Research on Chemical Intermediates

, Volume 44, Issue 5, pp 3475–3491 | Cite as

One-pot green synthesis and bio-assay of pyrazolylphosphonates

  • Gundluru Mohan
  • Sarva Santhisudha
  • Sudileti Murali
  • Nemallapudi Bakthavatchala Reddy
  • Gundala Sravya
  • Grigory V Zyryanov
  • Cirandur Suresh Reddy


An efficient one-pot synthesis of bioactive pyrazolylphosphonates is accomplished by the reaction of 3-methyl-1-phenyl-2-pyrazoline-5-one with various aryl aldehydes and diethyl phosphite in the presence of β-cyclodextrin (β-CD) as a catalyst. The compounds were tested for their anti-oxidant activity by DPPH and H2O2 radical scavenging assay and for anticancer activity against breast cancer (MCF-7), prostate cancer (DU-145) and lung cancer (A-549) cell lines with sulfarodamine-B (SRB) assay. Most of the synthesized compounds showed promising anti-oxidant activity and significant anticancer activity when compared with the standard drugs.


Pyrazolylphosphonates Green synthesis β-cyclodextrin Anti-oxidant activity Anticancer activity 



The authors are grateful to Prof. C. Devendranath Reddy, Department of Chemistry, S.V. University, Tirupati, for his helpful discussions and acknowledge the funding support from DST-SERB, New Delhi, India, through Project No. SB/S1/OC-96/2013, Dt. 05-11-2014. One of the authors Dr. S. Santhisudha expresses sincere thanks to the Science and Engineering Research Board (SERB), New Delhi, India, for providing financial assistance (DST No: PDF/2016/000102, Dt: 11-07-2016). The corresponding author, Prof. C. Suresh Reddy, being an associate member of Institute of Food Security and Sustainable Agriculture, University Malaysia Kelantan, Jeli Campus, Malaysia, expresses his sincere thanks to University Malaysia Kelantan for their timely encouragement in our research work.

Supplementary material

11164_2018_3319_MOESM1_ESM.doc (8.3 mb)
Supplementary material 1 (DOC 8527 kb)


