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International Journal of Medicinal Chemistry
Volume 2013, Article ID 984329, 7 pages
http://dx.doi.org/10.1155/2013/984329
Research Article

Synthesis and In Vitro Cytotoxic Activity of Chromenopyridones

1Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar 143005, India
2Botanical and Environmental Sciences, Guru Nanak Dev University, Amritsar 143005, India

Received 19 October 2012; Revised 27 November 2012; Accepted 11 December 2012

Academic Editor: Giulio Rastelli

Copyright © 2013 Balwinder Singh 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. S. Dadiboyena and A. Nefzi, “Synthesis of functionalized tetrasubstituted pyrazolyl heterocycles—a review,” European Journal of Medicinal Chemistry, vol. 46, no. 11, pp. 5258–5275, 2011. View at Publisher · View at Google Scholar
  2. W. Du, “Towards new anticancer drugs: a decade of advances in synthesis of camptothecins and related alkaloids,” Tetrahedron, vol. 59, no. 44, pp. 8649–8687, 2003. View at Publisher · View at Google Scholar · View at Scopus
  3. G. Valdameri, E. G. Bastide, B. Peres et al., “Substituted chromones as highly potent nontoxic inhibitors, specific for the breast cancer resistance protein,” Journal of Medicinal Chemistry, vol. 55, no. 2, pp. 966–970, 2012. View at Publisher · View at Google Scholar
  4. A. Gaspar, T. Silva, M. Yáñez et al., “Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors,” Journal of Medicinal Chemistry, vol. 54, no. 14, pp. 5165–5173, 2011. View at Publisher · View at Google Scholar · View at Scopus
  5. F. A. Ramos, Y. Takaishi, M. Shirotori et al., “Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion (Allium cepa) skin,” Journal of Agricultural and Food Chemistry, vol. 54, no. 10, pp. 3551–3557, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. R. Goel, V. Sharma, A. Budhiraja, and M. P. S. Ishar, “Synthesis and evaluation of novel 3a, 9a-dihydro-1-ethoxycarbonyl-1-cyclopenteno[5, 4-b]benzopyran-4-ones as antifungal agents,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 14, pp. 4665–4667, 2012. View at Publisher · View at Google Scholar
  7. M. Kuroda, S. Uchida, K. Watanabe, and Y. Mimaki, “Chromones from the tubers of Eranthis cilicica and their antioxidant activity,” Phytochemistry, vol. 70, no. 2, pp. 288–293, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. R. I. Brinkworth, M. J. Stoermer, and D. P. Fairlie, “Flavones are inhibitors of HIV-1 proteinase,” Biochemical and Biophysical Research Communications, vol. 188, no. 2, pp. 631–637, 1992. View at Publisher · View at Google Scholar · View at Scopus
  9. I. W. Setnikar, M. J. Murmann, M. J. Magistrett, P. da Re, and L. Verlicchi, “N-substituted 8-aminomethylchromones, a new class of central nervous system stimulants,” Journal of medicinal and pharmaceutical chemistry, vol. 3, pp. 471–488, 1961. View at Google Scholar · View at Scopus
  10. S. A. Galal, A. S. Abd El-All, M. M. Abdallah, and H. I. El-Diwani, “Synthesis of potent antitumor and antiviral benzofuran derivatives,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 9, pp. 2420–2428, 2009. View at Publisher · View at Google Scholar · View at Scopus
  11. K. Serge, G. T. Hubert, B. Janine, B. Pierre, and M. Marie, “Synthesis and evaluate the anti-allergic and antihistamine activity of benzyl-3-chromones (homo-isoflavones),” European Journal of Medicinal Chemistry, vol. 24, no. 5, pp. 541–546, 1989. View at Publisher · View at Google Scholar
  12. T. H. Tseng, S. K. Chuang, C. C. Hu et al., “The synthesis of morusin as a potent antitumor agent,” Tetrahedron, vol. 66, no. 6, pp. 1335–1340, 2010. View at Publisher · View at Google Scholar · View at Scopus
  13. T. Raj, R. K. Bhatia, A. kapur, M. Sharma, A. K. Saxena, and M. P. S. Ishar, “Cytotoxic activity of 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4H-chromene-3-carbothioic acid N-phenylamides,” European Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 790–794, 2010. View at Publisher · View at Google Scholar · View at Scopus
  14. M. P. S. Ishar, G. Singh, S. Singh, K. K. Sreenivasan, and G. Singh, “Design, synthesis, and evaluation of novel 6-chloro-/fluorochromone derivatives as potential topoisomerase inhibitor anticancer agents,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 5, pp. 1366–1370, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. Q. Li, A. Claiborne, T. Li et al., “Design, synthesis, and activity of 4-quinolone and pyridone compounds as nonthiol-containing farnesyltransferase inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 21, pp. 5367–5370, 2004. View at Publisher · View at Google Scholar · View at Scopus
