Skip to main content
SpringerLink
Log in

Straightforward multicomponent synthesis of pyrano[2,3-d]pyrimidine-2,4,7-triones in β-cyclodextrin cavity and evaluation of their anticancer activity

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

In the present study, we have developed an efficient and green method for the synthesis of pyrano[2,3-d]pyrimidine-2,4,7-triones employing β-cyclodextrin as a catalyst in aqueous media from substituted aldehydes, barbituric acid and meldrum acid. The reactions were performed under mild conditions to afford biologically active target molecules in excellent yields. All the synthesized compounds are evaluated for their in vitro anticancer activity against HePG-2 (Human liver cancer cell line) and MCF-7 (Human breast cancer cell line). Among them 4c, 4j, 4k, 4l and 4m were active and potent anticancer agents.

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

Similar content being viewed by others

References

  1. S. Maddila, R. Pagadala, S.B. Jonnalagadda, Lett. Org. Chem. 10, 693–714 (2013)

    Article  CAS  Google Scholar 

  2. S. Maddila, K. Naicker, M. Momin, S. Rana, S. Gorle, S.N. Maddila, Y. Kotaiah, M. Singh, S.B. Jonnalagadda, Med. Chem. Res. 25, 283–291 (2016)

    Article  CAS  Google Scholar 

  3. J. Delaney, E. Clarke, D. Hughes, M. Rice, Drug Discovery Today 11, 839–845 (2006)

    Article  PubMed  Google Scholar 

  4. K. Sharma, S. Jayakumar, M.S. Hundal, M.P. Mahajan, J. Chem. Soc., Perkin Trans. 1, 774 (2002)

    Article  CAS  Google Scholar 

  5. S. Sasaki, N. Cho, Y. Nara, M. Harada, S. Endo, N. Suzuki, S. Furuya, M. Fujino, J. Med. Chem. 46, 113 (2003)

    Article  CAS  PubMed  Google Scholar 

  6. L.H. Li, T.L. Wallace, K.A. Richard, D.E. Tracey, Cancer Res. 45, 532 (1985)

    CAS  PubMed  Google Scholar 

  7. N.R. Kamdar, D.D. Haveliwala, P.T. Mistry, S.K. Patel, Eur. J. Med. Chem. 45, 5056 (2010)

    Article  CAS  PubMed  Google Scholar 

  8. M.E. Abdel Fattah, A.H. Atta, I.I. Abdel Gawad, S.M. Mina, Orient. J. Chem. 20, 257 (2004)

    CAS  Google Scholar 

  9. M.M. Ghorab, A.Y. Hassan, Phosphorus, Sulfur Silicon Relat. Elem. 141, 251 (1998)

    Article  CAS  Google Scholar 

  10. O. Bruno, C. Brullo, A. Ranise, S. Schenone, F. Bondavalli, E. Barocelli, V. Ballabeni, M. Chiavarini, M. Tognolini, M. Impicciatore, Bioorg. Med. Chem. Lett. 11, 1397 (2001)

