Table of Contents Author Guidelines Submit a Manuscript
Advances in Pharmacological Sciences
Volume 2015, Article ID 527159, 9 pages
http://dx.doi.org/10.1155/2015/527159
Research Article

BF3·Et2O Catalysed 4-Aryl-3-phenyl-benzopyrones, Pro-SERMs, and Their Characterization

Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India

Received 19 May 2015; Accepted 22 July 2015

Academic Editor: Todd C. Skaar

Copyright © 2015 Ambika Srivastava 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. L. J. Black, C. D. Jones, and J. F. Falcone, “Antagonism of estrogen action with a new benzothiophene derived antiestrogen,” Life Sciences, vol. 32, no. 9, pp. 1031–1036, 1983. View at Publisher · View at Google Scholar · View at Scopus
  2. A. U. Buzdar, C. Marcus, F. Holmes, V. Hug, and G. Hortobagyi, “Phase II evaluation of LY156758 in metastatic breast cancer,” Oncology, vol. 45, no. 5, pp. 344–345, 1988. View at Publisher · View at Google Scholar · View at Scopus
  3. K. R. Snyder, N. Sparano, and J. M. Malinowski, “Raloxifene hydrochloride,” American Journal of Health-System Pharmacy, vol. 57, no. 18, pp. 1669–1678, 2000. View at Google Scholar · View at Scopus
  4. V. C. Jordan, E. Phelps, and J. U. Lindgren, “Effects of anti-estrogens on bone in castrated and intact female rats,” Breast Cancer Research and Treatment, vol. 10, no. 1, pp. 31–35, 1987. View at Publisher · View at Google Scholar · View at Scopus
  5. L. J. Black, M. Sato, E. R. Rowley et al., “Raloxifene (LY139481 HCI) prevents bone loss and reduces serum cholesterol without causing uterine hypertrophy in ovariectomized rats,” The Journal of Clinical Investigation, vol. 93, no. 1, pp. 63–69, 1994. View at Publisher · View at Google Scholar
  6. M. M. Gottardis and V. C. Jordan, “Antitumor actions of keoxifene and tamoxifen in the N-nitrosomethylurea-induced rat mammary carcinoma model,” Cancer Research, vol. 47, no. 15, pp. 4020–4024, 1987. View at Google Scholar · View at Scopus
  7. M. A. Anzano, C. W. Peer, J. M. Smith et al., “Chemoprevention of mammary carcinogenesis in the rat: combined use of raloxifene and 9-cis-retinoic acid,” Journal of the National Cancer Institute, vol. 88, no. 2, pp. 123–125, 1996. View at Publisher · View at Google Scholar · View at Scopus
  8. B. Ettinger, D. M. Black, B. H. Mitlak et al., “Reduction of vertebral fracture risk in postmenopausal women with osteoporosis treated with raloxifene: results from a 3-year randomized clinical trial,” The Journal of the American Medical Association, vol. 282, no. 7, pp. 637–645, 1999. View at Publisher · View at Google Scholar · View at Scopus
  9. S. R. Cummings, S. Eckert, K. A. Krueger et al., “The effect of raloxifene on risk of breast cancer in postmenopausal women: results from the MORE randomized trial,” The Journal of the American Medical Association, vol. 281, no. 23, pp. 2189–2197, 1999. View at Publisher · View at Google Scholar · View at Scopus
  10. M. Clarke, R. Collins, C. Davies, J. Godwin, R. Gray, and R. Peto, “The EBCTCG secretariat, clinical trial service, unit, radcliffe infirmary, Oxford OX2 6HE, UK,” The Lancet, vol. 351, pp. 1451–1467, 1998. View at Google Scholar
  11. B. Fisher, J. P. Costantino, D. L. Wickerham et al., “Tamoxifen for prevention of breast cancer: report of the National Surgical Adjuvant Breast and Bowel Project P-1 Study,” Journal of the National Cancer Institute, vol. 90, no. 18, pp. 1371–1388, 1998. View at Publisher · View at Google Scholar · View at Scopus
  12. R. R. Love, R. B. Mazess, H. S. Barden et al., “Effects of tamoxifen on bone mineral density in postmenopausal women with breast cancer,” The New England Journal of Medicine, vol. 326, no. 13, pp. 852–856, 1992. View at Publisher · View at Google Scholar · View at Scopus
