165
Views
7
CrossRef citations to date
0
Altmetric
Short Communication

A convenient one-pot synthesis of 1-hydroxymethylene-1,1-bisphosphinic acids

ORCID Icon, , ORCID Icon, , ORCID Icon &
Pages 323-325 | Received 28 Sep 2018, Accepted 15 Oct 2018, Published online: 10 Dec 2018

References

  • Russell, R. G. Bisphosphonates: The First 40 Years. Bone 2011, 49, 2–19.
  • Lin, J. H. Bisphosphonates: A Review of Their Pharmacokinetic Properties. Bone 1996, 18, 75–85.
  • Monteil, M.; Migianu-Griffoni, E.; Sainte-Catherine, O.; Di Benedetto, M.; Lecouvey, L. Bisphosphonate Prodrugs: synthesis and Biological Evaluation in HuH7 Hepatocarcinoma Cells. Eur. J. Med. Chem. 2014, 77, 56–64.
  • Webster, M. R.; Kamat, C.; Connis, N.; Zhao, M.; Weeraratna, A. T.; Rudek, M. A.; Hann, C. L.; Freel, C. L. Bisphosphonamidate Clodronate Prodrug Exhibits Selective Cytotoxic Activity against Melanoma Cell Lines. Mol. Cancer Ther. 2014, 13, 297–306.
  • Abdelkarim, M.; Guenin, E.; Sainte-Catherine, O.; Vintonenko, N.; Peyri, N.; Perret, G. Y.; Crepin, M.; Khatib, A.-M.; Lecouvey, M.; Di Benedetto, M. New Symmetrically Esterified m-Bromobenzyl Non-Aminobisphosphonates Inhibited Breast Cancer Growth and Metastases. PLoS One. 2009, 4, e4685
  • Turhanen, P. A.; Ahlgren, M. J.; Järvinen, T.; Vepsäläinen, J. Bisphosphonate Prodrugs. Selective Synthesis of (1-Hydroxyethylidene)-1,1-Bisphosphonate Partial Esters. Synthesis 2001, 2001, 0633–0637.
  • Vepsäläinen, J. Bisphosphonate prodrugs. Curr. Med. Chem. 2002, 9, 1201–1208.
  • Tanaka, Y.; Iwasaki, M.; Murata-Hirai, K.; Matsumoto, K.; Hayashi, K.; Okamura, H.; Sugie, T.; Minato, N.; Morita, C. T.; Toi, M. Anti-Tumor Activity and Immunotherapeutic Potential of a Bisphosphonate Prodrug. Sci. Rep. 2017, 7, 1–14.
  • Migianu, E.; Mallard, I.; Bouchemal, N.; Lecouvey, L. One-Pot Synthesis of 1-Hydroxymethylene-1,1-Bisphosphonate Partial Esters. Tetrahedron Lett. 2004, 45, 4511–4513.
  • Monteil, M.; Guenin, E.; Migianu, E.; Lutomski, D.; Lecouvey, L. Bisphosphonate Prodrugs: synthesis of New Aromatic and Aliphatic 1-Hydroxy-1,1-Bisphosphonate Partial Esters. Tetrahedron 2005, 61, 7528–7537.
  • David, T.; Křečková, P.; Kotek, J.; Kubíček, V.; Lukeš, I. 1-hydroxy-1,1-Bis(H-Phosphinates): Synthesis, Stability, and Sorption Properties. Heteroatom Chem. 2012, 23, 195–201.
  • David, T.; Procházková, S.; Kotek, J.; Kubíček, V.; Hermann, P.; Lukeš, I. Aminoalkyl-1,1-Bis(phosphinic Acids): Stability, Acid-Base, and Coordination Properties. Eur. J. Inorg. Chem. 2014, 2014, 4357–4368.
  • Kaboudin, B.; Ezzati, A.; Faghihi, M. R.; Barati, A.; Kazemi, F.; Abdollahi, H.; Yokomatsu, T. Hydroxy-Bisphosphinic Acids: Synthesis and Complexation Properties with Transition Metals and Lanthanide Ions in Aqueous Solution. J. Iran. Chem. Soc. 2016, 13, 747–752.
  • Kašpárek, F. 1-Hydroxy-Alkan-1,1-Bis-Phosphinsäuren. Monatsh. Chem. 1969, 100, 2013–2018.
  • Lecouvey, M.; Mallard, I.; Bailly, T.; Burgada, R.; Leroux, Y. A Mild and Efficient One-Pot Synthesis of 1-Hydroxymethylene-1,1-Bisphosphonic Acids. Preparation of New Tripod Ligands. Tetrahedron Lett. 2001, 42, 8475–8478.
  • Dussart, J.; Deschamp, J.; Monteil, M.; Gager, O.; Migianu-Griffoni, E.; Lecouvey, M. A General Protocol for the Synthesis of H-α-Hydroxyphosphinates. Synthesis. 2018. Accepted manuscript. doi: 10.1055/s-0037-1610274
  • Deprèle, S.; Montchamp, J.-L. Y. Triethylborane-Initiated Room Temperature Radical Addition of Hypophosphites to Olefins: Synthesis of Monosubstituted Phosphinic Acids and Esters. J. Org. Chem. 2001, 66, 6745–6755.
  • Vang, T.; Xie, Y.; Liu, W. H.; Vidović, D.; Liu, Y.; Wu, S.; Smith, D. H.; Rinderspacher, A.; Chung, C.; Gong, G.; et al. Inhibition of Lymphoid Tyrosine Phosphatase by Benzofuran Salicylic Acids. J. Med. Chem. 2011, 54, 562–571.
  • Niemi, R.; Turhanen, P. A.; Vepsäläinen, J.; Taipale, H.; Järvinen, T. Bisphosphonate Prodrugs: synthesis and in Vitro Evaluation of Alkyl and Acyloxymethyl Esters of Etidronic Acid as Bioreversible Prodrugs of Etidronate. Eur. J. Pharm. Sci. 2000, 11, 173–180.
  • Griffiths, D. V.; Jamali, H. A. R.; Tebby, J. C. Reactions of Phosphites With Acid Chlorides. Phosphite Attack at the Carbonyl Oxygen of α-Ketophosphonates. Phosphorus Sulfur Silicon Relat. Elem. 1981, 11, 95–99.
  • Kaushik, M. P.; Gupta, A. K.; Lal, B.; Vaidyanathaswamy, R. Unusual Reaction of Triethylphosphite with Pyridoyl Chlorides. Phosphorus Sulfur Silicon Relat. Elem. 1992, 71, 175–177.
  • Dussart, J.; Guedeney, N.; Deschamp, J.; Monteil, M.; Gager, O.; Legigan, T.; Migianu-Griffoni, E.; Lecouvey, M. A Convenient Synthetic Route towards H-Bisphosphinates. Org. Biomol. Chem. 2018, 16, 6969–6979.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.