Synthesis 2009(11): 1811-1814  
DOI: 10.1055/s-0029-1216791
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Thioflavanone and Flavanone Derivatives by Cyclization of Chalcones

Wojciech Konieczny*, Marek Konieczny
Department of Organic Chemistry, Medical University of Gdańsk, 80-416 Gdańsk, Poland
Fax: +48(58)3493145; e-Mail: wkonieczny@amg.gda.pl;
Further Information

Publication History

Received 31 December 2008
Publication Date:
04 May 2009 (online)

Abstract

Chalcones bearing suitably positioned protected 2′-sulfanyl or 6′-hydroxy groups cyclize to form the corresponding thioflavanones and flavanones, respectively. The thioflavanones were prepared by a new method involving deprotection of the sulfanyl group under alkaline conditions. These reactions provide a route to new biologically interesting molecules.

    References

  • 1a

    Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-Activity Relationships, Proceedings of a Symposium Held in Buffalo, New York, July 22-26, 1985; Cody, V.; Middleton, E. Jr.; Harborne, J. B., Eds.; Liss: New York, 1986.

  • 1b Das A. Wang JH. Lien EJ. Prog. Drug Res.  1994,  42:  133 
  • 1c Middleton E. Kandaswami C. Theoharides TC. Pharmacol. Rev.  2000,  52:  673 
  • 1d Pietta P.-G. J. Nat. Prod.  2000,  63:  1035 
  • 1e Boumendjel A. Di Pietro A. Dumontet C. Barron D. Med. Res. Rev.  2002,  22:  512 
  • 1f Hodek P. Trefil P. Stiborova M. Chem.-Biol. Interact.  2002,  139:  1 
  • 1g Boumendjel A. Curr. Med. Chem.  2003,  10:  2621 
  • 1h Flavonoids in Health and Disease   2nd ed.:  Rice-Evans C. Packer L. Marcel Dekker; New York: 2003. 
  • 1i Rice-Evans C. Free Radical Biol. Med.  2004,  36:  827 
  • 1j Kim HP. Son KH. Chang HW. Kang SS. J. Pharmacol. Sci.  2004,  96:  229 
  • 1k Lawrence NJ. McGown AT. Curr. Pharm. Des.  2005,  11:  1679 
  • 1l Botta B. Vitali A. Menendez P. Misiti D. Delle Monache G. Curr. Med. Chem.  2005,  12:  713 
  • 1m Ni LM. Meng CQ. Sikorski JA. Expert Opin. Therap. Pat.  2004,  14:  1669 
  • 2 Balint J. Bognar R. Rakosi M. In Organic Sulfur Chemistry   Bernardi F. Csizmadia IG. Mangini A. Elsevier; Amsterdam: 1985.  p.660 
  • 3a Nakazumi H. Ueyama T. Kitao T. J. Heterocycl. Chem.  1984,  21:  193 
  • 3b Nakazumi H. Ueyama T. Kitao T. J. Heterocycl. Chem.  1985,  22:  1593 
  • 3c Nakazumi H. Ueyama T. Sonoda H. Kitao T. Bull. Chem. Soc. Jpn.  1984,  57:  2323 
  • 3d Nakazumi H. Kobara Y. Kitao T. J. Heterocycl. Chem.  1992,  29:  135 
  • 4 Rimbault CG. inventors; US Patent  4,885,298. 
  • 5 Dhanak D. Keenan RM. Burton G. Kaura A. Darcy MG. Shah DH. Ridgers LH. Breen A. Lavery P. Tew DG. West A. Bioorg. Med. Chem. Lett.  1998,  8:  3677 
  • 6 Wang H.-K. Bastow KF. Cosentino LM. Lee KH. J. Med. Chem.  1996,  39:  1975 
  • 7 Dekermendjian K. Kahnberg P. Witt M.-R. Sterner O. Nielsen M. Liljefors T. J. Med. Chem.  1999,  42:  4343 
  • 8 Kataoka T. Watanabe S. Mori E. Kadomoto R. Tanimura S. Kohno M. Bioorg. Med. Chem.  2004,  12:  2397 
  • 9 Bates DK. Li K. J. Org. Chem.  2002,  67:  8662 
  • 10 Taylor AW. Dean DK. Tetrahedron Lett.  1988,  29:  1845 
  • 11 Kataoka T. Watanabe S.-i. Mori E. Kadomoto R. Tanimura S. Kohno M. Bioorg. Med. Chem.  2004,  12:  2397 
  • 12 Konieczny MT. Horowska B. Kunikowski A. Konopa J. Wierzba K. Yamada Y. Asao T. J. Org. Chem.  1999,  64:  359 
  • 13 Konieczny MT. Konieczny W. Sabisz M. Skadanowski A. Wakieć R. Augustynowicz-Kopeć E. Zwolska Z. Eur. J. Med. Chem.  2007,  42:  729 
  • 14 Konieczny MT. Konieczny W. Okabe S. Tsujimoto H. Suda Y. Wierzba K. Chem. Pharm. Bull.  2006,  54:  350 
  • 15 Konieczny MT. Konieczny W. Wolniewicz S. Wierzba K. Suda Y. Sowiński P. Tetrahedron  2005,  61:  8648