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Hydroxy-bisphosphinic acids: synthesis and complexation properties with transition metals and lanthanide ions in aqueous solution

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Abstract

Treatment of acyl chlorides with a mixture of ammonium hypophosphite and hexamethyl disilazene gave 1-hydroxy-1,1-bisphosphinic acids. Acid dissociation constants (pKa) of 1-hydroxy-1,1-bisphosphinic acids were determined by the pH-potentiometric technique. Complexation properties of 1-hydroxy-1-phenylmethyl-1,1-bis(H-phosphinic acid) (HBPA 1) with Ca2+ as well as transition metals Fe2+, Ni2+, Cu2+, Cr3+ and lanthanide ions La3+, Gd3+ were studied in aqueous solution. The stabilizing ability of complexes of HBPA 1 with these ions in aqueous solutions was determined to show a significant difference in the complex stability due to the transition metals.

Graphical abstract

The coordination of 1-hydroxy-1,1-bis(H-phosphinic acid) to metals.

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References

  1. V.P. Kukhar, H.R. Hudson, in Aminophosphonic and Aminophosphinic Acids (Wiley, 2000)

  2. M. Collinsova, J. Jiracek, Curr. Med. Chem. 7, 629–647 (2000)

    Article  CAS  Google Scholar 

  3. R. Latajka, A. Krężel Mucha, M. Jewgiński, P. Kafarski, J. Mol. Struct. 877, 64–71 (2008)

    Article  CAS  Google Scholar 

  4. Y. Ye, M. Liu, J.L.-F. Kao, G.R. Marshall, Biopolymer 89, 72–85 (2008)

    Article  CAS  Google Scholar 

  5. J. Simecek, M. Schulz, J. Notni, J. Plutner, V. Kubicek, J. Havlickova, P. Hermann, Inorg. Chem. 51, 577–590 (2012)

    Article  CAS  Google Scholar 

  6. T. Kiss, E. Farakas, M. Jezowska-Bojczuk, H. Kozlowski, E Kowalik, J. Chem. Soc. Dalton Trans. 377–379 (1990)

  7. T. Kiss, M. Jezowska-Bojczuk, H. Kozlowski, P. Kafarski, K. Antczak, J. Chem. Soc. Dalton Trans. 2275–2279 (1991)

  8. I. Lukes, K. Bazakas, P. Hermann, P. Vojtisek, J. Chem. Soc. Dalton Trans. 939–944 (1992)

  9. P. Hermann, I. Lukes, J. Chem. Soc. Dalton Trans. 2605–2610 (1995)

  10. S. Vassiliou, A. Grabowiecka, P. Kosikowska, A. Yiotakis, P. Kafarski, L.J. Berlicki, Med. Chem. 51, 5736–5744 (2008)

  11. N. Gavande, I. Yamamoto, N.K. Salam, T.-H. Ai, P.M. Burden, G.A.R. Johnston, J.R. Hanrahan, M. Chebib, ACS Med. Chem. Lett. 2, 11–16 (2011)

    Article  CAS  Google Scholar 

  12. T.K. Olszewski, J. Galezowska, B. Boduszek, H. Kozlowski, Eur. J. Org. Chem. 3539–3546 (2007)

  13. S. Vassiliou, A. Grabowiecka, P. Kosikowska, A. Yiotakis, P. Kafarski, L. Berlicki, J. Med. Chem. 51, 5736–5744 (2008)

    Article  CAS  Google Scholar 

  14. C.J. Baron, K.J. Jankowski, R. Kataky, D. Parker, A.M. Randall, A. Harrison, J. Chem. Soc. Chem. Commun. 1739–1741 (1990)

  15. G. Tircso, A. Benyei, R. Kiraly, I. Lazar, R. Pal, E. Brucher, Eur. J. Inorg. Chem. 710–713 (2007)

  16. I. Lazar, A.D. Sherry, R. Ramasamy, E. Brucher, R. Kiraly, Inorg. Chem. 30, 5016–5019 (1991)

    Article  CAS  Google Scholar 

  17. J. Rohovec, M. Kyvala, P. Vojtisek, P. Hermann, I. Lukes, Eur. J. Inorg. Chem. 195–203 (2000)

  18. H. Fleisch, Bisphosphonates in Bone Disease, 4th edn. (Academic Press, London, 2000)

  19. A.L. Langston, M.K. Campbell, W.D. Fraser, G.S. MacLennan, P.L. Selby, S.H.J. Ralston, Bone. Miner. Res. 25, 20–31 (2010)

    Article  CAS  Google Scholar 

  20. D.V. Patel, K. Rielly-Gauvin, D.E. Ryono, C.A. Free, W.L. Rogers, S.A. Smith, J.M. DeForrest, R.S. Oehl, E.W. Petrillo Jr, J. Med. Chem. 38, 4557–4569 (1995)

