Synthesis of Selectively Protected Genistein Derivatives

Synthetic Communications

Volumn 33, Issue 23, 2003, Pages 4111-4121

  Szeja, Wiesław ^a   Pastuch, Gabriela ^a   Wandzik, Ilona ^a   Kuźnik, Nikodem ^a   Grynkiewicz, Grzegorz ^b  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

^b INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

Author keywords

Acylation; Genistein; Silylation

Indexed keywords

GENISTEIN; GENISTEIN DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION KINETICS; REACTION ANALYSIS; SILYLATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0344234453     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120026353     Document Type: Article

References (12)

1. Dewick, P.M. The isoflavonoids. In The Flavonoids, Advances in Research Since 1986; Harborne, J.B., Ed.; Chapman and Hall: London, 1994; 117-238.
2. Dixon, R.A. Isoflavonoids: biochemistry, molecular biology, and biological functions. In Comprehensive Natural Products Chemistry; Barton, D.H.R., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Amsterdam, 1999; Vol. 1, 773-824.
3. Dixon, R.A.; Ferreira, D. Genistein. Phytochemistry 2002, 60, 205-211.
4. Grynkiewicz, G. Synthetic Genistein as a Prospective Active Ingredient for Nutrition and Medicine. Pol. J. Food Nutr. Sci. 2002, 11/52 (SI 2), 99-105.
5. Balasubramanian, S.; Nair, M.G. An Efficient "One-Pot" Synthesis of Isoflavones. Synth. Commun. 2000, 30, 469-484.
6. Lewis, P.; Kaltia, S.; Wähälä, K. The Phase Transfer Catalysed Synthesis of Isoflavone-O-glucosides. J. Chem. Soc. Perkin Trans. 1. 1998, 2481-2484.
7. Lewis, P.T.; Wähälä, K., Hoikkala, A.; Mutikainen, I.; Meng, Q.-H.; Adlercreutz, H.; Tikkanen, M.J. Synthesis of Antioxidant Isoflavone Fatty Acid Esters. Tetrahedron 2000, 56, 7805-7810.
8. Mazurek, A.P.; Kozerski, L.; Sadlej, J.; Kawȩcki, R.; Bednarek, E.; Sitkowski, J.; Dobrowolski, J.C.; Maurin, J.K.; Biniecki, K.; Witowska, J.; Fiedor, P.; Pachecka, J. Genistein Complexes with Amines: Structure and Properties. J. Chem. Soc., Perkin Trans. 2, 1998, 1223-1230.
9. Polkowski, K.; Dobrowolski, J.C.; Pachecka, J.; Mazurek, A.P. Genistein and its Complexes. Part III. Experimental and Quantum-Chemical Semiempirical Studies. Acta Polon. Pharmac.-Drug Res. 1999, 56, 109-116.
10. Van Look, G.; Simchen, G.; Heberle, J. Silyating Agents; Fluka Chemie AG. Switzerland 1995; 4-127.
11. Greene, T.W.; Wuts, P.G.M. Protection for the hydroxyl group, including 1,2- and 1,3-diols. In Protective Groups in Organic Synthesis; 2nd Ed.; John Wiley & Sons Inc.: New York, Chichester, Brisbane, Toronto, Singapore, 1991; 114-148.
12. -3) is located close to atom Si 1 (0.33 Å). Crystallographic data for the structure reported in this article have been deposited with the Cambridge Crystallographic Data Centre as deposition No. CCDC 200812. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. [Fax: +44(0)1223 336033; E-mail: deposit@ccdc.cam.ac.uk].