Synthesis and 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) |
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 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 |