    Article  CAS  PubMed  Google Scholar 

  11. V.K. Akluwalia, M. Bala, Indian J. Chem. B 35B, 742 (1996)

    CAS  Google Scholar 

  12. H. Shamroukh, M.E.A. Zaki, E.M.H. Morsy, F.M. Abdel-Motti, F.M.E. Abdel-Megeid, Arch. Pharm. 340, 236 (2007)

    Article  CAS  Google Scholar 

  13. D. Kosk-Kosicka, I. Fomitcheva, M. M. Lopez. Biochemistry 35, 900 (1990)

    Article  Google Scholar 

  14. S.H. Kim, A.T. Pudzianowski, K.J. Leavitt et al., Bioorg. Med. Chem. Lett. 15, 1101 (2005)

    Article  CAS  PubMed  Google Scholar 

  15. D.M. Neumann, A. Cammarata, G. Backes, G.E. Palmer, B.S. Jursic, Bioorg. Med. Chem. 22, 813 (2014)

    Article  CAS  PubMed  Google Scholar 

  16. J.T. Bojarski, J.L. Mokrosz, H.J. Barton, M. H. Paluchowska. Adv Heterocycl Chem. 38, 229 (1985)

    Article  CAS  Google Scholar 

  17. D. Holy, I. Votruba, M. Masojidkova, G. Andrei, R. Snoeck et al., J. Med. Chem. 45, 1918–1929 (2002)

    Article  CAS  PubMed  Google Scholar 

  18. P. Andres, A. Marhold, J Fluorine Chem 77, 93–95 (1996)

    Article  CAS  Google Scholar 

  19. J.J. Reddick, S. Saha, J. Lee, J.S. Melnick, J. Perkins et al., Bioorg. Med. Chem. Lett. 11, 2245–2248 (2001)

    Article  CAS  PubMed  Google Scholar 

  20. H. Omar, H. Eman Mostafa, A. Neama, I. Sherien, M. Abd-Elmoez, Aus J Basic and Applied Sci 4, 27–36 (2010)

    Google Scholar 

  21. H.S. Basavaraja, K.V. Jayadevaiah, M.H. Mumtaz, M.M. Vijay Kumar, P. Basavaraj, J Pharm Sci Res 2, 5–12 (1989)

    Google Scholar 

  22. N.R. Penthala, A. Ketkar, K.R. Sekhar, M.L. Freeman, R.L. Eoff, R. Balusu, P.A. Crooks, Bioorg. Med. Chem. 23, 7226–7233 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. L.H. Li, T.L. Wallace, K.A. Richard, D.E. Tracey, Can. Res. 45, 532–538 (1985)

    CAS  Google Scholar 

  24. R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958–2975 (2014)

    Article  CAS  Google Scholar 

  25. S. Fu, L. Wanga, H. Dong, J. Yu, L. Xu, J. Xiao, Tetrahedron Lett. 57, 4533–4536 (2016)

    Article  CAS  Google Scholar 

  26. S.H. Saleh Azzam, M.A. Pasha, Tetrahedron Lett. 53, 7056–7059 (2012)

    Article  CAS  Google Scholar 

  27. H. Dandia, S.L. Gupta, S. Bhaskaran, Eur. Chem. Bull. 2(11), 836–841 (2013)

    CAS  Google Scholar 

  28. S. Ghorad, L.D. Mahalle, J.N. Khillare, M.R. Sangshetti, Bhosle, Catal Lett 147, 640–648 (2017)

    Article  CAS  Google Scholar 

  29. M.R. Bhosle, L.D. Khillare, S.T. Dhumal, R.A. Mane, Chinese Chem. Lett. 27, 370–374 (2016)

    Article  CAS  Google Scholar 

  30. M.R. Bhosle, L.D. Khillare, S.T. Dhumal, R.A. Mane, Lett. Org. Chem. 13, 148–155 (2016)

    Article  CAS  Google Scholar 

  31. T.J. Mosman, Immunol. Methods 65, 55–63 (1983)

    Article  Google Scholar 

  32. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, M.R. Boyd, Cancer Res. 48, 589–601 (1988)

