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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1723–1731 | Cite as

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

  • A. Bari
  • S. S. Ali
  • A. Kadi
  • I. A. Hashmi
  • S. W. Ng
Article

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.

Keywords

3-formylchromone pyranopyrones antimicrobial activity enzyme inhibitors Knoevenagel–Cope reaction pharmacophore urease inhibitory 

Notes

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.

References

  1. 1.
    G. Sabitha, Aldrichimica Acta, 29, 15 (1996).Google Scholar
  2. 2.
    M. Kawasei, T. Tanaka, H. Kan, S. Tani, H. Nakashima, and H. Sakagami, In Vivo, 21, 829 (2007).Google Scholar
  3. 3.
    L. Jund, J. Corse, A. S. King, H. Bayne, and K. Mihrag, Phytochemistry, 10, 2971 (1971).CrossRefGoogle Scholar
  4. 4.
    S. L. El-Ansary, E. I. Aly, and M. A. Halem, J. Pharm. Sci., 33, 379 (1992).Google Scholar
  5. 5.
    Y. D. Reddy and V. V. Somayojulu, J. Ind. Chem. Soc., 58, 599 (1981).Google Scholar
  6. 6.
    N. Modranka, J. Nawrot, and E. Graczyk, Eur. J. Med. Chem., 41, 1301 (2006).CrossRefGoogle Scholar
  7. 7.
    O. A. Abd Allah, Farmaco, 55, 641 (2000).CrossRefGoogle Scholar
  8. 8.
    S. S. Parmar and R. Kumar, J. Med. Chem., 11, 635 (1968).CrossRefGoogle Scholar
  9. 9.
    D. A. Horton, G. T. Bourne, and M. L. Smythe, Chem Rev., 103, 893 (2003).CrossRefGoogle Scholar
  10. 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).Google Scholar
  11. 11.
    B. Wang, Z. Y. Yang, and T. Li, Bioorg. Med. Chem., 14, 6012 (2006).CrossRefGoogle Scholar
  12. 12.
    B. H. Havsteen, Flavonoids, 96, 67 (2002).Google Scholar
  13. 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).CrossRefGoogle Scholar
  14. 14.
    M. M. Dutta, B. N. Goswani, and J. C. S. Kataky, J. Heterocycl. Chem., 23 , 793 (1986).CrossRefGoogle Scholar
  15. 15.
    S. C. Sharma, Bull. Chem. Soc. Jpn., 40, 2422 (1967).CrossRefGoogle Scholar
  16. 16.
    P. Foltinova, M. Lacova, and D. Loos, Farmaco, 55, 21 (2000).CrossRefGoogle Scholar
  17. 17.
    V. N. Chaubey and H. Singh, Bull. Chem. Soc. Jpn., 43, 2233 (1970).CrossRefGoogle Scholar
  18. 18.
    W. O. Foye and P. Tovivich, J. Pharm. Sci., 66, 1607 (1977).CrossRefGoogle Scholar
  19. 19.
    E. B. Akerblom, J. Med. Chem., 17, 609 (1974).CrossRefGoogle Scholar
  20. 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).CrossRefGoogle Scholar
  21. 21.
    N. Karali, A. Gursoy, N. Terzioglu, S. Ozkirimli, H. Ozer, and A. C. Ekinci, Arch. Pharm., 331, 254 (1998).CrossRefGoogle Scholar
  22. 22.
    U. Albrecht, M. Lalk, and P. Langer, Bioorg. Med. Chem., 13, 1531 (2005).CrossRefGoogle Scholar
  23. 23.
    E. T. Oganesyan, V. A. Tuskayev, and L. S. Sarkisov, Khim. Farm. Zh., 28, No. 12, 17 (1994).Google Scholar
  24. 24.
    A. Khodairy, J. Chin. Chem. Soc., 54, 93 (2007).Google Scholar
  25. 25.
    A. Nohara, H. Kuriki, T. Saijo, K. Ukawa, T. Murata, M. Kanno, and Y. Sanno, J. Med. Chem., 18 , 34 (1975).CrossRefGoogle Scholar
  26. 26.
    R. Gašparová and M. Lácová, Molecules, 10, 937 (2005).CrossRefGoogle Scholar
  27. 27.
    A. Nohara, T. Umetani, and Y. Sanno, Tetrahedron Lett., 22, 1995 (1973).CrossRefGoogle Scholar
  28. 28.
    R. Sagar, P. Singh, R. Kumar, P. R. Maulikb, and A. K. Shaw, Carbohydr. Res., 340, 1287 (2005).CrossRefGoogle Scholar
  29. 29.
    C. K. Ghosh, A. Ray, and A. Patra, J. Heterocycl. Chem., 38, 1459 (2001).CrossRefGoogle Scholar
  30. 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).CrossRefGoogle Scholar
  31. 31.
    G. N. Rolinson and Elizabeth J. Russell, Antimicrob. Agents Chemother., 2, 51, (1972).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • A. Bari
    • 1
    • 2
  • S. S. Ali
    • 2
  • A. Kadi
    • 1
  • I. A. Hashmi
    • 3
  • S. W. Ng
    • 4
  1. 1.Department of Pharmaceutical Chemistry, College of PharmacyKing Saud UniversityRiyadhSaudi Arabia
  2. 2.Research Center, College of PharmacyKing Saud UniversityRiyadhSaudi Arabia
  3. 3.Department of ChemistryUniversity of KarachiKarachiPakistan
  4. 4.Department of ChemistryUniversity of MalayaKuala LumpurMalaysia

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