Synthesis of Anti-inflammatory 2'-Hydroxychalcone Derivatives

항염증효과를 갖는 2'-하이드록시찰콘 유도체의 합성

  • Lee, Young-Sook (College of Pharmacy, Institute of Pharmaceutical Research and Development, Wonkwang University) ;
  • Kim, Hak-Sung (College of Pharmacy, Institute of Pharmaceutical Research and Development, Wonkwang University)
  • 이영숙 (원광대학교 약학대학 약품연구소) ;
  • 김학성 (원광대학교 약학대학 약품연구소)
  • Received : 2011.09.19
  • Accepted : 2011.09.21
  • Published : 2011.10.31

Abstract

It was reported that the potency of TMMC derivatives was related to the presence of the 2'-hydroxy group on the A ring. Also, 4-dimethylamino group on the B ring lowered the anti-inflammatory potency of the chalcones. We synthesized various derivatives of 2'-hydroxy chalcones having other substituents on B ring. The synthetic derivatives showed the more potent anti-inflammatory effect, comparable to that of the TMMC derivatives reported previously.

Keywords

References

  1. Callister, C. A., Le Bail, J. C., Trouilas, P., Pouget, C., Habrioux, G., Chulia, A. J. and Duroux, J. L. : Chalcones: Structural requirements for antioxidant, estrogenic and antiproliferative activities. Anticancer Res. 21, 3949 (2001).
  2. Anto, R. J., Sukumara, K., Kuttan, G., Rao, M. N., Subbaraju, V. and Kuttan, R. : Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett. 97, 33 (1995). https://doi.org/10.1016/0304-3835(95)03945-S
  3. De Vincenzo, R., Ferlini, C., Distefano, M., Gaggini, C., Riva, A., Bombardelli, E., Morazzoni, P., Valenti, P., Belluti, F., Ranelletti, F. O., Mancuso, S. and Scambia, G. : In vitro evaluation of newly developed chalcone analogues in human cancer cells. Cancer Chemother. Pharmacol. 46, 305 (2000).
  4. Edwards, M. L., Stemerick, D. M. and Sunkara, P. S. : Chalcones: A new class of antimitotic agents. J. Med. Chem. 33, 1948 (1990). https://doi.org/10.1021/jm00169a021
  5. Ko, H. H., Tsao, L. T., Yu, K. L., Liu, C. T., Wang, J. P. and Lin, C. N. : Structure-activity relationship studies on chalcone derivatives-the potent inhibition of chemical mediators release. J. Med. Chem. 46, 2813 (2003). https://doi.org/10.1021/jm030213+
  6. Nam, N.-H., Kim, Y., You, Y.-J., Hong, D.-H., Kim, H.-M. and Ahn, B.-Z. : Cytotoxic 2',5'-dihydroxychalcones with unexpected antiangiogenic activity. Eur. J. Med. Chem. 38, 179 (2003) https://doi.org/10.1016/S0223-5234(02)01443-5
  7. Rojas, J., Dominguez, J. N., Charris, J. E., Lobo, G., Pay, M. and Ferrndiz, M. L. : Synthesis and inhibitory activity of dimethylamino-chalcone derivatives on the induction of nitric oxide synthase. Eur. J. Med. Chem. 37, 699 (2002). https://doi.org/10.1016/j.ejmech.2004.09.006
  8. Won, S. J., Liu, C.T., Tsao, L. T., Weng, J. R., Ko, H. H., Wang, J. P. and Lin, C. N. : Synthetic chalcones as potential antiinflammatory and cancer chemopreventive agents. Eur. J. Med. Chem. 40, 103 (2005). https://doi.org/10.1016/j.ejmech.2004.09.006
  9. Sabzevari, O., Galati, G., Moridani, M. Y., Siraki, A. and O'Brien, P. J. : Molecular cytotoxic mechanisms of anticancer hydroxychalcones. Chem. Biol. Interact. 148, 57 (2004). https://doi.org/10.1016/j.cbi.2004.04.004
  10. Jin, F., Jin, X. Y., Jin, Y. L., Sohn, D. W., Kim, S.-A., Sohn, D. H., Kim, Y. C. and Kim, H. S. : Structural requirements of 2',4',6'- tris(methoxymethoxy)chalcone derivatives for anti-inflammatory activity: The importance of a 2'-hydroxy moiety. Arch. Pharm. Res. 30, 1359 (2007). https://doi.org/10.1007/BF02977357
  11. Lee, S. H., Seo, G. S., Kim, H. S., Woo, S. W., Ko, G. and Sohn, D. H. : 2',4',6'-Tri(methoxymethoxy)chalcone attenuates hepatic stellate cell proliferation by a heme oxygenasedependent pathway. Biochem. Pharmacol. 72, 1322 (2006). https://doi.org/10.1016/j.bcp.2006.08.004
  12. Lee, S. H., Seo, G. S., Kim, J. Y., Jin, X. Y., Kim, H. D. and Sohn, D. H. : Heme oxygenase-1 mediates anti-inflammatory effects of 2',4',6'-tris(methoxymethoxy) chalcone. Eur. J. Pharmacol. 532, 178 (2006). https://doi.org/10.1016/j.ejphar.2006.01.005
  13. Jin, F., Jin, X. Y., Jin, Y. L., Sohn, D. W., Kim, S.-A., Sohn, D. H., Kim, Y. C. and Kim, H. S. : Structural requirements of 2',4',6'- tris(methoxymethoxy)chalcone derivatives for anti-inflammatory activity: The importance of a 2'-hydroxy moiety. Arch. Pharm. Res. 30, 1359 (2007). https://doi.org/10.1007/BF02977357
  14. Jin, Y. L., Jin, X. Y., Jin, F., Sohn, D. H. and Kim, H. S. : Structure activity relationship studies of anti-inflammatory TMMC derivatives: 4-dimethylamino group on the B ring responsible for lowering the potency. Arch. Pharm. Res. 31, 1145 (2008). https://doi.org/10.1007/s12272-001-1281-7