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