  13. V. J. Assikis, P. Neven, V. C. Jordan, and I. Vergote, “A realistic clinical perspective of tamoxifen and endometrial carcinogenesis,” European Journal of Cancer A, vol. 32, no. 9, pp. 1464–1476, 1996. View at Publisher · View at Google Scholar · View at Scopus
  14. E. J. Lederer, “Chemistry and biochemistry of some mammalian secretions and excretions,” Journal of the Chemical Society, pp. 2115–2125, 1949. View at Publisher · View at Google Scholar
  15. G. G. Freeman, “Isolation of alternariol and alternariol monomethyl ether from Alternaria dauci (kühn) groves and skolko,” Phytochemistry, vol. 5, no. 4, pp. 719–725, 1966. View at Publisher · View at Google Scholar · View at Scopus
  16. W. T. L. Sidwell, H. Fritz, and C. Tamm, “Autumnariol und Autumnariniol, zwei neue Dibenzo-α-pyrone aus Eucomis autumnalis Graeb. Nachweis einer Fernkopplung über sechs Bindungen in den magnetischen Protonenresonanz—Spektren,” Helvetica Chimica Acta, vol. 54, no. 1, pp. 207–215, 1971. View at Publisher · View at Google Scholar
  17. L. Farkas, F. Soti, M. Incze, and M. Nogradi, “Synthese natürlicher Dibenzo-α-pyrone, I. Synthese des Autumnariniols und des Autumnariniols,” Chemische Berichte, vol. 107, no. 12, pp. 3874–3877, 1974. View at Publisher · View at Google Scholar
  18. S. Ghosal, J. P. Reddy, and V. K. Lal, “Shilajit I: chemical constituents,” Journal of Pharmaceutical Sciences, vol. 65, no. 5, pp. 772–773, 1976. View at Publisher · View at Google Scholar · View at Scopus
  19. B. Naser-Hijazi, B. Stolze, and K. S. Zanker, Second Proceedings of the International Society of the Coumarin Investigators, Springer, Berlin, Germany, 1994.
  20. R. D. H. Murray, J. Méndez, and S. A. Brown, The Natural Coumarin: Occurrence, Chemistry and Biochemistry, John Wiley, Chichester, UK, 1982.
  21. J. D. Hepworth, C. D. Gabbutt, and B. N. Heron, Comprehensive Heterocyclic Chemistry II, vol. 5, Pergamon Press, Oxford, UK, 1996.
  22. F. M. Deans, Naturally Occurring Oxygen Ring Compounds, Butterworths, London, UK, 1963.
  23. J. A. Joule and K. Mills, Eds., Heterocyclic Chemistry, Blackwell Science, Oxford, UK, 4th edition, 2006.
  24. R. D. H. Murray, “Naturally occurring plant coumarins,” Fortschritte der Chemie Organischer Naturstoffe, vol. 35, pp. 199–249, 1978. View at Google Scholar
  25. G. R. Geen, J. M. Evans, and A. K. Vong, in Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Eds., vol. 5, p. 469, Pergamon Press, Oxford, UK, 1984.
  26. H.-X. Xu and S. F. Lee, “Activity of plant flavonoids against antibiotic-resistant bacteria,” Phytotherapy Research, vol. 15, no. 1, pp. 39–43, 2001. View at Google Scholar
  27. J. M. Hamilton-Miller, “Antimicrobial properties of tea (Camellia sinensis L.),” Antimicrobial Agents and Chemotherapy, vol. 39, no. 11, pp. 2375–2377, 1995. View at Publisher · View at Google Scholar
  28. K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, and D. N. Nicolaides, “Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities,” Current Pharmaceutical Design, vol. 10, no. 30, pp. 3813–3833, 2004. View at Publisher · View at Google Scholar · View at Scopus
  29. J. R. Hwu, R. Singha, S. C. Hong et al., “Synthesis of new benzimidazole-coumarin conjugates as anti-hepatitis C virus agents,” Antiviral Research, vol. 77, no. 2, pp. 157–162, 2008. View at Publisher · View at Google Scholar · View at Scopus
  30. S. Sardari, Y. Mori, K. Horita, R. G. Micetich, S. Nishibe, and M. Daneshtalab, “Synthesis and antifungal activity of coumarins and angular furanocoumarins,” Bioorganic & Medicinal Chemistry, vol. 7, no. 9, pp. 1933–1940, 1999. View at Publisher · View at Google Scholar · View at Scopus
  31. D. Egan, P. James, D. Cooke, and R. O'Kennedy, “Studies on the cytostatic and cytotoxic effects and mode of action of 8-nitro-7-hydroxycoumarin,” Cancer Letters, vol. 118, no. 2, pp. 201–211, 1997. View at Publisher · View at Google Scholar · View at Scopus
