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Synthesis of Some New Heterocyclic Compounds Derived from 3-Formylchromones and Their Antimicrobial Evaluation

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Chemistry of Heterocyclic Compounds Aims and scope

The synthesis and antimicrobial evaluation of a series of chromone-linked substituted heterocyclic derivatives is described. The condensation of 3-formylchromone with acetoacetamide under Knoevenagel–Cope reaction conditions was also explored, and the condensation with 4-hydroxy-6-methyl-2H-pyran-2-one constitutes a facile route to pyranopyrone fused systems. Most of the compounds exhibit good antimicrobial properties.

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References

  1. G. Sabitha, Aldrichimica Acta, 29, 15 (1996).

    Google Scholar 

  2. M. Kawasei, T. Tanaka, H. Kan, S. Tani, H. Nakashima, and H. Sakagami, In Vivo, 21, 829 (2007).

    Google Scholar 

  3. L. Jund, J. Corse, A. S. King, H. Bayne, and K. Mihrag, Phytochemistry, 10, 2971 (1971).

    Article  Google Scholar 

  4. S. L. El-Ansary, E. I. Aly, and M. A. Halem, J. Pharm. Sci., 33, 379 (1992).

    CAS  Google Scholar 

  5. Y. D. Reddy and V. V. Somayojulu, J. Ind. Chem. Soc., 58, 599 (1981).

    CAS  Google Scholar 

  6. N. Modranka, J. Nawrot, and E. Graczyk, Eur. J. Med. Chem., 41, 1301 (2006).

    Article  Google Scholar 

  7. O. A. Abd Allah, Farmaco, 55, 641 (2000).

    Article  CAS  Google Scholar 

  8. S. S. Parmar and R. Kumar, J. Med. Chem., 11, 635 (1968).

    Article  CAS  Google Scholar 

  9. D. A. Horton, G. T. Bourne, and M. L. Smythe, Chem Rev., 103, 893 (2003).

    Article  CAS  Google Scholar 

  10. K. Nakano, T. Nakayachi, E. Yasumoto, S. R. Morshed, K. Hashimoto, H. Kikuchi, H. Nishikawa, K. Sugiyama, O. Amano, M. Kawase, and H. Sakagami, Anticancer Res., 24, 711 (2004).

    CAS  Google Scholar 

  11. B. Wang, Z. Y. Yang, and T. Li, Bioorg. Med. Chem., 14, 6012 (2006).

    Article  CAS  Google Scholar 

  12. B. H. Havsteen, Flavonoids, 96, 67 (2002).

    CAS  Google Scholar 

  13. L. Pisco, M. Kordian, K. Peseke, H. Feist, D. Michalik, E. Estrada, J. Carvalho, G. Hamilton, D. Rando, and J. Quincoces, Eur. J. Med. Chem., 41, 401 (2006).

    Article  CAS  Google Scholar 

  14. M. M. Dutta, B. N. Goswani, and J. C. S. Kataky, J. Heterocycl. Chem., 23 , 793 (1986).

    Article  CAS  Google Scholar 

  15. S. C. Sharma, Bull. Chem. Soc. Jpn., 40, 2422 (1967).

    Article  CAS  Google Scholar 

  16. P. Foltinova, M. Lacova, and D. Loos, Farmaco, 55, 21 (2000).

    Article  CAS  Google Scholar 

  17. V. N. Chaubey and H. Singh, Bull. Chem. Soc. Jpn., 43, 2233 (1970).

    Article  Google Scholar 

  18. W. O. Foye and P. Tovivich, J. Pharm. Sci., 66, 1607 (1977).

    Article  CAS  Google Scholar 

  19. E. B. Akerblom, J. Med. Chem., 17, 609 (1974).

    Article  CAS  Google Scholar 

  20. D. Miller, S. Wang, J. Reid, W. Xie, B. Gauvin, M. Kelley, J. Sarup, D. G. Sawutz, M. Miski, R. E. Dolle, and C. R. Faltynek, Drug Dev. Res., 34, 344 (1995).

    Article  CAS  Google Scholar 

  21. N. Karali, A. Gursoy, N. Terzioglu, S. Ozkirimli, H. Ozer, and A. C. Ekinci, Arch. Pharm., 331, 254 (1998).

    Article  CAS  Google Scholar 

  22. U. Albrecht, M. Lalk, and P. Langer, Bioorg. Med. Chem., 13, 1531 (2005).

    Article  CAS  Google Scholar 

  23. E. T. Oganesyan, V. A. Tuskayev, and L. S. Sarkisov, Khim. Farm. Zh., 28, No. 12, 17 (1994).

    CAS  Google Scholar 

  24. A. Khodairy, J. Chin. Chem. Soc., 54, 93 (2007).

    CAS  Google Scholar 

  25. A. Nohara, H. Kuriki, T. Saijo, K. Ukawa, T. Murata, M. Kanno, and Y. Sanno, J. Med. Chem., 18 , 34 (1975).

    Article  CAS  Google Scholar 

  26. R. Gašparová and M. Lácová, Molecules, 10, 937 (2005).

    Article  Google Scholar 

  27. A. Nohara, T. Umetani, and Y. Sanno, Tetrahedron Lett., 22, 1995 (1973).

    Article  Google Scholar 

  28. R. Sagar, P. Singh, R. Kumar, P. R. Maulikb, and A. K. Shaw, Carbohydr. Res., 340, 1287 (2005).

    Article  CAS  Google Scholar 

  29. C. K. Ghosh, A. Ray, and A. Patra, J. Heterocycl. Chem., 38, 1459 (2001).

    Article  CAS  Google Scholar 

  30. J. W. Lockman, M. D. Reeder, R. Robinson, P. A. Ormonde, D. M. Cimbora, B. L. Williams, and J. A. Willardsen, Bioorg. Med. Chem. Lett., 21, 1724 (2011).

    Article  CAS  Google Scholar 

  31. G. N. Rolinson and Elizabeth J. Russell, Antimicrob. Agents Chemother., 2, 51, (1972).

    Article  CAS  Google Scholar 

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We thank the Research Center, College of Pharmacy and Deanship of Scientific Research, King Saud University for supporting this study. S. W. Ng thanks the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for financial support.

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Correspondence to A. Bari.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1860-1869, December, 2013.

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Bari, A., Ali, S.S., Kadi, A. et al. Synthesis of Some New Heterocyclic Compounds Derived from 3-Formylchromones and Their Antimicrobial Evaluation. Chem Heterocycl Comp 49, 1723–1731 (2014). https://doi.org/10.1007/s10593-014-1424-4

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  • DOI: https://doi.org/10.1007/s10593-014-1424-4

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