Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones

Journal of Pharmacy and Pharmacology

Volumn 59, Issue 12, 2007, Pages 1697-1701

  Bovicelli, Paolo ^a   D'Angelo, Vittoria ^a   Collalto, Daniela ^a   Verzina, Antonio ^a   D'Antona, Nicola ^b   Lambusta, Daniela ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 3' DEMETHOXYSUDACHITIN; CHITIN DERIVATIVE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; BROMINATION; CATALYST; CONFERENCE PAPER; DRUG SYNTHESIS; HELICOBACTER PYLORI; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; OXIDATION; OXYGENATION;

ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; CHEMISTRY, PHARMACEUTICAL; FLAVANONES; FLAVONES; FLAVONOIDS; GLYCOSIDES; MODELS, CHEMICAL; MOLECULAR STRUCTURE;

EID: 36849032208     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.59.12.0012     Document Type: Conference Paper

References (24)

1. Aroonrerk, N., Punjanon, T., Suksamrarn, S., Kongkun S. (2003) Antimycobacterial and antioxidant flavones from Limnophila geoffrayi. Arch. Pharm. Res. 26: 816-820
2. Bacon, R. G. R., Rennison, S. C. (1969) Metal ions and complexes in organic reactions. IX. Copper(I)-catalyzed conversion of aryl halides into alkyl aryl ethers. J. Chem. Soc. (C) 2: 312-315
3. Bernsen, H. J. J. A., van der Kogel, A. J. (1999) Anti-angiogenic therapy in brain tumor models J. Neuro-oncol. 45: 247-255
4. Bovicelli, P., Mincione, E., Antonioletti, R., Bernini, R., Colombari, M. (2001) Selective halogenation of aromatics by dimethyldioxirane and halogen ions. Synth. Commun. 31: 2955-2963
5. Bovicelli, P., Bernini, R., Antonioletti, R., Mincione, E. (2002) Selective halogenation of flavanones. Tetrahedron Lett. 43: 5563-5567
6. Bovicelli, P., Antonioletti, R., Barontini, M., Borioni, G., Bernini, R., Mincione, E. (2005) New convenient synthesis of iridol. An approach to the synthesis of ubiquinones. Tetrahedron Lett. 46: 1255-1257
7. Bovicelli, P., Antonioletti, R., Onori, A., Delogu, G., Fabbri, D., Dettori, M. A. (2006) Regioselective halogenation of biphenyls for preparation of valuable polyhydroxylated biphenyls and diquinones. Tetrahedron 62: 635-639
8. Bovicelli, P., Antonioletti, R., Mancini, S., Causio S., Borioni G., Ammendola, S., Barontini, M. (2007) Expeditious synthesis of hydroxytyrosol and its esters. Synth. Commun. 37: in press.
9. Cotelle, N., Bernier, J.-L., Catteau, J.-P., Pommery, J., Wallet, J.-C., Gaydou, E. M. (1996) Antioxidant properties of hydroxy-flavones. Free Radic. Biol. Med. 20: 35-43
10. Fatma, W., Iqbal, J., Manchanda, V., Shaida, W. A., Rahman, W. (1984) Dehydrogenation of flavanoids with the iodine-dimethyl sulfoxide-sulfuric acid reagent system. J. Chem. Res. (S) 9: 298
11. Iinuma, M., Matsuura, S., Kusuda, K. (1980) Carbon-13 nuclear magnetic resonance (nmr) spectral studies on polysubstituted flavonoids. I. Carbon-13-nmr spectra of flavones. Chem. Pharm. Bull. 28: 708-716
12. Khan, A. T., Goswami, P. (2005) A mild and environmentally acceptable synthetic protocol for chemoselective α-bromination of β-keto esters and 1,3-diketones. Tetrahedron Lett. 46: 4937-4940
13. Marder, M., Viola, H., Wasowski, C., Wolfman, C., Waterman, P. G., Cassels, B. K., Medina, J. H., Paladini, A. C. (1996) 6-Bromoflavone, a high affinity ligand for the central benzodiazepine receptors, is a member of a family of active flavonoids. Biochem. Biophys. Res. Comm. 223: 384-389
14. Matuyama, K., Tamanaka, K., Nishinaga, A., Inada, A., Nakaishi, T. (1989) Conversion of 2′-hydroxychalcones to flavanones catalyzed by cobalt Schiff base complex. Tetrahedron Lett. 30: 4145-4148.
15. Moon, B.-H., Lee, Y.; Shin, C., Lim, Y. (2005) Complete assignments of the 1H and 13C NMR data of flavone derivatives Bull. Kor. Chem. Soc. 26: 603-608
16. Nakagawa, H., Takaishi, Y., Tanaka, N., Tsuchiya, K., Shibata, H., Higuti, T. (2006) Chemical constituents from the peels of Citrus sudachi. J. Nat. Prod. 69: 1177-1179
17. Ramadas, S., Krupadanam, G. L. D. (2004) Enantioselective acylation of (±)-cis-flavan-4-ols catalyzed by lipase from Candida cylindracea (CCL) and the synthesis of enantiopure flavan-4-ones. Tetrah. Asymm. 15: 3381-3391
18. Rho, H. S., Ko, B.-S., Kim, H. K., Ju, Y.-S. (2002) Synthesis of 3-bromo derivatives of flavones. Synth. Commun. 32: 1303-1310
19. Sanicanin, Z., Tabakovic, I. (1986) Electrochemical synthesis of heterocyclic compounds. Part 16. Electrochemical transformations of 2′-hydroxychalcones into flavanoids. Tetrahedron Lett. 27: 407-408
20. Senderowicz, A.M., (1999) Flavopiridol: The first cyclin-dependent kinase inhibitor in human clinical trials. Invest. New Drugs 17: 313-320
21. Senderowicz, A.M. (2001) Development of cyclin-dependent kinase modulators as novel therapeutic approaches for hematological malignancies. Leukemia 15: 1-9
22. Shen, C. C., Chang, Y. S., Ho, Li K. (1993) Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids. Phytochemistry 34: 843-845
23. Stermitz, F.R., Adamovics, J.A., Geigert, J. (1975) Synthesis and photoreactions of sorbophenones. Photochemical synthesis of flavone. Tetrahedron 31: 1593-1595
24. Tapia, A., Rodriguez, J., Theoduloz, C., Lopez, S., Feresin, G. E., Schmeda-Hirschmann, G. (2004) Free radical scavengers and antioxidants from Baccharis grisebachii. J. Ethnopharmacol. 95: 155-161