  32. P. Valenti, A. Rampa, M. Recanatini et al., “Synthesis, cytotoxicity and SAR of simple geiparvarin analogues,” Anti-Cancer Drug Design, vol. 12, no. 6, pp. 443–451, 1997. View at Google Scholar · View at Scopus
  33. C. Spino, M. Dodier, and S. Sotheeswaran, “Anti-HIV coumarins from calophyllum seed oil,” Bioorganic and Medicinal Chemistry Letters, vol. 8, no. 24, pp. 3475–3478, 1998. View at Publisher · View at Google Scholar · View at Scopus
  34. L. M. Bedoya, M. Beltran, R. Sancho et al., “4-Phenylcoumarins as HIV transcription inhibitors,” Bioorganic & Medicinal Chemistry Letters, vol. 15, no. 20, pp. 4447–4450, 2005. View at Publisher · View at Google Scholar
  35. K.-H. Lee, “Current developments in the discovery and design of new drug candidates from plant natural product leads,” Journal of Natural Products, vol. 67, no. 2, pp. 273–283, 2004. View at Publisher · View at Google Scholar
  36. D. Yu, M. Suzuki, L. Xie, S. L. Morris-Natschke, and K.-H. Lee, “Recent progress in the development of coumarin derivatives as potent anti-HIV agents,” Medicinal Research Reviews, vol. 23, no. 3, pp. 322–345, 2003. View at Publisher · View at Google Scholar · View at Scopus
  37. S. Kirkiacharian, D. T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire, “Structure–activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors,” Farmaco, vol. 57, no. 9, pp. 703–708, 2002. View at Publisher · View at Google Scholar · View at Scopus
  38. A. G. Kidane, H. Salacinski, A. Tiwari, K. R. Bruckdorfer, and A. M. Seifalian, “Anticoagulant and antiplatelet agents: their clinical and device application(s) together with usages to engineer surfaces,” Biomacromolecules, vol. 5, no. 3, pp. 798–813, 2004. View at Publisher · View at Google Scholar · View at Scopus
  39. K. M. Khan, Z. S. Saify, M. Z. Khan et al., “Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 19, no. 4, pp. 373–379, 2004. View at Publisher · View at Google Scholar · View at Scopus
  40. G. Appendino, E. Mercalli, N. Fuzzati et al., “Antimycobacterial coumarins from the Sardinian giant fennel (Ferula communis),” Journal of Natural Products, vol. 67, no. 12, pp. 2108–2110, 2004. View at Publisher · View at Google Scholar · View at Scopus
  41. N. Hamdi, M. Saoud, and A. Romerosa, “4-Hydroxy coumarine: a versatile reagent for the synthesis of heterocyclic and vanillin ether coumarins with biological activities,” in Bioactive Heterocycles V, vol. 11 of Topics in Heterocyclic Chemistry, pp. 283–301, Springer, Berlin, Germany, 2007. View at Publisher · View at Google Scholar
  42. F. Chimenti, B. Bizzarri, A. Bolasco et al., “Synthesis and in vitro selective anti-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides,” European Journal of Medicinal Chemistry, vol. 41, no. 2, pp. 208–212, 2006. View at Publisher · View at Google Scholar · View at Scopus
  43. C. Ito, M. Itoigawa, Y. Mishina et al., “Chemical constituents of Calophyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins,” Journal of Natural Products, vol. 66, no. 3, pp. 368–371, 2003. View at Publisher · View at Google Scholar · View at Scopus
  44. I. Kostova, “Synthetic and natural coumarins as cytotoxic agents,” Current Medicinal Chemistry—Anti-Cancer Agents, vol. 5, no. 1, pp. 29–46, 2005. View at Publisher · View at Google Scholar · View at Scopus
  45. G. Melagraki, A. Afantitis, O. Igglessi-Markopoulou et al., “Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts,” European Journal of Medicinal Chemistry, vol. 44, no. 7, pp. 3020–3026, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. C. A. Kontogiorgis and D. J. Hadjipavlou-Litina, “Synthesis and antiinflammatory activity of coumarin derivatives,” Journal of Medicinal Chemistry, vol. 48, no. 20, pp. 6400–6408, 2005. View at Publisher · View at Google Scholar · View at Scopus
  47. S. Stanchev, V. Hadjimitova, T. Traykov, T. Boyanov, and I. Manolov, “Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 7, pp. 3077–3082, 2009. View at Publisher · View at Google Scholar · View at Scopus
