DOI QR코드

DOI QR Code

Synthesis of Biologically Active Chalcones and their Anti-inflammatory Effects

  • Jeon, Jae-Ho (Institute of Natural Medicine, Hallym University) ;
  • Kim, Si-Jun (Department of Chemistry and Institute of Applied Chemistry, Hallym University) ;
  • Kim, Cheol-Gi (Department of Chemistry and Institute of Applied Chemistry, Hallym University) ;
  • Kim, Jin-Kyung (Department of Biomedical Science, College of Natural Science, Catholic University of Daegu) ;
  • Jun, Jong-Gab (Institute of Natural Medicine, Hallym University)
  • Received : 2011.12.06
  • Accepted : 2012.01.07
  • Published : 2012.03.20

Abstract

Chalcones have been reported to have various biological activities including antitumor, antiparasitic, antileishmanial, antioxidative, superoxide scavenging, antibacterial, and PTP1B activity. Due to the limited natural resources, we had to prepare sizable quantities of biologically active chalcones for bio-tests. Therefore, Claisen-Schmidt condensation between substituted acetophenones and corresponding aldehydes enabled us to prepare chalcones for inflammatory studies. Chalcones thus prepared showed significant suppression of nitric oxide (NO) production at $10{\mu}M$.

Keywords

References

  1. Cushine, T. P. T.; Lamb, A. J. Int. J. Antimicrob. Ag. 2005, 26, 343. https://doi.org/10.1016/j.ijantimicag.2005.09.002
  2. Shibata, S. Stem Cells 1994, 12, 44. https://doi.org/10.1002/stem.5530120109
  3. Liu, X. L.; Xu, Y. J.; Go, M. L. Eur. J. Med. Chem. 2008, 43, 1681. https://doi.org/10.1016/j.ejmech.2007.10.007
  4. Kwon, H. S.; Park, J. H.; Kim, D. H.; Kim, Y. H.; Park, J. H.; Shin, H. K.; Kim, J. K. J. Mol. Med. (Berl) 2008, 86, 1287. https://doi.org/10.1007/s00109-008-0395-2
  5. Liu, M.; Wilarirat, P.; Go, M.-L. J. Med. Chem. 2001, 44, 4443. https://doi.org/10.1021/jm0101747
  6. Nagai, H.; He, J.-X.; Tani, T.; Akao, T. J. Pharm. Pharmacol. 2007, 59, 1421. https://doi.org/10.1211/jpp.59.10.0013
  7. Jeon, J.-H.; Kim, M. R.; Jun, J.-G. Synthesis 2011, 370.
  8. Nielsen, S. F.; Christensen, S. B.; Cruciani, G.; Kharazmi, A.; Liljefors, T. J. Med. Chem. 1998, 41, 4819. https://doi.org/10.1021/jm980410m
  9. Chen, M.; Christensen, S. B.; Zhai, L.; Rasmussen, M. H.; Theander, T. G.; Frokjaer, S.; Steffansen, S.; Davidsen, J.; Khrazmi, A. J. Infec. Dis. 1997, 176, 1327. https://doi.org/10.1086/514129
  10. Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem. Int. Ed. 2000, 39, 734. https://doi.org/10.1002/(SICI)1521-3773(20000218)39:4<734::AID-ANIE734>3.0.CO;2-I
  11. Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939. https://doi.org/10.1021/ja002033k
  12. Lee, Y. R.; Wang, X.; Xia, L. Molecules 2007, 12, 1420. https://doi.org/10.3390/12071420
  13. Claisen, L.; Claparede, A. Ber. 1881, 14, 2460. https://doi.org/10.1002/cber.188101402192
  14. Scmidt, J. G. Ber. 1881, 14, 1459. https://doi.org/10.1002/cber.188101401306
  15. Vermooy, J. H.; Dentener, M. A.; Suylen, R. J. van.; Buurman, W. A.; Wouters, E. F. Am. J. Respir Cell Mol. Biol. 2002, 26,152. https://doi.org/10.1165/ajrcmb.26.1.4652
  16. Nabaei-Bidhendi, G.; Bannerjee, N. R. J. Ind. Chem. Soc. 1990, 67, 43.
  17. Ruffin, B.; Castellan, A.; Grelier, S.; Nourmamode, A.; Riela, S.; Trichet, V. J. Appl. Poly. Sci. 1998, 69, 2517. https://doi.org/10.1002/(SICI)1097-4628(19980926)69:13<2517::AID-APP1>3.0.CO;2-D
  18. Kharazmi, A.; Christensen, S. B.; Ming, C.; Theander, T. G. US 5,985,935, 1999.
  19. Claisen, L.; Eisleb, O. Justus Liebigs Ann. Chem. 1913, 401, 21. https://doi.org/10.1002/jlac.19134010103

Cited by

  1. Synthesis of 4-(2-Amino)ethoxy-3′,4′-dihydroxychalcones and Their Antioxidant and Cytotoxic Effects on Human Tumor Cells vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10253
  2. Naturally occurring chalcones and their biological activities vol.15, pp.1, 2016, https://doi.org/10.1007/s11101-014-9387-8
  3. Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology pp.1336-9075, 2017, https://doi.org/10.1007/s11696-017-0316-3
  4. Simple Syntheses of Two New Benzo-Fused Macrocycles Incorporating Chalcone Moiety vol.2014, pp.None, 2014, https://doi.org/10.1155/2014/485014
  5. Synthesis and characterization of new 3,5-disubstituted-4,5-dihydro-1H-pyrazole and their carbothioamide derivatives vol.6, pp.1, 2012, https://doi.org/10.5155/eurjchem.6.1.78-83.1148
  6. In vitro and in vivo anticancer studies of 2'-hydroxy chalcone derivatives exhibit apoptosis in colon cancer cells by HDAC inhibition and cell cycle arrest vol.16, pp.None, 2017, https://doi.org/10.17179/excli2016-643