Table of Contents Author Guidelines Submit a Manuscript
International Journal of Medicinal Chemistry
Volume 2015, Article ID 738202, 8 pages
http://dx.doi.org/10.1155/2015/738202
Research Article

p-Sulfonic Acid Calix[4]arene as an Efficient Catalyst for One-Pot Synthesis of Pharmaceutically Significant Coumarin Derivatives under Solvent-Free Condition

1Cellular and Molecular Biology Research Center (CMBRC), Health Research Institute, Babol University of Medical Sciences, Babol 47176 41367, Iran
2Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar 47416 95447, Iran

Received 12 October 2015; Accepted 26 November 2015

Academic Editor: Benedetto Natalini

Copyright © 2015 Hamed Tashakkorian 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. Sharma and V. J. Arya, “A review on fruits having anti-diabetic potential,” Journal of Chemical and Pharmaceutical Research, vol. 3, no. 2, pp. 204–212, 2011. View at Google Scholar · View at Scopus
  2. R. D. H. Murrey, D. Medez, and S. A. Brown, The Natural Coumarins Occurrences, Chemistry and Biochemistry, John Wiley Interscience, New York, NY, USA, 1982.
  3. K. M. Paramjeet, S. H. Dipak, and D. J. Arti, “Comparative study of microwave and conventional synthesis and pharmacological activity of coumarins: a review,” Journal of Chemical and Pharmaceutical Research, vol. 4, no. 1, pp. 822–850, 2012. View at Google Scholar
  4. L. A. Singer and N. P. Kong, “Vinyl radicals; Stereoselectivity in hydrogen atom transfer to equilibrated isomeric vinyl radicals,” Journal of American Chemical Society, vol. 88, no. 22, pp. 5213–5219, 1966. View at Publisher · View at Google Scholar
  5. B. G. Lake, “Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment,” Food and Chemical Toxicology, vol. 37, no. 4, pp. 423–453, 1999. View at Publisher · View at Google Scholar · View at Scopus
  6. H. M. Çakmak, S. Kahraman, F. Bayansal, and S. Çetinkaya, “A novel study on ZnO nanostructures: coumarin effect,” Philosophical Magazine Letters, vol. 92, no. 6, pp. 288–294, 2012. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Zahradnik, The Production and Application of Fluorescent Brightening Agents, John Wiley & Sons, New York, NY, USA, 1992.
  8. S. Weigt, N. Huebler, R. Strecker, T. Braunbeck, and T. H. Broschard, “Developmental effects of coumarin and the anticoagulant coumarin derivative warfarin on zebrafish (Danio rerio) embryos,” Reproductive Toxicology, vol. 33, no. 2, pp. 133–141, 2012. View at Publisher · View at Google Scholar · View at Scopus
  9. M. Çamur, M. Bulut, M. Kandaz, and O. Güney, “Effects of coumarin substituents on the photophysical properties of newly synthesised phthalocyanine derivatives,” Supramolecular Chemistry, vol. 21, no. 7, pp. 624–631, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. J. Chen, W. Liu, J. Ma et al., “Synthesis and properties of fluorescence dyes: tetracyclic pyrazolo [3,4-b] pyridine-based coumarin chromophores with intramolecular charge transfer character,” The Journal of Organic Chemistry, vol. 77, no. 7, pp. 3475–3482, 2012. View at Publisher · View at Google Scholar
  11. K. Rohini and P. S. Srikumar, “Therapeutic role of coumarins and coumarin-related compounds,” Journal of Thermodynamics & Catalysis, vol. 5, no. 2, article 130, 2014. View at Publisher · View at Google Scholar
  12. A. Lacy and R. O'Kennedy, “Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer,” Current Pharmaceutical Design, vol. 10, no. 30, pp. 3797–3811, 2004. View at Publisher · View at Google Scholar · View at Scopus
  13. X.-W. Yang, B. Xu, F.-X. Ran, R.-Q. Wang, J. Wu, and J.-R. Cui, “Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro,” Journal of Chinese Integrative Medicine, vol. 5, no. 1, pp. 56–60, 2007. View at Google Scholar · View at Scopus
