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Articles

Vol. 1 No. 2 (2010): April– June 2010

Synthesis and Pharmacological Evaluation of a Series of 3-[(E)-3-(substituted aryl) acryloyl]-2H-chromen-2-one as Anti-inflammatory, Analgesic and Antioxidant Agents

DOI
https://doi.org/10.37285/ijddd.1.2.5
Submitted
November 24, 2024
Published
2010-05-15

Abstract

A new series of 3-[(E)-3-(substituted aryl)acryloyl]-2H-chromen-2-one (2a-k) were synthesized by Claisen-Schmidt condensation of 3-acetyl coumarin (1) and substituted aromatic aldehyde in presence of piperidine and glacial acetic acid. Structures of all new synthesized compounds were characterized by spectral data (UV, IR, and 1H NMR). The titled compounds were screened for in vivo anti-inflammatory and analgesic activities at a dose 200 mg/kg b.w. and in vitro antioxidant activity. Among the series, compounds 2c and k exhibited significant anti-inflammatory activity in model of acute inflammation such as carrageenan-induced rat edema paw and were compared with diclofenac (13.5 mg/kg b.w.) as standard drug. These compounds were also found to have significant analgesic activity in acetic acid induced writhing model and antipyretic activity in yeast-induced pyrexia model along with minimum ulcerogenic index. Compounds 2e and k exhibited moderate antioxidant activity in 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical scavenging method as compared to ascorbic acid and butylated hydroxyl toluene as standard drug.

References

  1. [1] Silverstein, F.E.; Faish, G.; Goldstein, J.L.; Simon,L.S.Am. Med. Assn. 2000, 284, 1247.
  2. [2] Unangst, P.C.; Conner, D.F.; Celenco, W.A.; Sorensen, R.J.; Kostlan, C.A.; Sircar, J.C. J. Med. Chem. 1994, 37, 322.
  3. [3] Habeeb, G.A.; Rao, P.N.; Knanus, E.E. J. Med. Chem. 2001, 44, 3039.
  4. [4] Maddi, V.S.; Raghu, K.S.; Rao M.N.A. J. Pharm. Sci. 1992, 81, 964.
  5. [5] Khode, S.; Maddi, V.; Aragade, P.; Palkar, M. Eur. J. Med. Chem. 2009, 44, 1682.
  6. [6] Maddi, V.; Mamledesai, S.N.; Satyanarayana, D.; Swamy, S. Indian. J. Pharm. Sci. 2007, 69(6), 847.
  7. [7] Kalgutkar,A.S. Expert Opin. Investig. Drugs, 1999, Vol. 9, pp 831–835.
  8. [8] Tally, J.J.; Bertenshaw, R.S.; Brown, D.L.; Carter, J.S. J. Med. Chem. 2000, 43, 1661.
  9. [9] Dogne, J.M.; Supuran, C.T.; Pratico, D. J. Med. Chem. 2005, 48, 2251.
  10. [10] Kontogiorgis, C.A.; Hadjipavlou-Litina, D.J. Bioorg. Med. Chem. Lett. 2004, 14, 611.
  11. [11] Paya, M.; Goodwin, P.A.; Hoult, J.R. Biochem. Pharmacol. 1994, 48(3), 445.
  12. [12] Komatsu, W.; Ishihara, K.; Murata, M.; Saito, H.; Shinohara, K. Free. Rad. Biol. Med. 2003, 34(8), 1006.
  13. [13] Harborne, J.B. The Flavonoids, Advances in Research, Chapman & Hall, New York NY.1988, pp 329-388.
  14. [14] Karali, N.; Kocabalkanli, A.; Gursoy, A.; Ates, O. Il. Farmaco. 2002, 57, 589.
  15. [15] OECD/ OCDC, OECD ‘Guidelines for testing of chemicals’ Revised draft Guidelines 423: Acute oral toxicity- Acute toxic class method, revised document, October 2000.
  16. [16] Winter, C.A.; Risley, E.A.; Nuss, G.W. Proc. Soc. Exp. Biol. Med. 1962, 111, 544.
  17. [17] Koster, R.; Anderson, M.; De Beer, E.J. Fed. Proc. 1959, 18, 412.
  18. [18] Loux, J.J.; DePalma, P.D.; Yankell, S.L. Toxicol. Appl. Pharma. 1972, 22, 672.
  19. [19] H.G. Vogel (Ed.), Drug Discovery and Evaluation: Pharmacological Assays, third ed. Springer-Verlag, Berlin, Heidelberg, 2002.
  20. [20] Sreejayan, N.; Rao, M.N.A. Int. J. Pharma. 1993, 100, 93.
  21. [21] Alich, A.A.; Welsh, V.J.; Wittmess, L.E. J. Pharm. Sci. 1983, 72, 1457.

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