Skip to main content
SpringerLink
Log in

Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates

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

Abstract

A simple and effective green method has been developed for the synthesis of a series of novel bis α-aminophosphonate derivatives (4a–j) by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR, 1H, 13C, 31P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H2O2 methods and molecular docking studies. The compounds 4d and 4h exhibited the highest radical scavenging activity in the DPPH method, while compounds 4a, 4e and 4f showed good NO scavenging activity. The compound 4g showed remarkably higher H2O2 scavenging activity than even the standard ascorbic acid, and compound 4h has stronger inhibiting activity on DNA gyrase enzyme.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. R. Hirschmann, A.B. Smith, C.M. Taylor, P.A. Benkovic, S.D. Taylor, K.M. Yager, P.A. Sprengler, S.J. Benkovic, Science 265, 234 (1994)

    Article  CAS  PubMed  Google Scholar 

  2. W. Allen Fuhrer, B. Tuck, R. Wade, J.M. Wood, J. Med. Chem. 32, 1652 (1989)

    Article  PubMed  Google Scholar 

  3. E.W. Logusch, D.M. Walker, J.F. McDonald, G.C. Leo, J.E. Franz, J. Org. Chem. 53, 4069 (1988)

    Article  CAS  Google Scholar 

  4. P.P. Giannousis, P.A. Bartlett, J. Med. Chem. 30, 1603 (1987)

    Article  CAS  PubMed  Google Scholar 

  5. M. Emgenbroich, G.A. Wulff, Chem. Eur. J. 9, 4106 (2003)

    Article  CAS  PubMed  Google Scholar 

  6. K. Senten, L. Danie, P. Var der Veken, I. De Meester, A.M. Lambeir, S. Scharpe, A. Haemers, K. Augustyns, J. Comb. Chem. 5, 336 (2003)

    Article  CAS  PubMed  Google Scholar 

  7. B. Stowasser, K.H. Budt, J.Q. Li, A. Peyman, D. Ruppert, Tetrahedron Lett. 1992(33), 6625 (1992)

    Article  Google Scholar 

  8. D.V. Patel, K. Rielly-Gauvin, D.E. Ryono, Tetrahedron Lett. 31, 5587 (1990)

    Article  CAS  Google Scholar 

  9. S.A. Beers, C.F. Schwender, D.A. Loughney, E. Malloy, K. Demarest, J. Jordan, Bioorg. Med. Chem. 4, 1693 (1996)

    Article  CAS  PubMed  Google Scholar 

  10. T.R. Burke, J.J. Barchi, C. George, G. Wolf, S.E. ShoelsonYan, J. Med. Chem. 38, 1386 (1995)

    Article  CAS  PubMed  Google Scholar 

  11. F.R. Atherton, C.H. Hassall, R.W. Lambert, J. Med. Chem. 29, 29 (1986)

    Article  CAS  PubMed  Google Scholar 

  12. B.M. Rothschild, L.D. Martin, G. Lev, H. Bercovier, C. Greenblatt, H. Donoghue, M. Spigelman, D. Brittain, Clin. Infect. Dis. 33, 305 (2001)

    Article  CAS  PubMed  Google Scholar 

  13. A. Peyman, K.H. Budt, J.S. Paning, B. Stowasser, D. Ruppert, Tetrahedron Lett. 33, 4549 (1992)

    Article  CAS  Google Scholar 

  14. J.A. Sikosrki, M.J. Miller, D.S. Braccolino, Phosphorus Sulfur Silicon Relat. Elem. 76, 375 (1993)

    Google Scholar 

  15. B. Stowasser, K.H. Budt, A. Peyman, D. Ruppert, Tetrahedron Lett. 33, 6625 (1992)

    Article  CAS  Google Scholar 

  16. J.H. Meyer, P.A. Barlett, J. Am. Chem. Soc. 120, 4600 (1998)

    Article  CAS  Google Scholar 

  17. Z. Rezaei, H. Firouzabadi, N. Iranpoor, A. Ghaderi, M.R. Jafari, A.A. Jafari, H.R. Zare, Eur. J. Med. Chem. 44, 4266 (2009)

    Article  CAS  PubMed  Google Scholar 

  18. Z. Rezaei, S. Khabnadideh, K. Zomorodian, K. Pakshir, S. Nadali, N. Mohtashami, E. FaghihMirzaei, Int. J. Med. Chem. 11, 468 (2011)