  14. N. Hamdi, F. Bouabdallah, A. Romerosa, and R. Benhassen, “Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: a novel class of potential antibacterial and antioxidant agents,” Comptes Rendus Chimie, vol. 13, no. 10, pp. 1261–1268, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. A. A. H. Kadhum, A. A. Al-Amiery, A. Y. Musa, and A. B. Mohamad, “The antioxidant activity of new coumarin derivatives,” International Journal of Molecular Sciences, vol. 12, no. 9, pp. 5747–5761, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. G. Smitha, R. Sanjeeva, and G. Smitha, “ZrCl4catalyzed Pechmann reaction: synthesis of coumarins under solventfree conditions,” Synthetic Communications, vol. 34, no. 21, pp. 3997–4003, 2004. View at Google Scholar
  17. A. Kotali, I. S. Lafazanis, and P. A. Harris, “Synthesis of 6,7-diacylcoumarins via the transformation of a hydroxy into a carbonyl group,” Synthetic Communications, vol. 38, no. 22, pp. 3996–4006, 2008. View at Publisher · View at Google Scholar · View at Scopus
  18. I. P. Kostova, I. I. Manolov, I. N. Nicolova, and N. D. Danchev, “New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity,” II Farmaco, vol. 56, no. 9, pp. 707–713, 2001. View at Publisher · View at Google Scholar · View at Scopus
  19. R. O'Kennedy and R. D. Thornes, Coumarins: Biology, Applications and Mode of Action, John Wiley & Sons, Chichester, UK, 1997.
  20. Z. M. Nofal, M. I. El-Zahar, and S. S. Abd El-Karim, “Novel coumarin derivatives with expected biological activity,” Molecules, vol. 5, no. 2, pp. 99–113, 2000. View at Publisher · View at Google Scholar · View at Scopus
  21. S. S. Sahoo, S. Shukla, S. Nandy, and H. B. Sahoo, “Synthesis of novel coumarin derivatives and its biological evaluations,” European Journal of Experimental Biology, vol. 2, no. 4, pp. 899–908, 2012. View at Google Scholar
  22. W. H. Perkin, “XXIII.—On the hydride of aceto-salicyl,” Journal of Chemical Society, vol. 21, pp. 181–186, 1868. View at Google Scholar
  23. V. H. Pechmann and C. Duisberg, “Neue Bildungsweise der Cumarine. Synthese des Daphnetins,” Chemische Berichte, vol. 17, no. 1, pp. 929–936, 1884. View at Google Scholar
  24. G. Jones, “The Knoevenagel condensation,” in Organic Reactions, vol. 15, pp. 204–206, John Wiley & Sons, 1967. View at Publisher · View at Google Scholar
  25. G. Brufola, F. Fringuelli, O. Piermatti, and F. Pizzo, “Simple and efficient one-pot preparation of 3-substituted coumarins in water,” Heterocycles, vol. 43, no. 6, pp. 1257–1266, 1996. View at Publisher · View at Google Scholar · View at Scopus
  26. R. L. Shirner, “The reformatsky reaction,” Organic Reactions, vol. 1, pp. 15–18, 1942. View at Google Scholar
  27. D. N. Shah and N. M. Shah, “The Kostanecki-Robinson acylation of 5-hydroxy-6-acetyl-4-methylcoumarin,” Journal of the American Chemical Society, vol. 77, no. 6, pp. 1699–1700, 1955. View at Publisher · View at Google Scholar · View at Scopus
  28. N. S. Narasimhan, R. S. Mali, and M. V. Barve, “Synthetic application of lithiation peactions; part XIII. Synthesis of 3-phenylcoumarins and their benzo derivatives,” Synthesis, vol. 1979, no. 11, pp. 906–909, 1979. View at Publisher · View at Google Scholar
  29. I. Yavari, R. Hekmat-Shoar, and A. Zonouzi, “A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt,” Tetrahedron Letters, vol. 39, no. 16, pp. 2391–2392, 1998. View at Publisher · View at Google Scholar · View at Scopus
  30. F. N. Miros, G. Huang, Y. Zhao, N. Sakai, and S. Matile, “Coumarin synthesis on π-acidic surfaces,” Supramolecular Chemistry, vol. 27, no. 5-6, pp. 303–309, 2015. View at Publisher · View at Google Scholar · View at Scopus