    Article  CAS  Google Scholar 

  21. S.P. Luckman, F.P. Coxon, F.H. Ebetino, G.G. Russell, M.J. Rogers, J. Bone Miner. Res. 13, 1668–1678 (1998)

    Article  CAS  Google Scholar 

  22. E. van Beek, L. Cohen, I. Leroy, F. Ebetino, C. Lowik, S. Papapoulos, Bone 33, 805–811 (2007)

    Article  Google Scholar 

  23. H. Fleisch, Breast Cancer Res. 4, 30–34 (2002)

    Article  CAS  Google Scholar 

  24. M.A. Lopez-Olivo, N.A. Shah, G.P. Pratt, J.M. Risser, E. Symanski, M.E. Suarez-Almazor, Support. Care Cancer 20, 2985–2998 (2012)

    Article  Google Scholar 

  25. M. Katoh, J. Hiratake, H. Kato, J. Oda, Bioorg. Med. Chem. Lett. 6, 1437–1442 (1996)

    Article  CAS  Google Scholar 

  26. M. Drag, R. Grzywa, J. Oleksyszyn, Bioorg. Med. Chem. Lett. 17, 1516–1519 (2007)

    Article  CAS  Google Scholar 

  27. R. Grzywa, J. Oleksyszyn, G.S. Salvesen, M. Drag, Bioorg. Med. Chem. Lett. 20, 2497–2499 (2010)

    Article  CAS  Google Scholar 

  28. B. Kaboudin, N. As-Habei, Tetrahedron Lett. 44, 4243–4245 (2003)

    Article  CAS  Google Scholar 

  29. B. Kaboudin, T. Haruki, T. Yamagishi, T. Yokomatsu, Tetrahedron 63, 8199–8205 (2007)

    Article  CAS  Google Scholar 

  30. B. Kaboudin, T. Haruki, T. Yamagishi, T. Yokomatsu, Synthesis 3226–3232 (2007)

  31. B. Kaboudin, E. Jafari, J. Iran. Chem. Soc. 5, S97–S102 (2008)

    Article  CAS  Google Scholar 

  32. B. Kaboudin, F. Saadati, Tetrahedron Lett. 50, 1450–1452 (2009)

    Article  CAS  Google Scholar 

  33. B. Kaboudin, H. Haghighat, T. Yokomatsu, J. Org. Chem. 71, 6604–6606 (2006)

    Article  CAS  Google Scholar 

  34. B. Kaboudin, F. Saadati, T. Yokomatsu, Synlett. 1837–1840 (2010)

  35. B. Kaboudin, H. Haghighat, S. Alaie, T. Yokomatsu, Synlett. 23, 1965–1969 (2012)

  36. B. Kaboudin, F. Saadati, A. Golshan, H. Abdollahi, T. Yokomatsu, J. Chem. Eng. Data 56, 3651–3656 (2011)

    Article  CAS  Google Scholar 

  37. B. Kaboudin, K. Moradi, A. Barati, H. Abdollahi, J. Iran. Chem. Soc. 10, 763–770 (2013)

    Article  CAS  Google Scholar 

  38. T. David, P. Kreckova, J. Kotek, V. Kubicek, I. Lukes, Hetereoatom. Chem. 23, 195–201 (2012)

    Article  CAS  Google Scholar 

  39. M. Maeder, Y.M. Neuhold, Practical Data Analysis in Chemistry (Elsevier, Amsterdam, 2007)

    Google Scholar 

  40. C.H. Huang, J.R. Morrrow, Inorg. Chem. 48, 7237–7243 (2009)

    Article  CAS  Google Scholar 

  41. M.D. Cohen, E. Fischer, J. Chem. Soc. 3044–3052 (1962)

  42. L. Xu, S.J. Retting, C. Orvig, Inorg. Chem. 40, 3734–3738 (2001)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge support by the Institute for Advanced Studies in Basic Sciences (IASBS) Research Council under Grant No. G2014IASBS31101.

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Authors and Affiliations

  1. Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan, 45137-66731, Iran

    Babak Kaboudin, Ali Ezzati, Mohammad Reza Faghihi, Ali Barati, Foad Kazemi & Hamid Abdollahi

  2. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan

    Tsutomu Yokomatsu

Authors
  1. Babak Kaboudin
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  2. Ali Ezzati
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  3. Mohammad Reza Faghihi
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  4. Ali Barati
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  5. Foad Kazemi
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  6. Hamid Abdollahi
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  7. Tsutomu Yokomatsu
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Correspondence to Babak Kaboudin.

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Kaboudin, B., Ezzati, A., Faghihi, M.R. et al. Hydroxy-bisphosphinic acids: synthesis and complexation properties with transition metals and lanthanide ions in aqueous solution. J IRAN CHEM SOC 13, 747–752 (2016). https://doi.org/10.1007/s13738-015-0787-5

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  • DOI: https://doi.org/10.1007/s13738-015-0787-5

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