Browse > Article

Synthesis and $PGE_2$ Inhibitory Activity of 5,7-Dihydroxyflavones and Their Ο-Methylated Flavone Analogs  

Dao, Tran-Thanh (College of Pharmacy, Kangwon National University)
Chi, Yeon-Sook (College of Pharmacy, Kangwon National University)
Kim, Jeong-Soo (College of Pharmacy, Kangwon National University)
Kim, Hyun-Pyo (College of Pharmacy, Kangwon National University)
Kim, Sang-Hee (College of Pharmacy, Seoul National University)
Park, Haeil (College of Pharmacy, Kangwon National University)
Publication Information
Archives of Pharmacal Research / v.26, no.5, 2003 , pp. 345-350 More about this Journal
Abstract
5,7-Dihydroxyflavones and their Ο-methylated flavone analogs were prepared and evaluated their anti-inflammatory activity to decipher the structure-activity relationships. Most of the analogs were achieved from 2,4,6-trihydroxyacetophenone in 4 steps. 5,7-Dihydroxy-4 -methoxyflavone (4c) and 7-hydroxy-4 ,5-dimethoxyflavone(6c) were prepared following a different synthetic pathway. Among the synthetic flavones tested, 5-hydroxy-7-methoxyflavone analogs (3a-3e) showed moderate inhibitory activities of $PGE_2$ production from LPS-induced RAW 264.7 cells.
Keywords
5,7-Dihydroxyflavones; Ο-Methylated flavone analogs; Anti-inflammatory activity; Cyclooxygenase-2; $PGE_2$ production;
Citations & Related Records

Times Cited By Web Of Science : 10  (Related Records In Web of Science)
Times Cited By SCOPUS : 5
연도 인용수 순위
1 Chi, Y. S., Cheon, B. S., and Kim, H. P., Effect of wogonin, a plant flavone from Scutellaria radix, on the suppression of cyclooxygenase-2 and the induction of inducible nitric oxide synthase in lopopolysaccharide-treated RAW 264.7 cells. Biochem. Pharmacol., 61, 1195-1203 (2001)   DOI   PUBMED   ScienceOn
2 Gabor, M., Anti-inflammatory and antiallergy properties of flavonoids. In Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships; Alan R. Liss: New York, 1986; p 471-480
3 Topliss, J. G., A manual method for applying the Hanschapproach to drug design. J. Med. Chem., 20, 463-469 (1977)   DOI   PUBMED
4 Yasukawa, K., Takido, M., Takeuchi, M., and Nakagawa, S., Effect of chemical constituents from plants on 12-O-tertradecanoylphorbol-13-acetatate-induced inflammation in mice. Chem. Pharm. Bull., 37, 1071-1073 (1989)   DOI   PUBMED   ScienceOn
5 Liang, Y.-C., Huang, Y.-T., Tsai, S.-H., Shiau, S.-Y., Chen, C.-F., and Lin, J.-K., Suppression of inducible cyclooxygenase and inducible nitric oxide synthase by apigenin and related flavonoids in mouse macrophages. Carcinogenesis, 20, 1945-1952 (1999)   DOI   ScienceOn
6 Rao, K. V., Rao, K., and Seshadri, T. R., New synthesis of wogonin. Chem. Abstr., 43, 638-639 (1949)
7 Kim, H. K., Cheon, B. S., Kim, Y. H., Kim, S. Y., and Kim, H. P., Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structural-activity relationships. Biochem. Pharmacol., 58, 759-765 (1999)   DOI   PUBMED   ScienceOn
8 Nakazawa, K., Syntheses of nuclear-substituted flavonoids and allied compounds. IX. Syntheses of tetramethyl ether and dimethyl ether of Ginkgetin. Chem. Pharm. Bull., 10, 1032-1038 (1962)   DOI
9 Vickery, E. H., Pahler, L. F., and Eisenbraun, E. J., Selective Odemethylation of catechol ethers. Comparison of boron tribromide and iodotrimethylsilane. J. Org. Chem., 44, 4444-4446 (1979)   DOI
10 Kim, Y. P., Yamada, M., Lim, S. S., Lee, S. H., Ryu, N., Shin, K. H., and Okuchi, K., Inhibition of tectorigenin and tectoridin of prostaglandin $E_{2} production and cyclooxygenase-2 induction in rat peritoneal macrophages. Biochem. Biophys. Acta, 1438, 399-409 (1999)   DOI   ScienceOn
11 Kim, H. P., Son, K. H., Chang, H. W., and Kang, S. S., Effects of naturally occurring flavonoids on inflammatory responses and their action mechanism. Nat. Prod. Sci., 6, 170-178 (2000)
12 Strichtenoth, D. O., and Frolich, J. C., Nitric oxide and inflammatory joint diseases. Br. J. Rheumatol., 37, 246-257 (1998)   DOI   PUBMED
13 Needleman, P., and Isakson, P., The discovery and function of COX-2. J. Rhematol., 24(Suppl. 49), 6-8 (1997)
14 Lewis, D. A., Anti-inflammatory drugs from plant and marine sources. In flavonoids; Berkhauser Verlag: Basel, 1989; Suppl. Vol. 27; p137-165
15 Kosmeder, J. W., Moriarty, R. M., Pezzuto, J. M., Song, L. L., and Moon, R. C. Use of 4’-bromoflavone in a cancer chemopreventative composition and method. US Patent 6,046,231, 2000
16 Parker, K. A., and Petraitis, J. J., Synthesis of ansamycin: An approach to the naphthoquinone portion of the rifamycins and streptovaricins. Tetrahedron Lett., 22, 397-400 (1981)   DOI   ScienceOn