  31. A. Rahmatpour and S. Mohammadian, “Polystyrene-supported TiCl4 as a novel, efficient and reusable polymeric Lewis acid catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions,” Comptes Rendus Chimie, vol. 16, no. 10, pp. 912–919, 2013. View at Publisher · View at Google Scholar · View at Scopus
  32. J. Albadi, F. Shirini, J. Abasi, N. Armand, and T. Motaharizadeh, “A green, efficient and recyclable poly (4-vinylpyridine)-supported copper iodide catalyst for the synthesis of coumarin derivatives under solvent-free conditions,” Comptes Rendus Chimie, vol. 16, no. 5, pp. 407–411, 2013. View at Publisher · View at Google Scholar · View at Scopus
  33. R. A. P. Castanheiro, A. M. S. Silva, N. A. N. Campos, M. S. J. Nascimento, and M. M. M. Pinto, “Antitumor activity of some prenylated xanthones,” Pharmaceuticals, vol. 2, no. 2, pp. 33–43, 2009. View at Publisher · View at Google Scholar · View at Scopus
  34. W. Yang and M. M. De Villiers, “The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes,” European Journal of Pharmaceutics and Biopharmaceutics, vol. 58, no. 3, pp. 629–636, 2004. View at Publisher · View at Google Scholar · View at Scopus
  35. W. Yang, D. P. Otto, W. Liebenberg, and M. M. de Villiers, “Effect of para-sulfonato-calix[n]arenes on the solubility, chemical stability, and bioavailability of a water insoluble drug nifedipine,” Current Drug Discovery Technologies, vol. 5, no. 2, pp. 129–139, 2008. View at Publisher · View at Google Scholar · View at Scopus
  36. W. Yang and M. M. de Villiers, “Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes,” Journal of Pharmacy and Pharmacology, vol. 56, no. 6, pp. 703–708, 2004. View at Publisher · View at Google Scholar · View at Scopus
  37. W. Yang and M. M. de Villiers, “Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic,” The AAPS Journal, vol. 7, no. 1, pp. E241–E248, 2005. View at Publisher · View at Google Scholar · View at Scopus
  38. J. G. Panchal, R. V. Patel, and S. K. Menon, “Preparation and physicochemical characterization of carbamazepine (CBMZ): para-sulfonated calix[n]arene inclusion complexes,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 67, no. 1-2, pp. 201–208, 2010. View at Publisher · View at Google Scholar · View at Scopus
  39. G.-S. Wang, H.-Y. Zhang, F. Ding, and Y. Liu, “Preparation and characterization of inclusion complexes of topotecan with sulfonatocalixarene,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 69, no. 1-2, pp. 85–89, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. M.-H. Paclet, C. F. Rousseau, C. Yannick, F. Morel, and A. W. Coleman, “An absence of non-specific immune response towards para-sulphonato-calix[n] arenes,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 55, no. 3-4, pp. 353–357, 2006. View at Publisher · View at Google Scholar · View at Scopus
  41. W. Yang, R. Manek, W. M. Kolling et al., “Physicochemical characterization of hydrated 4-sulphonato-calix [n] arenes: thermal, structural, and sorption properties,” Supramolecular Chemistry, vol. 17, no. 6, pp. 485–496, 2005. View at Google Scholar
  42. M. M. Lakouraj, M. Tajbakhsh, H. Tashakkorian, and K. Ghodrati, “Fast and efficient oxidation of sulfides to sulfones with N,N′-dibenzyl-N,N,N′,N′-tetramethyl diammonium permanganate,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 182, no. 2, pp. 485–490, 2007. View at Publisher · View at Google Scholar · View at Scopus
  43. M. M. Lakouraj, M. Tajbakhsh, and H. Tashakkorian, “Montmorillonite K10 catalyzed selective oxidation of sulfides to sulfoxides using hydrogen peroxide,” Letters in Organic Chemistry, vol. 4, no. 1, pp. 75–79, 2007. View at Publisher · View at Google Scholar · View at Scopus
  44. M. M. Lakouraj, M. Tajbakhsh, and H. Tashakkorian, “Ion exchange resin catalyzed selective oxidation of sulfides to sulfoxides using hydrogen peroxide,” Monatshefte für Chemie, vol. 138, no. 1, pp. 83–88, 2007. View at Publisher · View at Google Scholar · View at Scopus
