Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 1, 2011, Pages 186-196

  Lewin, Guy ^a   Shridhar, Narayan Bhat ^b   Aubert, Genevive ^c   Thoret, Sylviane ^c   Dubois, Joëlle ^c   Cresteil, Thierry ^c  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b VETERINARY COLLEGE   (India)

^c INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

Antimitotic; Antiproliferative activity; Calycopterin; Calycopteris floribunda; Combretastatins; Flavones; Tubulin

Indexed keywords

3' AMINO 3,5,6,7,8,4' HEXAMETHOXY FLAVONE; 3' AMINO 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' AMINO 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' AMINO 5,6 DIHYDROXY 3,7,8,4' TETRAMETHOXY FLAVONE; 3' AMINO 5,7 DIHYDROXY 3,6,8,4' TETRAMETHOXY FLAVONE; 3' AMINO 5,8 DIHYDROXY 3,6,7,4' TETRAMETHOXY FLAVONE; 3' AMINOMETHYL 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' CYANO 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' DIMETHYLAMINO 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' DIMETHYLAMINOMETHYL 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' FORMYL 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3' FORMYL CALYCOPTERIN; 3' HYDROXYMETHYL 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 3',3' BIFLAVONE; 3',5' DIODO 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; 5 HYDROXY 3' IODO 3,6,7,8,4' PENTAMETHOXY FLAVONE; 5 HYDROXY 3' NITRO 3,6,7,8,4' PENTAMETHOXY FLAVONE; 5 HYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE(CALYCOPTERIN 4' O METHYL ETHER); 5,3' DIAMINO 3,6,7,8,4' PENTAMETHOXY FLAVONE; 5,3' DIHYDROXY 3,6,7,8,4' PENTAMETHOXY FLAVONE; CALYCOPTERIN; DOXORUBICIN; FLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALYCOPTERIS FLORIBUNDA; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MEDICINAL PLANT; STRUCTURE ACTIVITY RELATION;

CELL LINE, TUMOR; CELL PROLIFERATION; COMBRETACEAE; FLAVONES; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

CALYCOPTERIS FLORIBUNDA;

EID: 78650747032     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.11.035     Document Type: Article

References (29)

1. J.A. Beutler, E. Hamel, A.J. Vlietinck, A. Haemers, P. Rajan, J.N. Roitman, J.H. Cardellina II, and M.R. Boyd J. Med. Chem. 41 1998 2333
2. N. Fang, M. Leidig, and T.J. Mabry Phytochemistry 25 1986 927
3. J.J. Lichius, O. Thoison, A. Montagnac, M. Païs, F. Guéritte-Voegelein, and T. Sévenet J. Nat. Prod. 57 1994 1012
4. Q. Shi, L. Li, J.-J. Chang, C. Autry, M. Kozuka, T. Konoshima, J.R. Estes, C.M. Lin, E. Hamel, A.T. McPhail, D.R. McPhail, and K.-H. Lee J. Nat. Prod. 58 1995 475
5. G. Lewin, A. Maciuk, S. Thoret, G. Aubert, J. Dubois, and T. Cresteil J. Nat. Prod. 73 2010 702
6. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani J. Med. Chem. 49 2006 3033
7. W. Karrer Helv. Chim. Acta 17 1934 1560
8. A.N. Ratnagiriswaran, K.R. Sehra, and K. Venkataraman Biochem. J. 28 1934 1964
9. P. Sreekanth, K. Narayana, N.B. Shridhar, and B. Avinash J. Ethnopharmacol. 107 2006 229
10. J. Quintin, C. Roullier, S. Thoret, and G. Lewin Tetrahedron 62 2006 4038
11. J. Quintin, D. Buisson, S. Thoret, T. Cresteil, and G. Lewin Bioorg. Med. Chem. Lett. 19 2009 3502
12. B. Milligan J. Org. Chem. 48 1983 1495
13. S. Uemura, A. Toshimitsu, and M. Okano J. Chem. Soc., Perkin Trans. 1 1978 1076
14. P.S. Sarin, and T.R. Seshadri Tetrahedron 8 1960 64
15. R.S. Gupta, T.R. Seshadri, and G.R. Sood Phytochemistry 12 1973 2539
16. T. Ishiyama, M. Murata, and N. Miyaura J. Org. Chem. 60 1995 7508
17. G. Goulette, B. Gaux, and P. Le Henaff C.R. Acad. Sci., Ser. C 281 1975 543
18. D.E. Zembower, and H. Zhang J. Org. Chem. 63 1998 9300
19. X. Zheng, W.-D. Meng, and F.-L. Qing Tetrahedron Lett. 45 2004 8083
20. G. Stavber, M. Zupan, and S. Stavber Tetrahedron Lett. 48 2007 2671
21. T. Akama, Y. Shida, T. Sugaya, H. Ishida, K. Gomi, and M. Kasai J. Med. Chem. 39 1996 3461
22. T. Akama, H. Ishida, Y. Shida, U. Kimura, K. Gomi, H. Saito, E. Fuse, S. Kobayashi, N. Yoda, and M. Kasai J. Med. Chem. 40 1997 1894
23. T. Akama, H. Ishida, U. Kimura, K. Gomi, and H. Saito J. Med. Chem. 41 1998 2056
24. C. Lecoutey, C. Fossey, L. Demuynck, F. Lefoulon, F. Fabis, and S. Rault Tetrahedron 64 2008 11243
25. S. Li, M.-H. Pan, C.-S. Lai, C.-Y. Lo, S. Dushenkov, and C.-T. Ho Bioorg. Med. Chem. 15 2007 3381
26. A.M. Bernard, M.R. Ghiani, P.P. Piras, and A. Rivoldini Synthesis 1989 287
27. M. Lopez-Lazaro, M. Galvez, C. Martin-Cordero, and M.J. Ayuso Stud. Nat. Prod. Chem. 27 2002 891
28. E. Rodriguez, G. Vander Velde, T.J. Mabry, S. Sankara Subramanian, and A.G.R. Nair Phytochemistry 11 1972 2311
29. F. Zavala, D. Guénard, J.-P. Robin, and E. Brown J. Med. Chem. 23 1980 546