Skip to main navigation menu Skip to main content Skip to site footer
##common.pageHeaderLogo.altText##

Articles

Vol. 2 No. 2 (2011): April – June 2011

Acetylcholinesterase/butylcholinesterase Inhibitory Activities of Substituted Chromenone Derivatives

DOI
https://doi.org/10.37285/ijddd.2.2.1
Submitted
November 28, 2024
Published
2024-12-08

Abstract

3,6-Disubstituted-2H-2-chromenones 3a-l and 3,4,6-trisubstituted 2H-2-chromenones 3m & 3n were synthesized from 5-bromosalicylaldehyde 1 and 5-bromo-2-hydroxyacetophenone 5. Suzuki coupling of 5-bromosalicylaldehyde with various phenylboronic acids yielded 5-substituted salicylaldehydes 2b-l and these compounds were reacted with various β-ketoesters in presence of piperidine afforded substituted chromenone derivatives 3a-l in very good yields. The compounds 3m & 3n were prepared by Suzuki coupling of 2m. Synthesized compounds 3a-n were screened for in vitro AChE & BuChE activities and found that the compound 3n shown significant activity where as 3g, 3h, 3j, 3k & 3m compounds were shown moderate activity of AChE. The compound 3d shown potent activity, where as 3c & 3m shown moderate activity of BuChE and the results were compared with the standard drug Galanthamine.

References

  1. [1] (a) O’Kennedy, R.; Thomas, R. D. Coumarins:Biology, Applications, and Mode of Action; Eds.; Wiley: Chichester, UK, 1997; (b) Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins; Wiley: New York, 1982.
  2. [2] Maxwell, A. Mol Microbiol. 1993, 9, 681.
  3. [3] Musicki, B.; Periers, A. M.; Laurin, P.; Ferroud, D.; Benedetti, Y.; Lachaud, S.; Chatreaux, F.; Haesslein, J. L.; Iltis, A.; Pierre, C.; Khider, J.; Tessot, N.; Airault, M.; Demassey, J.; Dupuis-Hamelin, C.; Lassaigne, P.; Bonnefoy, A.; Vicat, P.; Klich, M. Bioorg. Med. Chem. Lett. 2000, 10, 1695.
  4. [4] Chimichi, S.; Boccalini, M.; Cosimelli, B.; Viola, G.; Vedaldi, D.; Dall’Acqua, F. Tetrahedron. Lett. 2002, 43, 7473.
  5. [5] Yoakim, C.; Bonneau, P. R.; De´ziel, R.; Doyon, L.; Duan, J.; Guse, I.; Landry, S.; Malenfant, E.; Naud, J.; Ogilvie, W. W.; O’Meara, J. A.; Plante, R.; Simoneau, B.; Thavonekham, B.; Bo¨s, M.; Cordingley, M. G. Bioorg. Med. Chem. Lett. 2004, 14, 739.
  6. [6] Uchiumi, F.; Hatano, T.; Ito, H.; Yoshida, T.; Tanuma, S. Antiviral Res. 2003, 58, 89.
  7. [7] Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S. L.; Lee, K. H. Med. Res. Rev. 2003, 23, 322.
  8. [8] Jeddy, A. S.; Gleason, B. L. Ann. Pharmacother. 2003, 37, 1502.
  9. [9] Pineo, G.; Hull, R. D. Hematol. Oncol. Clin. North Am. 2003, 17, 201.
  10. [10] (a) Guiotto, A.; Chilin, A.; Manzini, P.; Dall’Acqua,F.; Bordin, F.; Rodighiero, P. Farmaco. 1995, 50, 479; (b) Rollinger, J. M.; Hornick, A.; Langer, T.; Stuppner,H.; Prast, H. J. Med. Chem. 2004, 47, 6248.
  11. [11] (a) Hariprassad, V.; Talele, T. T.; Kulkarni, V. M.Pharm. Pharmacol. Commun. 1998, 4, 365;(b) Kaye, P. T.; Musa, M. A.; Nichinda, A. T.;Nocanda, X. W. Synth. Commun. 2004, 34, 2575.
  12. [12] Refouvelet, B.; Guyon, C.; Jacquot, Y.; Girard, C.; Fein, H.; Be´valot, F.; Robert, J-F.; Heyd, B.; Mantion, G.; Richert, L.; Xicluna, A. Eur. J. Med. Chem. 2004, 39, 931.
  13. [13] Sharma, V. K.; Saharo, P. D.; Sharma, N.; Rastogi, R. C.; Ghoshal, S. K.; Mohan, D. Spectrochim. Acta A. 2003, 59, 1161.
  14. [14] (a) Gangadasu, B.; Janaki Ram Reddy, M.; Ravinder,M.; Bharath Kumar, S.; China Raju, B.; Pranay Kumar, K.; Murthy, U. S. N. Jayathirtha Rao, V. Eur. J. Med. Chem. 2009, 44, 4661; (b) Gangdasu, B.; China Raju, B.; Jayathirtha Rao, V.J. Heterocycl. Chem. 2009, 46, 1213; (c) Narender, P.; Ravinder, M.; Partha Sarathi Sadhu, China Raju, B.; Ramesh, Ch. Jayathirtha Rao, V. Helv. Chim. Acta. 2009, 92, 959; (d) Ashok Kumar, J.; Tiwari, A. K. Ali, A. Z.; Madhusudana, K.; Srinivasa Reddy, B.; Ramakrishna, S.; China Raju, B. J Enz Inhib Med Chem. 2010, 25, 80.
  15. [15] China Raju, B.; Tiwari, A. K.; Ashok Kumar, J.; Ali, A. Z.; Agawane, S. B.; Saidachary, G.; Madhusudana, K. Bioorg. Med. Chem. 2010, 18, 358.
  16. [16] (a) Subba Rao, N. V.; Sundara Murthy, V. Proc. Indian Acad. Sci. 1961, 54, 105;(b) Subba Rao, N. V.; Sundara Murthy, V. Chem.Abstr. 1962, Vol 56, pp 5920a.
  17. [17] Ellman, G. L.; Courtney, K. D.; Andres Jr, V. V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88.
  18. [18] Bradford, M. M. Anal. Biochem. 1976, 72, 248.
  19. [19] SMART & SAINT; Software Reference manuals. Versions 6.28a & 5.625, Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, U.S.A., 2001.
  20. [20] Sheldrick, G. M. Acta Cryst. A. 2008, 64, 112.

Similar Articles

1 2 3 4 5 6 > >> 

You may also start an advanced similarity search for this article.