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Synthesis, Characterization and Antibacterial Study of 7-O-Substituted Derivatives of Chlorinated Coumarin
Corresponding Author(s) : Aziz-ur Rehman
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
In this research work, a series of 7-O-alkyl/aralkyl/acyl substituted derivatives of chlorinated coumarin was synthesized and screened for their antibacterial activity. The parent compound 6-chloro-7-hydroxy-4-methyl-2H-chromen-2-one (3) was prepared by the coupling of homogeneous mixing of 4-chlororesorcinol (1) and ethylacetoacetate (2) in a conc. H2SO4 medium. Further, the 7-O-substituted derivatives of coumarins 5a-i and 7a-h were prepared by the reaction of parent compound with different alkyl/aralkyl/acyl halides 4a-i and 6a-h. The synthesized compounds were supported via spectral data. The prepared compounds were evaluated for inhibition activity against bacterial strains including Gram-positive and Gram-negative and were observed that some of the compounds exhibited activity to varying degree.
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- A. Behrami and I. Krasniqi, Res. J. Pharm. Biol. Chem. Sci., 3, 369 (2012).
- A.A. Al-Rifai, M.T. Ayoub, A.K. Shakya, K.A. Abu Safieh and M.S. Mubarak, Med. Chem. Res., 21, 468 (2012); doi:10.1007/s00044-011-9553-0.
- N.N. Farshori, M.R. Banday, A. Ahmad, A.U. Khan and A. Rauf, Med. Chem. Res., 20, 535 (2011); doi:10.1007/s00044-010-9347-9.
- Y. Shi and C.H. Zhou, Bioorg. Med. Chem. Lett., 21, 956 (2011); doi:10.1016/j.bmcl.2010.12.059.
- S.M. Naik and H.B. Naik, Asian J. Chem., 11, 1540 (1999).
- K.N. Venugopala and B.S. Jayashree, Asian J. Chem., 16, 407 (2004).
- O. Alam, S.K. Gupta, M. Imran and S.A. Khan, Asian J. Chem., 17, 1281 (2005).
- K.N. Venugopala, B.S. Jayashree and M. Attimarad, Asian J. Chem., 16, 872 (2004).
- P. Desai, A.C. Champaneri and K.R. Desai, Asian J. Chem., 12, 1327 (2000).
- Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, K.M. Khan, M. Asraf and I. Afzal, Asian J. Phram. Biol. Res., 2, 100 (2012).
- M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); doi:10.2174/157018009787158481.
- C.-R. Yang, Y. Zhang, M.R. Jacob, S.I. Khan, Y.-J. Zhang and X.-C. Li, Antimicrob. Agents Chemother., 50, 1710 (2006); doi:10.1128/AAC.50.5.1710-1714.2006.
References
A. Behrami and I. Krasniqi, Res. J. Pharm. Biol. Chem. Sci., 3, 369 (2012).
A.A. Al-Rifai, M.T. Ayoub, A.K. Shakya, K.A. Abu Safieh and M.S. Mubarak, Med. Chem. Res., 21, 468 (2012); doi:10.1007/s00044-011-9553-0.
N.N. Farshori, M.R. Banday, A. Ahmad, A.U. Khan and A. Rauf, Med. Chem. Res., 20, 535 (2011); doi:10.1007/s00044-010-9347-9.
Y. Shi and C.H. Zhou, Bioorg. Med. Chem. Lett., 21, 956 (2011); doi:10.1016/j.bmcl.2010.12.059.
S.M. Naik and H.B. Naik, Asian J. Chem., 11, 1540 (1999).
K.N. Venugopala and B.S. Jayashree, Asian J. Chem., 16, 407 (2004).
O. Alam, S.K. Gupta, M. Imran and S.A. Khan, Asian J. Chem., 17, 1281 (2005).
K.N. Venugopala, B.S. Jayashree and M. Attimarad, Asian J. Chem., 16, 872 (2004).
P. Desai, A.C. Champaneri and K.R. Desai, Asian J. Chem., 12, 1327 (2000).
Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, K.M. Khan, M. Asraf and I. Afzal, Asian J. Phram. Biol. Res., 2, 100 (2012).
M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); doi:10.2174/157018009787158481.
C.-R. Yang, Y. Zhang, M.R. Jacob, S.I. Khan, Y.-J. Zhang and X.-C. Li, Antimicrob. Agents Chemother., 50, 1710 (2006); doi:10.1128/AAC.50.5.1710-1714.2006.