Synthesis of a Range of Polyhydroxy 8-Aryl Flavones

Synthetic Communications

Volumn 39, Issue 16, 2009, Pages 2935-2948

  Larsen, Lesley ^a   Yoon, Dong Hee ^a   Weavers, Rex T ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

Chalcone cyclization; Selective iodination; Suzuki coupling

Indexed keywords

BORON TRIBROMIDE; CHALCONE DERIVATIVE; DIMETHYL SULFOXIDE; FLAVONE DERIVATIVE; HYDROXYL GROUP; IODINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 67651102760     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802710682     Document Type: Article

References (27)

1. (a) Seeger, T.; Geiger, H.; Zinsmeister, H. D. Isolation and structure elucidation of bartramia-triluteolin, bartramic acid and biflavonoids from the moss. Bartra-mia poiformis. Z. Naturforsch., C: Biosci. 1992, 47, 527-530;
2. (b) Lopez-Saez, J. A. Biflavonoid differentiation in six Bartramia species. Plant System. Evol. 1996, 203, 83-89;
3. (c) Bedir, E.; Tatli, I. I.; Khan, R. A.; Zhao, J.; Takamatsu, S.; Walker, L. A.; Goldman, P.; Khan, I. A. Biologically active secondary metabolites from Ginkgo biloba. J. Agric. Food Chem. 2002, 50, 3150-3155.
4. (a) Baker, W.; Ollis, W. D.; Robinson, K. W. Biflavonyls. The structures of kayaflavone and sotetsuflavone. Proc. Chem. Soc. 1959, 269-270;
5. (b) Baker, W.; Finch, A. C. M.; Ollis, W. D.; Robinson, K. W. The structures of the naturally occurring biflavonyls. J. Chem. Soc. 1963, 1477-1490.
6. (a) Shah, M. V. Synthesis of some bichromonyls, biflavonyls, and 7-methoxy-8-phenyl-2-methylchromone and flavone. Curr. Sci. 1962, 31, 57-58;
7. (b) Khan, H. A.; Ahmad, F.; Rahman, W. Synthesis of 8-(3″0-formyl- formyl-6″0-methoxyphenyl)-5,7,4′-trimethoxyflavone. Indian J. Chem. B 1978, 16B, 845-846.
8. Chandramouli, N.; Murti, V. V. S.; Natarajan, S.; Seshadri, T. R. Synthesis of 8-phenylapigenin trimethyl ether, a model for carbo-carbon linked biflavones. Indian J. Chem. 1972, 10, 1194-1195.
9. (a) Matsumura, H.; Tsuchiya, T.; Imafuku, K. Bull. Chem. Soc. Jap. 1983, 56, 3519-3520;
10. (b) Matsumura, H.; Tsuchiya, T.; Takeda, T.; Imafuku, K. Bull. Chem. Soc. Jap. 1983, 56, 2037-2043.
11. (a) Dao, T. T.; Kim, S. B.; Sin, K.-S.; Kim, S.; Kim, H. P.; Park, H. Synthesis and biological activities of 8-aryl flavones. Arch. Chem. Res. 2004, 27, 278-282;
12. (b) Park, H.; Dao, T. T.; Kim, H. P. Synthesis and inhibition of PGE2 production of 6,8-disubstituted chrysin derivatives. Eur. J. Med. Chem. 2005, 40, 943-948;
13. (c) Fitzmaurice, R. J.; Etheridge, Z. C.; Jumel, E.; Woolfson, D. N.; Caddick, S. Chem. Commun. 2006, 4814-4816.
14. Cotelle, N.; Bernier, J.-L.; Catteau, J.-P.; Pommery, J.; Wallet, J. T.; Gaydou, E. M. Antioxidant properties of hydroxyl-flavones. Free Rad. Biol. Med. 1996, 20, 35-43.
15. Lee, E.-R.; Kim, J.-H.; Kang, Y.-J.; Cho, S.-G. The anti-apoptotic and anti-oxidant effect of eriodictyol on UV induced apoptosis in keratinocytes. Biol. Pharm. Bull. 2007, 30, 32-37.
16. Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J. Synthesis of 8-C-glucosylflavones. Carbohydr. Res. 2001, 334, 183-193.
17. 13C NMR assignments. Tetrahedron Lett. 1994, 35, 5899-5902.
18. Malone, D. J.; Hecht, S. M. Synthesis of a potent and selective inhibitor of p90 Rsk. Org. Lett. 2005, 7, 1097-1099.
19. Pinto, D. C. G A.; Silva, A. M. S.; Calvaleiro, J. A. S. Synthesis of 6,6-(dibromo or diiodo)-5-hydroxy-2-(phenyl or styryl)chromones. Tetrahedron Lett. 1994, 35, 9459-9460.
20. Pinto, D. C. G A.; Silva, A. M. S.; Calvaleiro, J. A. S. Synthesis of 5-hydroxy-2-(phenyl or styryl)chromones and of some halo derivatives. J. Heterocycl. Chem. 1996, 33, 1887-1893.
21. Ahmad, S.; Razaq, S. Synthetic studies of biflavonoids, I. Pakistan J. Sci. Ind. Res. 1971, 14, 40-42.
22. 13C-labelled (+)-catechin and (-)-epicatechin. Eur. J. Org. Chem. 2001, 2379-2384.
23. He, X.; Yang, F.; Lei, X.; Chen, J.; Min, Y. Synthesis of B-ring substituted 5,7-dihydroxyflavanones and their effects on isolated guinea pig hearts. Yiyao Gongye 1988, 19, 447-451.
24. Zaveri, N.; Chao, W.-R.; Bensari, A. Preparation of catechin benzoyl esters as anticancer agents. US Patent 2004110790 A1 20040610, 2004.
25. Kawamoto, H.; Nakatsubo, F.; Murakami, K. Synthesis of condensed tannin derivatives regio specifically linked through a single interflavanoid-linkage and their protein-precipitating capacities. Mokuzai Gakkaishi 1991, 37, 741-747.
26. Sutthanut, K.; Sripanidkulchai, B.; Yenjai, C.; Jay, M. Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parvi-flora by gas chromatography. J. Chromatogr. A 2007, 1143, 227-233.
27. Schultz, A.; Laschat, S.; Diele, S.; Nimtz, M. Tetraphenylethene-derived columnar liquid crystals and their oxidative photocyclization. Eur. J. Org. Chem. 2003, 15, 2829-2839.