  45. S. M. Baghbanian, N. Rezaei, and H. Tashakkorian, “Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media,” Green Chemistry, vol. 15, no. 12, pp. 3446–3458, 2013. View at Publisher · View at Google Scholar · View at Scopus
  46. R. L. Atkins and D. E. Bliss, “Substituted coumarins and azacoumarins. Synthesis and fluorescent properties,” Journal of Organic Chemistry, vol. 43, no. 10, pp. 1975–1980, 1978. View at Publisher · View at Google Scholar · View at Scopus
  47. A. S. R. Anjaeyulu, L. R. Row, C. S. Krishna, and C. Srinivasulu, “Synthesis of benzochromenes and related compounds I.5-6 and 7-8 benzochromanones and benzocoumarines,” Current Science, vol. 37, pp. 513–515, 1968. View at Google Scholar
  48. X. M. Dong, J.-F. Revol, and D. G. Gray, “Effect of microcrystallite preparation conditions on the formation of colloid crystals of cellulose,” Cellulose, vol. 5, no. 1, pp. 19–32, 1998. View at Publisher · View at Google Scholar · View at Scopus
  49. W. Keim, W. Korth, and P. Wasserscheid, WO 016, 902 (to BP Chemicals limited, UK, Akzo Nobel NV, Elementis UK Limited), chem. abstr. no. 132, 238691, 2000.
  50. J. Gui, X. Cong, D. Liu, X. Zhang, Z. Hu, and Z. Sun, “Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification,” Catalysis Communications, vol. 5, no. 9, pp. 473–477, 2004. View at Publisher · View at Google Scholar · View at Scopus
  51. C. D. Gutsche, Calixarenes Revisited, edited by J. F. Stoddart, The Royal Society of Chemistry, Cambridge, UK, 1998.
  52. S. Shinkai, K. Araki, T. Tsubaki, T. Some, and O. Manabe, “New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes,” Journal of the Chemical Society, Perkin Transactions 1, vol. 1, pp. 2297–2299, 1987. View at Publisher · View at Google Scholar
  53. S. A. Fernandes, R. Natalino, P. A. R. Gazolla, M. J. da Silva, and G. N. Jham, “p-Sulfonic acid calix[n]arenes as homogeneous and recyclable organocatalysts for esterification reactions,” Tetrahedron Letters, vol. 53, no. 13, pp. 1630–1633, 2012. View at Publisher · View at Google Scholar · View at Scopus
  54. R. Natalino, E. V. V. Varejão, M. J. da Silva, A. L. Cardoso, and S. A. Fernandes, “p-Sulfonic acid calix[n]arenes: the most active and water tolerant organocatalysts in esterification reactions,” Catalysis Science & Technology, vol. 4, no. 5, pp. 1369–1375, 2014. View at Publisher · View at Google Scholar · View at Scopus
  55. D. L. da Silva, S. A. Fernandes, A. A. Sabino, and Â. de Fátima, “p-Sulfonic acid calixarenes as efficient and reusable organocatalysts for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/-thiones,” Tetrahedron Letters, vol. 52, no. 48, pp. 6328–6330, 2011. View at Publisher · View at Google Scholar · View at Scopus
  56. S. Shimizu, N. Shimada, and Y. Sasaki, “Mannich-type reactions in water using anionic water-soluble calixarenes as recoverable and reusable catalysts,” Green Chemistry, vol. 8, no. 7, pp. 608–614, 2006. View at Publisher · View at Google Scholar · View at Scopus
  57. M. M. Lakouraj, H. Tashakkorian, and M. Rouhi, “One-pot synthesis of xanthones and dixanthones using calix [4] arene sulfonic acid under solvent free condition,” Chemical Science Transactions, vol. 2, no. 3, pp. 739–748, 2013. View at Publisher · View at Google Scholar
  58. S. M. Baghbanian, Y. Babajani, H. Tashakorian, S. Khaksar, and M. Farhang, “P-sulfonic acid calix[4]arene: an efficient reusable organocatalyst for the synthesis of bis(indolyl)methanes derivatives in water and under solvent-free conditions,” Comptes Rendus Chimie, vol. 16, no. 2, pp. 129–134, 2013. View at Publisher · View at Google Scholar · View at Scopus