    Google Scholar 

  19. S.N. Ali, S. Zakir, M. Patel, M. Farooqui, Eur. J. Med. Chem. 50, 39 (2012)

    Article  CAS  PubMed  Google Scholar 

  20. L. Maier, H. Spoerri, Phosphorus Sulfur Silicon Relat. Elem. 61, 69 (1991)

    Article  CAS  Google Scholar 

  21. J. Emsley, D. Hall, Chemistry of Phosphorus, vol. 9 (Harper and Row, London, 1976), p. 494

    Google Scholar 

  22. Q. Wang, M. Zhu, R. Zhu, L. Lu, C. Yuan, S. Xing, Y. Mei, Q. Hang, Eur. J. Med. Chem. 49, 354 (2012)

    Article  CAS  PubMed  Google Scholar 

  23. L. Maier, Phosphorus, Sulfur Silicon Relat. Elem. 53, 43 (1990)

    Article  CAS  Google Scholar 

  24. A.K. Bhattacharya, D.S. Raut, C. Rana, I.K. Polankia, M.S. Khan, S. Iramb, Eur. J. Med. Chem. 66, 146 (2013)

    Article  CAS  PubMed  Google Scholar 

  25. D.P. Allais, A. Simon, B. Bennini, A.J. Chulia, M. Kaouadji, C. Delage, Phytochemistry 30, 3309 (1991)

    Article  Google Scholar 

  26. T.J.A. Ewing, S. Makino, A.G. Skillman, I.D. Kuntz, J. Comput. Aided Mol. Des. 15, 411 (2001)

    Article  CAS  PubMed  Google Scholar 

  27. G.M. Morris, D.S. Doodsell, R.S. Holliday, R. Huey, W.E. Hart, R.K. Belew, A.J. Olson, J. Comput. Chem. 19, 1639 (1998)

    Article  CAS  Google Scholar 

  28. M. Kontoyianni, L.M. McClellan, G.S. Sokol, J. Med. Chem. 47, 558 (2004)

    Article  CAS  PubMed  Google Scholar 

  29. S. Laschat, H. Kunz, Synthesis 90, 56 (1992)

    Google Scholar 

  30. J. Zou, J. Pol. Chem. 55, 643 (1981)

    Google Scholar 

  31. K.A. Petov, V.A. Chauzov, T.S. Erkhina, Chem. Abstr. 82, 449 (1975)

    Google Scholar 

  32. V. Jagodic, Croatica Chem. Acta. 48, 325 (1976)

    CAS  Google Scholar 

  33. H. Firouzabadi, N. Iranpoor, S. Sobhani, Synthesis 86, 2692 (2004)

    Article  CAS  Google Scholar 

  34. T. Akiyama, M. Sanada, K. Fuchide, Synlett 67, 1463 (2003)

    Article  Google Scholar 

  35. B.V. Subba Reddy, A.S. Krishna, A.V. Ganesh, Tetrahedron Lett. 52, 1359 (2011)

    Article  CAS  Google Scholar 

  36. M.Z. Kassaee, F. Movahedi, H. Masrouri, Synlett 68, 1326 (2009)

    Article  CAS  Google Scholar 

  37. S. Bhagat, A.K. Chakraborti, J. Org. Chem. 73, 6029 (2008)

    Article  CAS  PubMed  Google Scholar 

  38. B. Kaboudin, H. Zahedi, Chem. Lett. 37, 540 (2008)

    Article  CAS  Google Scholar 

  39. J.S. Wieczorek, R. Gancarz, S. Bielecki, E. Grzys, J. Sarapuk, Phosphorus Sulfur Silicon 174, 119 (2001)

    Article  CAS  Google Scholar 

  40. J. Oleksyszin, V.P. Kukhar, H.R. Hudson, (eds.), Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, vol. 96 (Wiley, Chichester, 2000), p. 537

