DOI QR코드

DOI QR Code

고리형 알콕시기를 함유한 크리신 유도체의 합성 및 일산화질소 생성 억제작용

Synthesis of 8-Cycloalkoxychrysin Analogs and their Inhibitory Activity Against NO Production

  • Kim, Sung-Soo (School of Medicine, Kangwon National University) ;
  • Park, Haeil (College of Pharmacy, Kangwon National University)
  • 투고 : 2015.01.23
  • 심사 : 2015.02.13
  • 발행 : 2015.02.28

초록

Several 8-cycloalkoxychrysin analogs were synthesized from 6-benzyloxy-5,8-dihydroxyflavone and cycloalkanols in 2 steps and we evaluated their inhibitory activities against NO production from LPS-induced RAW 264.7 cells. Among tested analogs, two analogs with cyclopentyl substructure (796 and 798) showed strong inhibitory activity against NO production.

키워드

참고문헌

  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-g by flavonoids in mouse macrophages. FEBS Lett. 496, 12 (2001). https://doi.org/10.1016/S0014-5793(01)02393-6
  6. Dao, T. T., Oh, J. W., Chi, Y. S., Kim, H. P., Sin, K.-S. and Park, H. : Synthesis and PGE2 inhibitory activities of vinylated and allylated chrysin analogues. Arch. Pharm. Res. 26, 581 (2003). https://doi.org/10.1007/BF02976703
  7. 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
  8. Park, H., Dao, T. T. and Kim, H. P. : Synthesis and inhibition of $PGE_2$ production of 6,8-disubstituted chrysin derivatives. European J. Med. Chem. 40, 943 (2005). https://doi.org/10.1016/j.ejmech.2005.04.013
  9. Jang, J., Sin, K.-S., Kim, H. P. and Park, H. : Inhibitory activity of 8-aminowogonin analogues against prostaglandin $E_2$ production. Yakhak Hoeji 52, 85 (2008).
  10. 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
  11. 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
  12. 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
  13. Che, H., Yoon, D. H., Kim, T. W., Sung, G.-H. and Park, H. : Synthesis and biological evaluation of militarin derivatives. Yakhak Hoeji 56, 372 (2012).