivoc 2010(ii):267

    Google Scholar 

  17. Baluja S, Kachhadia N, Solanki A (2013) Open J Org Chem 1:1

    Google Scholar 

  18. Nagargoje D, Mandhane P, Shingote S, Badadhe P, Gill C (2012) Ultrason Sonochem 19:94

    Article  CAS  Google Scholar 

  19. Singh BS, Lobo HR, Pinjari DV, Jarag KJ, Pandit AB, Shankarling GS (2013) Ultrason Sonochem 20:287

    Article  CAS  Google Scholar 

  20. Jarag KJ, Pinjari DV, Pandit AB, Shankarling GS (2011) Ultrason Sonochem 18:617

    Article  CAS  Google Scholar 

  21. Banitaba SH, Safari J, Khalili SD (2013) Ultrason Sonochem 20:401

    Article  CAS  Google Scholar 

  22. Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi HR, Mirzaei P (2010) Ultrason Sonochem 17:447

    Article  CAS  Google Scholar 

  23. Khosropour AR (2008) Ultrason Sonochem 15:659

    Article  CAS  Google Scholar 

  24. Gopalsamy A, Ciszewski G, Shi M, Berger D, Hu Y, Lee F, Feldberg L, Frommer E, Kim S, Collins K, Wojciechowicz, Mallon R (2009) Bioorg Med Chem Lett 19:6890

    Article  CAS  Google Scholar 

  25. Chanda K, Dutta MC, Karim E, Vishwakarma JN (2004) J Indian Chem Soc 81:791

    CAS  Google Scholar 

  26. Radl S, Blahovcova M, Tkadlecová M, Havlicek J (2010) Heterocycles 80:1359

    Article  CAS  Google Scholar 

  27. Alam A, Imliwati L, Rapthap C, Singh V (2001) Indian J Exp Biol 39:201

    CAS  Google Scholar 

  28. Ferrari M, Fomasiero MC, Isetta AM (1990) J Immunol Methods 131:165

    Article  CAS  Google Scholar 

  29. Singh A, Malhotra S, Subban R (2008) Int J Integr Biol 3:57

    CAS  Google Scholar 

  30. Khan FH (2009) The elements of Immunology. Pearson education, India

    Google Scholar 

  31. Ahmad F, Khan R, Rasheed S (1992) J Islam Acad Sci 5:111

    Google Scholar 

  32. Kang OH, Chae HS, Oh YC, Choi JG, Lee YS, Jang HJ, Kim JH, Kim YC, Sohn DH, Park H, Kwon DY (2008) Am J Chin Med 36:913

    Article  CAS  Google Scholar 

  33. Mantovani NV, Germano G, Marchesi F, Locatelli M, Biswas SK (2011) Eur J Immunol 41:2522

    Article  CAS  Google Scholar 

  34. Freshney RI (2010) Culture of animal cells: a manual of basic technique and specialized applications, 6th edn. Wiley, New Jersey, p 373

    Book  Google Scholar 

  35. Lai SC, Peng WH, Huang SC, Ho YL, Huang JH, Lai Z, Chang Y (2009) Am J Chin Med 37:573

    Article  CAS  Google Scholar 

  36. Houwen B (2000) Lab Hematol 6:1

    Google Scholar 

Download references

Acknowledgments

Authors wish to thank Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University for providing infrastructure for the execution of this work. Authors also wish to express their gratitude to IIT, Guwahati, Tezpur University, Tezpur, SAIF-NEHU, Shillong and SAIF-CDRI, Lucknow. Our thanks are also due to the Department of Biotechnology (DBT), Government of India for a research grant. SK thanks NER-BPMC-DBT, New Delhi for a research fellowship.

Author information

Authors and Affiliations

  1. Organic Research Lab., Department of Chemical Science, Assam Don Bosco University, Guwahati, 781017, Assam, India

    Shunan Kaping, Utpalparna Kalita & Jai Narain Vishwakarma

  2. Department of Biotechnology, St. Anthony’s College, Shillong, 793001, India

    Melboureen Sunn & Laishram Indira Singha

Authors
  1. Shunan Kaping
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Utpalparna Kalita
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Melboureen Sunn
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Laishram Indira Singha
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jai Narain Vishwakarma
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jai Narain Vishwakarma.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1666 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaping, S., Kalita, U., Sunn, M. et al. A facile, regioselective synthesis of pyrazolo[1, 5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their anti-inflammatory and anti-cancer activities. Monatsh Chem 147, 1257–1276 (2016). https://doi.org/10.1007/s00706-015-1638-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1638-x

Keywords

Search

Navigation