    Google Scholar 

  41. C. Qian, T. Huang, J. Org. Chem. 63, 4125 (1998)

    Article  CAS  Google Scholar 

  42. B.C. Ranu, A. Hajra, U. Jana, Org. Lett. 1, 1141 (1999)

    Article  CAS  Google Scholar 

  43. B.C. Ranu, A. Hajra, Green Chem. 4, 551 (2002)

    Article  CAS  Google Scholar 

  44. R. Ghosh, S. Maiti, A. Chakraborty, D. Maiti, J. Mol. Catal. A Chem. 53, 210 (2004)

    Google Scholar 

  45. S. Chandrasekhar, S.J. Prakash, S.J.V. Jagadeswar, C. Narsihmulu, Tetrahedron Lett. 42, 5561 (2001)

    Article  CAS  Google Scholar 

  46. J.S. Yadav, V.S. Reddy, S. Raj, K.B. Reddy, A.R. Prasad, Synthesis 46, 2277 (2001)

    Article  Google Scholar 

  47. P.P. Sun, Z.X. Hu, Z.H. Huang, Synth. Commun. 34, 4293 (2004)

    Article  CAS  Google Scholar 

  48. Z.P. Zhan, J.P. Li, Synth. Commun. 35, 2501 (2005)

    Article  CAS  Google Scholar 

  49. A. Heydari, A. Karimian, J. Ipaktschi, Tetrahedron Lett. 39, 6729 (1998)

    Article  CAS  Google Scholar 

  50. B. Kaboudin, Chem. Lett. 12, 880 (2001)

    Article  Google Scholar 

  51. B. Kaboudin, R. Nazari, Tetrahedron Lett. 42, 8211 (2001)

    Article  CAS  Google Scholar 

  52. B. Kaboudin, Tetrahedron Lett. 44, 1051 (2003)

    Article  CAS  Google Scholar 

  53. K. Manabe, S. Kobayashi, Chem. Commun. 75, 669 (2000)

    Article  Google Scholar 

  54. G. Lee, J.H. Park, J. Kang, J.K. Lee, Chem. Commun. 98, 1698 (2001)

    Article  CAS  Google Scholar 

  55. A. Saidi, N. Azizi, Synlett 104, 1347 (2002)

    Article  Google Scholar 

  56. T. Akiyama, K. Matsuda, K. Fuchibe, Synthesis 78, 206 (2005)

    Google Scholar 

  57. J.S. Yadav, B.V.S. Reddy, P. Sreedhar, Green Chem. 4, 436 (2002)

    Article  CAS  Google Scholar 

  58. X.J. Mu, M.Y. Lei, J.P. Zou, W. Zhang, Tetrahedron Lett. 78, 1125 (2006)

    Article  CAS  Google Scholar 

  59. M. Xia, Y.D. Lu, Ultrason. Sonochem. 15, 235 (2006)

    Google Scholar 

  60. D. Lafitte, V. Lamour, V. Tsvetkov, P.O. Makarov, A.A. Klich, M. Deprez, P. Moras, D. Briand, C. Gilli, Biochemistry 41, 7217 (2002)

    Article  CAS  PubMed  Google Scholar 

  61. S.K. Thaslim Basha, D. Subba Rao, G. Madhava, S. Thahir Basha, M. Nagalakshmi Devamma, S. Madhu Sudhana, A. Usha Rani, C. Naga Raju, Phosphorus Sulfur Silicon 190, 1064 (2015)

    Article  CAS  Google Scholar 

  62. K.V. Balakin, Y.A. Ivanenkov, A.V. Skorenko, Y.V. Nikolsky, N.P. Savchuk, A.A. Ivashchenko, J. Biomol. Screening. 9, 22 (2004)

    Article  CAS  Google Scholar 

  63. A. Hall, D. Parsonage, L.B. Poole, P.A. Karplus, J. Mol. Biol. 10, 194 (2010)

    Article  CAS  Google Scholar 

  64. J.P. Declercq, C. Evrard, A. Clippe, D.V. Stricht, A. Bernard, B. Knoops, J. Mol. Biol. 311, 751 (2001)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The authors express thanks to Prof. C. Devendranath Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, for his helpful discussions, and acknowledge the University Grants Commission (UGC), New Delhi, providing funding (BSR-RFSMS) to Mr. Shaik Mahammad Sadik [Letter no. F. 25-1/2014-15 (BSR)/7-187/2007(BSR), dated 13-03-2015]. One of the co-authors, Mr. G. Mohan (SRF), expresses his sincere thanks to DST-PURSE 2nd Phase Programme in S.V. University, Tirupati, funded by DST, New Delhi, India [17118-UGC-III(3)/DST-PURSE 2nd Phase/2017, Dt: 23-08-2018].

Author information

Authors and Affiliations

  1. Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, 517 502, India

    Shaik Mahammad Sadik, Sarva Santhisudha, Gundluru Mohan, Nadiveedhi Maheshwara Reddy, Poola Sree Lakshmi & Cirandur Suresh Reddy

  2. DST-PURSE Centre, Sri Venkateswara University, Tirupati, Andhra Pradesh, 517 502, India

    Gundluru Mohan

  3. Department of Biochemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, 517 502, India

    Allagadda Rajasekhar & Chippada Appa Rao

Authors
  1. Shaik Mahammad Sadik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sarva Santhisudha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gundluru Mohan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nadiveedhi Maheshwara Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Poola Sree Lakshmi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Allagadda Rajasekhar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Chippada Appa Rao
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Cirandur Suresh Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cirandur Suresh Reddy.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 3239 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sadik, S.M., Santhisudha, S., Mohan, G. et al. Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates. Res Chem Intermed 45, 1401–1420 (2019). https://doi.org/10.1007/s11164-018-3685-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3685-5

Keywords

Search

Navigation