  16. H. M. Hassanin and S. M. El-edfawy, “Novel heterocyclic derivatives of 2-quinolinone associated with antibacterial and antitumor potencies,” Hetreocycles, vol. 85, no. 10, pp. 2421–2436, 2012. View at Publisher · View at Google Scholar
  17. D. D. Erol and N. Yulug, “Synthesis and antimicrobial investigation of thiazolinoalkyl-4(1H)-pyridones,” European Journal of Medicinal Chemistry, vol. 29, no. 11, pp. 893–897, 1994. View at Publisher · View at Google Scholar · View at Scopus
  18. A. G. E. Amr and M. M. Abdulla, “Anti-inflammatory profile of some synthesized heterocyclic pyridone and pyridine derivatives fused with steroidal structure,” Bioorganic and Medicinal Chemistry, vol. 14, no. 13, pp. 4341–4352, 2006. View at Publisher · View at Google Scholar · View at Scopus
  19. X. Fan, D. Feng, Y. Qu et al., “Practical and efficient synthesis of pyrano[3,2-c]pyridone, pyrano[4,3-b]pyran and their hybrids with nucleoside as potential antiviral and antileishmanial agents,” Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 3, pp. 809–813, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. M. E. Wall, M. C. Wani, C. E. Cook, K. H. Palmer, A. T. McPhail, and G. A. Sim, “Plant antitumor agents VI: the isolation and structure of taxol, a novel antilekemic and antitumor agent from Taxus brevifolia,” Journal of American Chemical Society, vol. 88, no. 16, pp. 3888–3892, 1966. View at Publisher · View at Google Scholar
  21. W. D. Kingsbury, J. C. Boehm, D. R. Jakas et al., “Synthesis of water-soluble (aminoalkyl)camptothecin analogues: inhibition of topoisomerase I and antitumor activity,” Journal of Medicinal Chemistry, vol. 34, no. 1, pp. 98–107, 1991. View at Google Scholar · View at Scopus
  22. M. S. Butler, “Natural products to drugs: natural product-derived compounds in clinical trials,” Natural Product Reports, vol. 25, no. 3, pp. 475–516, 2008. View at Publisher · View at Google Scholar · View at Scopus
  23. G. Singh, R. Singh, N. K. Girdhar, and M. P. S. Ishar, “A versatile route to 2-alkyl-/aryl-amino-3-formyl- and hetero-annelated-chromones, through a facile nucleophilic substitution at C2 in 2-(N-methylanilino)-3-formylchromones,” Tetrahedron, vol. 58, no. 12, pp. 2471–2480, 2002. View at Publisher · View at Google Scholar · View at Scopus
  24. G. Singh, G. Singh, and M. P. S. Ishar, “Pericyclic transformations at the periphery of chromen-4-one (4H-1-benzopyran-4-one): an unusual preference for a 1,5-shift of allylic moieties over the ene reaction,” Helvetica Chimica Acta, vol. 86, no. 1, pp. 169–180, 2003. View at Publisher · View at Google Scholar · View at Scopus
  25. D. Mou, W. Zhao, T. Zhang et al., “Two new chromanone derivatives from the roots and stems of Nicotiana tabacum and their cytotoxicity,” Heterocycles, vol. 85, no. 10, pp. 2485–2490, 2012. View at Publisher · View at Google Scholar
  26. P. Skehan, R. Storeng, D. Scudiero et al., “New colorimetric cytotoxicity assay for anticancer-drug screening,” Journal of the National Cancer Institute, vol. 82, no. 13, pp. 1107–1112, 1990. View at Google Scholar · View at Scopus
  27. W. Ren, Z. Qiao, H. Wang, L. Zhu, and L. Zhang, “Flavonoids: promising anticancer agents,” Medicinal Research Reviews, vol. 23, no. 4, pp. 519–534, 2003. View at Publisher · View at Google Scholar · View at Scopus
  28. A. M. Senderowicz, “The cell cycle as a target for cancer therapy: basic and clinical findings with the small molecule inhibitors flavopiridol and UCN-01,” Oncologist, vol. 7, supplement 3, pp. 12–19, 2002. View at Google Scholar · View at Scopus
  29. M. R. Vijayababu, P. Kanagaraj, A. Arunkumar, R. Ilangovan, M. M. Aruldhas, and J. Arunakaran, “Quercetin-induced growth inhibition and cell death in prostatic carcinoma cells (PC-3) are associated with increase in p21 and hypophosphorylated retinoblastoma proteins expression,” Journal of Cancer Research and Clinical Oncology, vol. 131, no. 11, pp. 765–771, 2005. View at Publisher · View at Google Scholar · View at Scopus
  30. S. M. Kupchan, D. R. Streelman, and A. T. Sneden, “Psorospermin, a new antileukemic xanthone from psorospermum febrifugum,” Journal of Natural Products, vol. 43, no. 2, pp. 296–301, 1980. View at Google Scholar · View at Scopus
  31. J. M. Cassady, W. M. Baird, and C. J. Chang, “Natural products as a source of potential cancer chemotherapeutic and chemopreventive agents,” Journal of Natural Products, vol. 53, no. 1, pp. 23–41, 1990. View at Publisher · View at Google Scholar · View at Scopus
  32. M. Hansen, S. J. Lee, J. M. Cassady, and L. H. Hurley, “Molecular details of the structure of a psorospermin—DNA covalent/intercalation complex and associated DNA sequence selectivity,” Journal of the American Chemical Society, vol. 118, no. 24, pp. 5553–5561, 1996. View at Publisher · View at Google Scholar · View at Scopus