Synthesis of Chrysin Analogs with a Heteroaryl Group and Evaluation for their Anti-inflammatory Activities

헤테로 고리를 갖는 크리신 유도체의 합성 및 항염증 작용에 대한 평가

  • Received : 2011.09.28
  • Accepted : 2011.11.18
  • Published : 2011.12.31

Abstract

Chrysin analogs with 2-heteroaryl groups were synthesized and evaluated for their inhibitory activities against $PGE_2$ and NO production from LPS-induced RAW 264.7 cells. Chrysin analogs were synthesized from 2-hydroxy-4,6-dimethoxy-acetophenone and heteroaryl aldehydes in 3 steps. The tested chrysin analogs showed decreased inhibitory activity against $PGE_2$ and NO production than those of chrysin.

Keywords

References

  1. Hecker, M., Preiss, C., Klemm, P. and Brusse, R. : Inhibition by antioxidants of nitric oxide synthase expression in murine macrophages: role of nuclear factor kappa B and interferon regulatory factor 1. Br. J. Pharmacol. 118, 2178 (1996). https://doi.org/10.1111/j.1476-5381.1996.tb15660.x
  2. Pearce, F. L., Befus, A. D. and Bienenstock, J. : Mucosal mast cells. III. Effect of quercetin and other flavonoids on antigeninduced histamine secretion from rat intestinal mast cells. J. Allergy Clin. Immunol. 73, 819 (1984). https://doi.org/10.1016/0091-6749(84)90453-6
  3. Fishkin, R. J. and Winslow, J. T. : Endotoxin-induced reduction of social investigation by mice: interation with amphetamine and anti-inflammatory drugs. Psychopharmacol. 132, 335 (1997). https://doi.org/10.1007/s002130050353
  4. Habtemariam, S. : Flavonoids as inhibitors or enhancers of the cytotoxicity of tumor necrosis factor-a in L-929 tumor cells. J. Nat. Prod. 60, 775 (1997). https://doi.org/10.1021/np960581z
  5. Liang, Y.-C., Tsai, S. H., Tsai, D. C., Lin-Shiau, S. Y. and Lin, J. K. : Supression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferatoractivated receptor-$\gamma$ by flavonoids in mouse macrophages. FEBS Lett. 496, 12 (2001). https://doi.org/10.1016/S0014-5793(01)02393-6
  6. Park, H., Dao, T. T. and Kim, H. P. : Synthesis and inhibition of PGE2 production of 6,8-disubstituted chrysin derivatives. European J. Med. Chem. 40, 943 (2005). https://doi.org/10.1016/j.ejmech.2005.04.013
  7. Gurung, S. K., Kim, H. P. and Park, H. : Inhibition of Prostaglandin $E_{2}$ production by synthetic wogonin analogs. Arch. Pharm. Res. 32, 1503 (2009). https://doi.org/10.1007/s12272-009-2101-5
  8. Gurung, S. K., Kim, H. P. and Park, H. : Structural alteration of wogonin significantly reduce the inhibitory activity against COX-2 catalyzed $PGE_{2}$ production from LPS-induced RAW 264.7 cells. Biomolecules & Therapeutics 17, 418 (2009). https://doi.org/10.4062/biomolther.2009.17.4.418
  9. Che, H., Lim, H., Kim, H. P. and Park, H. : A chrysin analog exhibited strong inhibitory activities against both $PGE_{2}$ and NO production. Eur. J. Med. Chem. 46, 4657 (2011). https://doi.org/10.1016/j.ejmech.2011.04.044
  10. Dao, T. T., Kim, S. B., Sin, K.-S., Kim, S., Kim, H. P. and Park, H. : Synthesis and biological activities of 8-arylflavones. Arch. Pharm. Res. 27, 278 (2004). https://doi.org/10.1007/BF02980059
  11. Chi, Y. S., Lim, H., Park, H. and Kim, H. P. : Effects of wogonin, a plant flavone from Scutellaria radix, on the suppression of cyclooxygenase-2 and the induction of inducible nitric oxide synthase in LPS-treated RAW 264.7 cells. Biochem. Pharmacol. 61, 1195 (2001). https://doi.org/10.1016/S0006-2952(01)00597-4