Hemisynthesis of all the O-monomethylated analogues of quercetin including the major metabolites, through selective protection of phenolic functions

Tetrahedron

Volumn 58, Issue 50, 2002, Pages 10001-10009

  Bouktaib, Mohamed ^a,b   Lebrun, Stéphane ^a   Atmani, Aziz ^b   Rolando, Christian ^a  

^a UNIV LILLE   (France)

^b SIDI MOHAMED BEN ABDELLAH UNIVERSITY   (Morocco)

Author keywords

Alkylation; Metabolites; Quercetin

Indexed keywords

3',4' O DIMETHYLQUERCETIN; 3,7 O DIMETHYLQUERCETIN; 4' O METHYLQUERCETIN; 5 O METHYLQUERCETIN; 7 O METHYLQUERCETIN; ISORHAMNETIN; METHYL GROUP; PHENOL DERIVATIVE; QUERCETIN 3 METHYL ETHER; QUERCETIN DERIVATIVE; RHAMNETIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; METHYLATION; PRIORITY JOURNAL; REACTION OPTIMIZATION; REVERSED PHASE LIQUID CHROMATOGRAPHY;

EID: 0037049272     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01306-6     Document Type: Article

References (45)

1. Bohm B.A. Introduction to Flavonoids. 1998;Harwood Academic, Amsterdam.
2. Packer L., Flavonoids and other Polyphenols. Methods in Enzymology. Vol. 335:2001;Academic, San Diego.
3. Hollman P.C.H., Arts I.C.W. J. Sci. Food Agric. 80:2000;1081-1093.
4. Pietta P.G. J. Nat. Prod. 63:2000;1035-1042.
5. Choi J.A., Kim J.Y., Lee J.Y., Kang C.M., Kwon H.J., Yoo Y.D., Kim T.W., Lee Y.S., Lee S.J. Int. J. Oncol. 19:2001;837-844.
6. Yoshizumi M., Tsuchiya K., Kirima K., Kyaw M., Suzaki Y., Tamaki T. Mol. Pharmacol. 60:2001;656-665.
7. Schroeter H., Spencer J.P.E., Rice-Evans C., Williams R.J. Biochem. J. 358:2001;547-557.
8. Wang H.K. Expert Opin. Investig. Drugs. 9:2000;2103-2119.
9. Lamson D.W., Brignall M.S. Altern. Med. Rev. 5:2000;196-208.
10. Gross A., Borcherding D.R., Friedrich D., Sabol J.S. Tetrahedron Lett. 42:2001;1631-1633.
11. Murthi K.K., Dubay M., McClure C., Brizuela L., Boisclair M.D., Worland P.J., Mansuri M.M., Pal K. Bioorg. Med. Chem. Lett. 10:2000;1037-1041.
12. Koga T., Meydani M. Am. J. Clin. Nutr. 73:2001;941-948.
13. Ader P., Wessmann A., Wolffram S. Free Rad. Biol. Med. 28:2000;1056-1067.
14. Manach C., Texier O., Morand C., Crespy V., Régérat F., Demigné C., Rémésy C. Free Rad. Biol. Med. 27:1999;1259-1266.
15. Boulton D.W., Walle U.K., Walle T. J. Pharm. Pharmacol. 51:1999;353-359.
16. Graefe E.U., Derendorf H., Veit M. Int. J. Clin. Pharmacol. Ther. 37:1999;219-233.
17. Graefe E.U., Wittig J., Mueller S., Riethling A.K., Uehleke B., Drewelow B., Pforte H., Jacobasch G., Derendorf H., Veit M. J. Clin. Pharmacol. 41:2001;492-499.
18. Manach C., Morand C., Crespy V., Demigné C., Texier O., Régérat F., Rémésy C. FEBS Lett. 426:1998;331-336.
19. Moon J., Tsushida T., Nakahara K., Terao J. Free Rad. Biol. Med. 30:2001;1274-1285.
20. O'Leary K.A., Day A.J., Needs P.W., Sly W.S., O'Brien N.M., Williamson G. FEBS Lett. 503:2001;103-106.
21. Beutler J.A., Hamel E., Vlietinck A.J., Haemers A., Rajan P., Roitman J.N., Cardellina J.H. II, Boyd M.R. J. Med. Chem. 41:1998;2333-2338.
22. Bennett M., Burke A.J., O'Sullivan W.I. Tetrahedron. 52:1996;7163-7178.
23. Boers F., Deng B.-L., Lemière G., Lepoivre J., De Groot A., Dommisse R., Vlietinck A.J. Arch. Pharm. Pharm. Med. Chem. 330:1997;313-316.
24. Caldwell S.T., Crozier A., Hartley R.C. Tetrahedron. 56:2000;4101-4106.
25. Tanaka H., Stohlmeyer M.M., Wandless T.J., Taylor L.P. Tetrahedron Lett. 41:2000;9735-9739.
26. Fougerousse A., Gonzalez E., Brouillard R. J. Org. Chem. 65:2000;583-586.
27. Rao K.V., Owoyale J.A. J. Heterocycl. Chem. 13:1976;1293-1295.
28. Jurd L. J. Org. Chem. 27:1962;1294-1297.
29. Jurd L. J. Am. Chem. Soc. 80:1958;5531-5536.
30. Farkas L., Vermes B., Nogradi M. Acta Chim. Hung. 73:1972;107-111.
31. Cren-Olivé C., Déprez S., Lebrun S., Coddeville B., Rolando C. Rapid Commun. Mass Spectrom. 14:2000;2312-2319.
32. Pacheco H., Grouiller A. Bull. Soc. Chim. Fr. 1965;779-785.
33. Farkas L., Vermes B., Nógrádi M. Chem. Ber. 105:1972;3505-3510.
34. Picq M., Prigent A.F., Chabannes B., Pacheco H. Tetrahedron Lett. 25:1984;2227-2230.
35. Slabbert N.P. Tetrahedron. 33:1977;821-824.
36. Alluis B., Dangles O. Helv. Chim. Acta. 84:2001;1133-1156.
37. Jain A.C., Pankajamani K.S., Seshadri T.R. J. Sci. Ind. Res. (India). 1953;127-131.
38. Yang C.H., Braymer H.D., Murphy E.L., Chorney W., Scully N., Wender S.H. J. Org. Chem. 25:1960;2063-2064.
39. Cren-Olivé C., Lebrun S., Hapiot P., Pinson J., Rolando C. Tetrahedron Lett. 41:2000;5847-5851.
40. Cren-Olivé C., Lebrun S., Rolando C. J. Chem. Soc., Perkin Trans. 1. 2002;821-830.
41. Jurd L. J. Org. Chem. 27:1962;872-875.
42. Bertha B., Diaz J.G., Herz W. Phytochemistry. 31:1992;4374-4375.
43. Le Quesne P.W., Levery S.B., Menachery M.D., Brennan T.F., Raffauf R.F. J. Chem. Soc., Perkin Trans. 1. 1978;1572-1580.
44. Wu J.B., Chun Y.T., Ebikuza Y., Sankawa U. Chem. Pharm. Bull. 39:1991;3272-3275.
45. Itokawa H., Suto K., Takeya K. Chem. Pharm. Bull. 29:1981;254-256.