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International Journal of Medicinal Chemistry
Volume 2011, Article ID 678101, 11 pages
http://dx.doi.org/10.1155/2011/678101
Research Article

Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates

1Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz 71345, Iran
2Department of Parasitology, Faculty of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran
3Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran

Received 18 May 2011; Revised 29 June 2011; Accepted 13 July 2011

Academic Editor: Stewart Schneller

Copyright © 2011 Zahra Rezaei et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Engel, “Phosphonates as analogues of natural phosphates,” Chemical Reviews, vol. 77, no. 3, pp. 349–367, 1977. View at Google Scholar · View at Scopus
  2. J. Hiratake and J. Oda, “Aminophosphonic and aminoboronic acids as key elements of a transition state analogue inhibitor of enzymes,” Bioscience, Biotechnology and Biochemistry, vol. 61, no. 2, pp. 211–218, 1997. View at Google Scholar · View at Scopus
  3. K. Moonen, I. Laureyn, and C. V. Stevens, “Synthetic methods for azaheterocyclic phosphonates and their biological activity,” Chemical Reviews, vol. 104, no. 12, pp. 6177–6215, 2004. View at Publisher · View at Google Scholar · View at Scopus
  4. F. Palacios, C. Alonso, and J. M. de los Santos, “β-phosphono- and phosphinopeptides derived from β-amino-phosphonic and phosphinic acids,” Current Organic Chemistry, vol. 8, no. 15, pp. 1481–1496, 2004. View at Publisher · View at Google Scholar · View at Scopus
  5. K. A. Schug and W. Lindner, “Noncovalent binding between guanidinium and anionic groups: focus on biological- and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues,” Chemical Reviews, vol. 105, no. 1, pp. 67–113, 2005. View at Publisher · View at Google Scholar · View at Scopus
  6. E. K. Baylis, C. D. Campbell, and J. G. Dingwall, “1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids,” Journal of the Chemical Society, Perkin Transactions 1, pp. 2845–2853, 1984. View at Google Scholar · View at Scopus
  7. D. Ouimette and M. Coffey, “Comparative antifungal activity of four phosphonate compounds against isolates of nine Phytophthora species,” Phytopathology, vol. 79, no. 7, pp. 761–767, 1989. View at Google Scholar
  8. S. Yang, X. W. Gao, C. L. Diao et al., “Synthesis and antifungal activity of novel chiral α-aminophosphonates containing fluorine moiety,” Chinese Journal of Chemistry, vol. 24, no. 11, pp. 1581–1588, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. B. S. Kumar, A. U. R. Sankar, C. Suresh Reddy, S. K. Nayak, and C. Naga Raju, “Synthesis, and antimicrobial activity of 2,10-dichloro-6- substituted aminobenzyl-12H-dibenzo [d, g][1,3,2]dioxaphosphocin- 6-oxides,” Arkivoc, vol. 2007, no. 13, pp. 155–166, 2007. View at Google Scholar · View at Scopus
  10. S. S. Sonar, S. A. Sadaphal, V. B. Labade, B. B. Shingate, and M. S. Shingare, “An efficient synthesis and antibacterial screening of novel oxazepine α-aminophosphonates by ultrasound approach,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 185, no. 1, pp. 65–73, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. M. J. Bloemink, J. J. H. Diederen, J. P. Dorenbos, R. J. Heetebrij, B. K. Keppler, and J. Reedijk, “Calcium ions do accelerate the DNA binding of new antitumor-active platinum aminophosphonate complexes,” European Journal of Inorganic Chemistry, no. 10, pp. 1655–1657, 1999. View at Google Scholar · View at Scopus
  12. L. Jin, B. Song, G. Zhang et al., “Synthesis, X-ray crystallographic analysis, and antitumor activity of N-(benzothiazole-2-yl)-1-(fluorophenyl)-O,O-dialkyl-α-aminophosphonates,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 6, pp. 1537–1543, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. X. Rao, Z. Song, and L. He, “Synthesis and antitumor activity of novel α-aminophosphonates from diterpenic dehydroabietylaminer,” Heteroatom Chemistry, vol. 19, no. 5, pp. 512–516, 2008. View at Publisher · View at Google Scholar · View at Scopus