  1. 1.
    G. Mohan, S. Santhisudha, N.M. Reddy, T. Sreekanth, S. Murali, C.S. Reddy, Monatshefte Chem. 148, 1843 (2017)CrossRefGoogle Scholar
  2. 2.
    G. Mohan, S. Santhisudha, K.M.K. Reddy, N.V. Reddy, T. Vijaya, C.S. Reddy, Heteroatom Chem. 27, 269 (2016)CrossRefGoogle Scholar
  3. 3.
    S. Santhisudha, S.H. Jayaprakash, G. Mohan, Y.N. Kumar, V. Suganthi, V.M. Srinivasan, C.S. Reddy, Comb. Chem. High Throughput Screen. 19, 290 (2016)CrossRefGoogle Scholar
  4. 4.
    S. Santhisudha, T. Sreekanth, S. Murali, M.A. Devi, C.S. Reddy, Card Hem Agents Med. Chem. 14, 167 (2017)Google Scholar
  5. 5.
    A.A. Quntar, R. Gallily, G. Katzavian, M. Srebnik, Eur. J. Pharmacol. 556, 9 (2007)CrossRefGoogle Scholar
  6. 6.
    P. Alexander, V.V. Krishnamurthy, E.J. Prisbe, J. Med. Chem. 39, 1321 (1996)CrossRefGoogle Scholar
  7. 7.
    B.S. Kumar, M.V. Reddy, G.C.S. Reddy, N.B. Reddy, C.S. Reddy, J. Heterocycl. Chem. 48, 221 (2011)CrossRefGoogle Scholar
  8. 8.
    M.B. Colovi, D.Z. Krsti, T.D.L. Pasti, A.M. Bondzic, V.M. Vasi, Curr. Neuropharm. 11, 315 (2013)CrossRefGoogle Scholar
  9. 9.
    M.A. Dhansay, P.W. Linder, R.G. Torrington, T.A. Modro, J. Phys. Org. Chem. 3, 248 (1990)CrossRefGoogle Scholar
  10. 10.
    G.C. Reddy, C.R. Rani, M.V. Reddy, C.S. Reddy, Arch. Pharm. Chem. Life Sci. 347, 819 (2014)CrossRefGoogle Scholar
  11. 11.
    M. Regitz, J. Heterocycl. Chem. 31, 663 (1994)CrossRefGoogle Scholar
  12. 12.
    A. Ansari, A. Ali, M. Asif, New J. Chem. 41, 16 (2017)CrossRefGoogle Scholar
  13. 13.
    H.S. Sohal, M. Kaur, R. Khare, K. Singh, Am. J. Org. Chem. 4, 21 (2014)Google Scholar
  14. 14.
    A.M. Farag, K.A.K. Ali, T.M.A. El-Debss, A.S. Mayhoub, A.E. Amr, N.A. Abdel-Hafez, M.M. Abdulla, Eur. J. Med. Chem. 45, 5887 (2010)CrossRefGoogle Scholar
  15. 15.
    M. Abdel-Aziz, G.E.A. Abuo-Rahma, A.A. Hassan, Eur. J. Med. Chem. 44, 3480 (2009)CrossRefGoogle Scholar
  16. 16.
    G.A. Perazzoli, M. Proto, M.A. Rossano, Atti Accad. Med. Lomb. 19, 431 (1964)Google Scholar
  17. 17.
    P.B.R. Kumar, S. Subramaniyan, K. Yamini, R. Suthakaran, Rasayan J. Chem. 4, 400 (2011)Google Scholar
  18. 18.
    J. Mu, Y. Shi, M. Yang, Z. Sun, X. Liu, B. Li, N. Sun, Molecules 21, 1 (2016)CrossRefGoogle Scholar
  19. 19.
    R. Lan, Q. Liu, P. Fan, S. Lin, S.R. Fernando, D. Mc Callion, R. Pertwee, A. Makriyannis, J. Med. Chem. 42, 769 (1999)CrossRefGoogle Scholar
  20. 20.
    R.W. Fries, D.P. Bohlken, B.V. Plapp, J. Med. Chem. 22, 356 (1979)CrossRefGoogle Scholar
  21. 21.
    R. Kenchappa, Y.D. Bodke, A. Chandrashekar, M.A. Sindhe, S.K. Peethambar, Arab. J. Chem. 10, S3895 (2017)CrossRefGoogle Scholar
  22. 22.
    S.M. Gomha, K. Khalil, H. Abdel-aziz, M. Abdalla, Heterocycles 91, 1763 (2015)CrossRefGoogle Scholar
  23. 23.
    M.D. Khidre, H.M. Abou-Yousef, M. Refat, H. Mahran, Phosphorus Sulfur Silicon Relat. Elem. 177, 647 (2002)CrossRefGoogle Scholar
  24. 24.
    S.R. Kang, Y.R. Lee, Mol Divers. 19, 293 (2015)CrossRefGoogle Scholar
  25. 25.
    N. Basavegowda, K. Mishra, Y.R. Lee, New J. Chem. 39, 972 (2015)CrossRefGoogle Scholar
  26. 26.
    R. Breslow, S.D. Dong, Chem. Rev. 98, 1997 (1998)CrossRefGoogle Scholar
  27. 27.
    K. Konkala, R. Chowrasia, P.S. Manjari, N.L.C. Domingues, R. Katla, RSC Adv. 6, 43339 (2016)CrossRefGoogle Scholar
  28. 28.
    V.P. Kumar, M. Narender, R. Sridhar, Y.V.D. Nageswar, K.R. Rao, Synth. Comm. 37, 4331 (2007)CrossRefGoogle Scholar
  29. 29.
    K. Kanagaraj, K. Pitchumani, J. Org. Chem. 78, 744 (2013)CrossRefGoogle Scholar
  30. 30.
    A. Kumar, V. Tripathi, P. Kumar, Green Chem. 13, 51 (2011)CrossRefGoogle Scholar
  31. 31.
    V.P. Kumar, V.P. Reddy, R. Sridhar, B. Srinivas, M. Narender, K.R. Rao, J. Org. Chem. 73, 1646 (2008)CrossRefGoogle Scholar
  32. 32.
    N.S. Krishnaveni, K. Surendra, V.P. Kumar, B. Srinivas, C.S. Reddy, K.R. Rao, Tetrahedron Lett. 46, 4299 (2005)CrossRefGoogle Scholar
  33. 33.
    C.W. Choi, S.C. Kim, S.S. Hwang, B.K. Choi, H.J. Ahn, M.Y. Lee, S.H. Park, S.K. Kim, Plant Sci. 163, 1161 (2002)CrossRefGoogle Scholar
  34. 34.
    G.C. Yen, H.Y.J. Chen, Agric. Food Chem. 43, 27 (1995)CrossRefGoogle Scholar
  35. 35.
    P. Skehan, R. Storeng, D. Scudiero, A. Monks, I. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, M.R. Boyd, J. Nat. Cancer Inst. 82, 1107 (1990)CrossRefGoogle Scholar

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

Authors and Affiliations

  1. 1.Department of ChemistrySri Venkateswara UniversityTirupatiIndia
  2. 2.Department of ChemistryDravidian UniversityKuppamIndia
  3. 3.Department of Organic and Biomolecular Chemistry, Chemical Engineering InstituteUral Federal UniversityYekaterinburgRussian Federation
  4. 4.I.Ya. Postovskiy Institute of Organic SynthesisUral Division of the Russian Academy of SciencesYekaterinburgRussian Federation

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