  48. C. A. Kontogiorgis and D. J. Hadjipavlou-Litina, “Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage,” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 3, pp. 611–614, 2004. View at Publisher · View at Google Scholar · View at Scopus
  49. C. Xiao, Z.-G. Song, and Z.-Q. Liu, “Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA,” European Journal of Medicinal Chemistry, vol. 45, no. 6, pp. 2559–2566, 2010. View at Publisher · View at Google Scholar
  50. O. M. Abdel Hafez, K. M. Amin, N. A. Abdel-Latif, T. K. Mohamed, E. Y. Ahmed, and T. Maher, “Synthesis and antitumor activity of some new xanthotoxin derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 7, pp. 2967–2974, 2009. View at Publisher · View at Google Scholar · View at Scopus
  51. V. Reutrakul, P. Leewanich, P. Tuchinda et al., “Cytotoxic coumarins from Mammea harmandii,” Planta Medica, vol. 69, no. 11, pp. 1048–1051, 2003. View at Publisher · View at Google Scholar · View at Scopus
  52. I. Kempen, D. Papapostolou, N. Thierry et al., “3-Bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo,” British Journal of Cancer, vol. 88, no. 7, pp. 1111–1118, 2003. View at Publisher · View at Google Scholar · View at Scopus
  53. P. O'Kennedy and R. D. Thornes, Eds., Coumarins: Biology, Applications and Mode of Action, John Wiley & Sons, Chichester, UK, 1997.
  54. L. Zhi, C. M. Tegley, E. A. Kallel et al., “5-Aryl-1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal human progesterone receptor agonists,” Journal of Medicinal Chemistry, vol. 41, no. 3, pp. 291–302, 1998. View at Publisher · View at Google Scholar · View at Scopus
  55. J. M. Schmidt, G. B. Tremblay, M. Pagé et al., “Synthesis and evaluation of a novel nonsteroidal-specific endothelial cell proliferation inhibitor,” Journal of Medicinal Chemistry, vol. 46, no. 8, pp. 1289–1292, 2003. View at Publisher · View at Google Scholar · View at Scopus
  56. K. Hajela, K. Kapoor, and R. Kapil, “Synthesis and post-coital contraceptive activity of ether and ester analogues of 2,3-diaryl-2H-1-benzopyrans,” Bioorganic & Medicinal Chemistry, vol. 3, pp. 1417–1420, 1995. View at Google Scholar
  57. K. Hajela and R. S. Kapil, “Synthesis and post-coital contraceptive activity of a new series of substituted 2,3-diaryl-2H-1-benzopyrans,” European Journal of Medicinal Chemistry, vol. 32, no. 2, pp. 135–139, 1997. View at Publisher · View at Google Scholar
  58. K. Hajela, J. Pandey, A. Dwivedy et al., “Resolution, molecular structure and biological activities of the D- and L-enantiomers of potent anti-implantation agent, DL-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran,” Bioorganic & Medicinal Chemistry, vol. 7, no. 9, pp. 2083–2090, 1999. View at Publisher · View at Google Scholar · View at Scopus
  59. H. Pechmann and C. Duisberg, “Neue Bildungsweise der Cumarine. Synthese des Daphnetins. I,” Chemische Berichte, vol. 17, no. 1, pp. 929–936, 1884. View at Publisher · View at Google Scholar
  60. J. Johnson, “The Perkin reaction and related reactions,” Organic Reactions, vol. 1, pp. 210–265, 1942. View at Google Scholar
  61. G. Jones, “The Knoevenagel condensation,” Organic Reactions, vol. 15, pp. 204–599, 1967. View at Google Scholar
  62. 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
  63. R. L. Shriner, “The reformatsky reaction,” in Organic Reactions, vol. 1, pp. 1–58, John Wiley & Sons, 1942. View at Publisher · View at Google Scholar
  64. 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
  65. J. R. Johnson, “Perkin reaction and related reactions,” Organic Reactions, vol. 1, p. 210, 1942. View at Google Scholar
  66. M. H. Elnagdi, S. O. Abdallah, K. M. Ghoneim, E. M. Ebied, and K. N. Kassab, “Synthesis of some Coumarin derivatives as potential LaserDyes,” Journal of Chemical Research, Synopses, no. 2, pp. 44–45, 1997. View at Publisher · View at Google Scholar