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Synthesis 2001(9): 1363-1367
DOI: 10.1055/s-2001-15223
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Polyhydroxylated Derivatives of Phenyl Vinyl Sulfone as Structural Analogs of Chalcones

Marek T. Konieczny*a, Barbara Horowskaa, Antoni Kunikowskia, Jerzy Konopaa, Konstanty Wierzbab, Yuji Yamadab, Tetsuji Asaob
a Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdansk, 80-952 Gdansk, Poland
Fax: +48(58)3493206; e-Mail: markon@amedec.amg.gda.pl;
b Taiho Pharmaceutical Company, Hanno Research Center, Yaoroshi, Hanno-city, Saitama, 357, Japan
Further Information

Publication History

Received 20 November 2000
Publication Date:
24 September 2004 (online)

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Abstract

A series of polyhydroxylated phenyl vinyl sulfones was prepared by phase transfer condensation of suitable phenyl methyl sulfones with substituted benzaldehydes. The compounds were prepared as structural analogs of biologically active chalcones. One of the compounds was cyclized to a derivative of 2,3-dihydro-2-phenyl-1,4-benzoxathiin-4,4-dioxide, a heterocyclic system closely resembling flavanones.

Key words

phenyl vinyl sulfones - 1,4-benzoxathiin-4,4-dioxide - chalcones - flavanones

    References

  • 1 Dhar DN. The Chemistry of Chalcones and Related Compounds   Wiley; New York: 1981. 
    Google Scholar
  • 2 Hsieh HK. Lee TH. Wang JP. Wang JJ. Lin CN. Pharm. Res.  1998,  15:  39 
    CrossrefGoogle Scholar
  • 3 Lin CN. Lee TH. Hsu MF. Wang JP. Ko FN. Teng CM. J. Pharm. Pharmacol.  1997,  49:  530 
    CrossrefGoogle Scholar
  • 4 Powers DG. Casebier DS. Fokas D. Ryan WR. Troth JR. Coffen DL. Tetrahedron  1998,  54:  4085 
    CrossrefGoogle Scholar
  • 5 Simpkins NS. Sulphones in Organic Synthesis   Pergamon Press; Oxford: 1993. 
    Google Scholar
  • 6 The Chemistry of Sulphones and Sulphoxides   Patai S. Rappoport Z. Stirling C. Wiley; Chichester: 1988. 
    Google Scholar
  • 7 Simpkins NS. Tetrahedron  1990,  46:  6951 
    CrossrefGoogle Scholar
  • 8 Magnus PD. Tetrahedron  1977,  33:  2019 
    CrossrefGoogle Scholar
  • 9a Reddy PE, and Reddy RMV. inventors; PCT Int. Appl.  WO9918068. 
  • 10a Konopa JK, Konieczny MT, Horowska BJ, Kunikowski AJ, Asao T, Nishino H, and Yamada Y. inventors; Jpn. Patent JP  9003037. 
  • 11 Pathak D. Pathak K. Singla AK. Fitoterapia  1991,  62:  371 
    Google Scholar
  • 12 Das A. Wang JH. Lien EJ. Prog. Drug Res.  1994,  42:  134 
    Google Scholar
  • 13 Sogawa S. Nihro Y. Ueda H. Izumi A. Miki T. Matsumoto H. Satoh TJ. Med. Chem.  1993,  36:  3904 
    CrossrefGoogle Scholar
  • 14 Miyahara M. Ohtaka H. Katayama H. Tatsumi Y. Miyaichi Y. Tomimori T. Yakugaku Zasshi  1993,  113:  133 
    Google Scholar
  • 15 Konieczny MT. Horowska B. Kunikowski A. Konopa J. Wierzba K. Yamada Y. Asao T. J. Org. Chem.  1999,  64:  359 
    CrossrefGoogle Scholar
  • 16a Konopa JK, Konieczny MT, Horowska BJ, Kunikowski AJ, Asao T, Nishino H, and Yamada Y. inventors; Jpn. Patent JP  9025278. 
  • 17 Cardillo G. Savoia D. Umano-Ronchi A. Synthesis  1975,  453 
    Article in Thieme ConnectGoogle Scholar
  • 18 Baliah V. Ganapathy K. Ananthapadmanabhan S. Indian J. Chem., Sect. B  1982,  21:  208 
    Google Scholar
  • 19 Julia M. Righini A. Uguen D. J. Chem. Soc., Perkin Trans. 1  1978,  1646 
    CrossrefGoogle Scholar
  • 20 Reddy MVR. Reddy S. Sulfur Lett.  1987,  7:  43 
    Google Scholar
  • 21 Reddy DB. Murthy KR. Seshamna T. Sulfur Lett.  1990,  12:  73 
    Google Scholar
  • 22 Villemin D. Ben Alloum A. Synth. Commun.  1991,  21:  63 
    Google Scholar
  • 23 Walker J. J. Chem. Soc.  1945,  630 
    Google Scholar
  • 24 Scribner RM. J. Org. Chem.  1966,  31:  3671 
    CrossrefGoogle Scholar
  • 25 Pagani G. Maiorana S. Chim. Ind. (Milan)  1971,  53:  468 
    Google Scholar
  • 26 Parham WE. Willette GL. J. Org. Chem.  1960,  25:  53 
    Google Scholar
  • 27 Parham WE. Jones JD. J. Am. Chem. Soc.  1954,  76:  1068 
    CrossrefGoogle Scholar
  • 28 Cao S. Fan A. Huang Z. Zhang Z. Synth. Commun.  1996,  26:  3979 
    Google Scholar
  • 29a Cao S. Zhang Z. Huaxue Shiji  1999,  21:  176 
    Google Scholar