    CAS  PubMed  Google Scholar 

  33. H. Domling, Chem. Rev. 106, 17 (2006)

    Article  CAS  PubMed  Google Scholar 

  34. D.J. Raman, M. Yus, Angew. Chem., Int. Ed. 44, 1602 (2005)

    Article  CAS  Google Scholar 

  35. R. Breslow, S.D. Dong, Chem. Rev. 98, 1997–2011 (1998)

    Article  CAS  PubMed  Google Scholar 

  36. Y. Cao, X. Xiao, R. Li, Q. Guo, J. Mol. Struct. 660, 73 (2003)

    Article  CAS  Google Scholar 

  37. R. Villalonga, R. Cao, A. Fragoso, Chem. Rev. 107, 3088 (2007)

    Article  CAS  PubMed  Google Scholar 

  38. F. Hapiot, S. Tilloy, E. Monflier, Chem. Rev. 106, 767 (2005)

    Article  CAS  Google Scholar 

  39. J. Szeijtli, Chem. Rev. 98, 1743 (1998)

    Article  Google Scholar 

  40. J. Heng-Bing, S. Dong-Po, S. Ming, L. Zhong, W. Le-Fu, Tetrahedron Lett. 46, 2517 (2005)

  41. B. Banerjee Ultrason Sonochem. 2017 Mar;35(Pt A):1–14

  42. M. Vidal, M. García-Arriagada, M.C. Rezende, M. Domínguez, Synthesis 48, 4246–4252 (2016)

    Article  CAS  Google Scholar 

  43. U. Qin, Schneider, J. Am. Chem. Soc. 138, 13119–13122 (2016)

    Article  CAS  PubMed  Google Scholar 

  44. Bubun Banerjee Ultrasonics Sonochemistry Volume 35, A. Part, March 2017, Pages 15–35

  45. N.G. Khaligh, F. Shirini, Ultrason Sonochem 20, 19–25 (2013)

    Article  CAS  PubMed  Google Scholar 

  46. N.G. Khaligh, F. Shirini Ultrason Sonochem 20, 26–31 (2013)

    Article  CAS  PubMed  Google Scholar 

  47. P. Nagargoje, S. Mandhane, P. Shingote, C.H. Badadhe, Gill, Ultrason Sonochem 19, 94–96 (2012)

    Article  CAS  PubMed  Google Scholar 

  48. F. Dang, N.Y. Enomoto, J.C. Hojo, K.J. Enpuku, Ultrason Sonochem 16, 649–654 (2009)

    Article  CAS  PubMed  Google Scholar 

  49. H.M. Cabral Marques, J. Hadgraft, I.W. Kellaway, W.J. Pugh, Int. J. Pharm. 63, 267–274 (1990)

    Article  CAS  Google Scholar 

  50. B.S. Londhe, U.R. Pratap, J.R. Mali, R.A. Mane, Bull. Korean Chem. Soc. 31, 2329 (2010)

    Article  CAS  Google Scholar 

  51. S. Sukumari, I.A. Azath, K. Pitchumani, Synlett, 2328–2332 (2012)

  52. S.N. Murthy, B. Madhav, A.V. Kumar, K.R. Rao, Y. V. D. Nageswar Helv. Chim. Acta 92, 2118–2124 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to Professor Ramrao A. Mane for his invaluable discussions and guidance. The authors are also thankful to Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad and Central Drug Research Institute (CDRI), Lucknow for providing necessary facilities and spectral analysis, respectively.

Author information

Authors and Affiliations

  1. Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, MS, 431004, India

    Manisha R. Bhosle, Pooja Andil, Diksha Wahul & Giribala M. Bondle

  2. Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, MS, 431004, India

    Aniket Sarkate

  3. Department of Pharmaceutical Chemistry, Durgamata Institute of Pharmacy, Dharmapuri, Parbhani-431401, MS, 431001, India

    Shailee V. Tiwari

Authors
  1. Manisha R. Bhosle
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pooja Andil
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Diksha Wahul
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Giribala M. Bondle
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Aniket Sarkate
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Shailee V. Tiwari
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Manisha R. Bhosle.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 249 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bhosle, M.R., Andil, P., Wahul, D. et al. Straightforward multicomponent synthesis of pyrano[2,3-d]pyrimidine-2,4,7-triones in β-cyclodextrin cavity and evaluation of their anticancer activity. J IRAN CHEM SOC 16, 1553–1561 (2019). https://doi.org/10.1007/s13738-019-01633-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01633-2

Keywords

Search

Navigation