  14. Y. Xu, K. Yan, B. Song et al., “Synthesis and antiviral bioactivities of α-aminophosphonates containing alkoxyethyl moieties,” Molecules, vol. 11, no. 9, pp. 666–676, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. M. R. Saidi and N. Azizi, “A new protocol for a one-pot synthesis of α-amino phosphonates by reaction of imines prepared in situ with trialkylphosphites,” Synlett, no. 8, pp. 1347–1349, 2002. View at Google Scholar · View at Scopus
  16. B. C. Ranu, A. Hajra, and U. Jana, “General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using indium(III) chloride as a catalyst,” Organic Letters, vol. 1, no. 8, pp. 1141–1143, 1999. View at Google Scholar · View at Scopus
  17. A. Manjula, B. V. Rao, and P. Neelakantan, “One-pot synthesis of α-aminophosphonates: an inexpensive approach,” Synthetic Communications, vol. 33, no. 17, pp. 2963–2969, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. C. Qian and T. Huang, “One-pot synthesis of α-amino phosphonates from aldehydes using lanthanide triflate as a catalyst,” Journal of Organic Chemistry, vol. 63, no. 12, pp. 4125–4128, 1998. View at Publisher · View at Google Scholar · View at Scopus
  19. S. Kumar, S. C. Taneja, M. S. Hundal, and K. K. Kapoor, “One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina,” Tetrahedron Letters, vol. 49, no. 14, pp. 2208–2212, 2008. View at Publisher · View at Google Scholar · View at Scopus
  20. S. Chandrasekhar, S. J. Prakash, V. Jagadeshwar, and C. Narsihmulu, “Three component coupling catalyzed by TaCl5-SiO2: synthesis of α-amino phosphonates,” Tetrahedron Letters, vol. 42, no. 32, pp. 5561–5563, 2001. View at Publisher · View at Google Scholar · View at Scopus
  21. T. Akiyama, M. Sanada, and K. Fuchibe, “Bronsted acid-mediated synthesis of α-amino phosphonates under solvent-free conditions,” Synlett, no. 10, pp. 1463–1464, 2003. View at Google Scholar · View at Scopus
  22. K. Manabe and S. Kobayashi, “Facile synthesis of α-amino phosphonates in water using a Lewis acid- surfactant-combined catalyst,” Chemical Communications, no. 8, pp. 669–670, 2000. View at Google Scholar · View at Scopus
  23. H. J. Ha and G. S. Nam, “An efficient synthesis of anilinobenzylphosphonates,” Synthetic Communications, vol. 22, no. 8, pp. 1143–1148, 1992. View at Google Scholar · View at Scopus
  24. H. Firouzabadi, N. Iranpoor, and S. Sobhani, “Metal triflate-catalyzed one-pot synthesis of α-aminophosphonates from carbonyl compounds in the absence of solvent,” Synthesis, no. 16, pp. 2692–2696, 2004. View at Publisher · View at Google Scholar · View at Scopus
  25. S. Bhagat and A. K. Chakraborti, “An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate,” Journal of Organic Chemistry, vol. 72, no. 4, pp. 1263–1270, 2007. View at Publisher · View at Google Scholar · View at Scopus
  26. H. Firouzabadi and M. Jafarpour, “Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2·8H2O) as catalysts or reagents in organic synthesis,” Journal of the Iranian Chemical Society, vol. 5, no. 2, pp. 159–183, 2008. View at Google Scholar · View at Scopus
  27. S. Bhagat and A. K. Chakraborti, “Zirconium(IV) compounds as efficient catalysts for synthesis of α-aminophosphonates,” Journal of Organic Chemistry, vol. 73, no. 15, pp. 6029–6032, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. M. Hosseini-Sarvari, “TiO2 as a new and reusable catalyst for one-pot three-component syntheses of α-aminophosphonates in solvent-free conditions,” Tetrahedron, vol. 64, no. 23, pp. 5459–5466, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. Z. Rezaei, H. Firouzabadi, N. Iranpoor et al., “Design and one-pot synthesis of α-aminophosphonates and bis(α-aminophosphonates) by iron(III) chloride and cytotoxic activity,” European Journal of Medicinal Chemistry, vol. 44, no. 11, pp. 4266–4275, 2009. View at Publisher · View at Google Scholar · View at Scopus
  30. K. Rathinasamy, B. Jindal, J. Asthana, P. Singh, P. V. Balaji, and D. Panda, “Griseofulvin stabilizes microtubule dynamics, activates p53 and inhibits the proliferation of MCF-7 cells synergistically with vinblastine,” BMC Cancer, vol. 10, pp. 213–226, 2010. View at Publisher · View at Google Scholar · View at Scopus
  31. M. Syamala, “Recent progress in three-component reactions. An update,” Organic Preparations and Procedures International, vol. 41, no. 1, pp. 1–68, 2009. View at Publisher · View at Google Scholar · View at Scopus