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Synthesis 2003(18): 2844-2850  
DOI: 10.1055/s-2003-42442
PAPER
© Georg Thieme Verlag Stuttgart · New York

Formation of Two 4-Imidazolylmethylphosphonium Salts and their Synthetic Studies Toward Histamine H3-Ligands

Shinya Harusawaa, Makoto Kawamuraa, Shuji Koyabua, Tomoko Hosokawaa, Lisa Arakia, Yasuhiko Sakamotob, Takeshi Hashimotoc, Yumiko Yamamotoc, Atsushi Yamatodanic, Takushi Kurihara*a
a Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan
Fax: +81(72)6901086; e-Mail: kurihara@gly.oups.ac.jp;
b R&D Division, AZWELL, Inc., 2-24-3, Sho, Ibaraki, Osaka 567-0806, Japan
Fax: +81(72)6224999; e-Mail: ya-sakamoto@azwell.co.jp;
c Graduate School of Allied Health Sciences, Faculty of Medicine, Osaka University, Osaka 565-0871, Japan
Fax: +81(6)68792562; e-Mail: yamatoda@sahs.med.osaka-u.ac.jp;
Further Information

Publication History

Received 25 August 2003
Publication Date:
21 October 2003 (online)

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Abstract

A simple and convenient preparation of {[1H-imidazol-4(5)-yl]methyl}triphenylphosphonium chloride (5) is described. The phosphonium salt 5 could be applied to the synthesis of 1-[1H-imidazol-4(5)-yl]-5-arylpentan- or 6-arylhexan-3-ones 4a-d exhibiting histamine H3-antagonistic activities via a 1,3-diazafulvene intermediate 6 generated from 5. Further, two-methylene-enlongated homolog 3 of imifuramine was efficiently synthesized, starting from Wittig olefination of aldehyde 24 using [(1-tritylimidazol-4-yl)methyl]triphenylphosphonium chloride 7.

Key words

imidazole - histamine H3-ligand - phosphonium salts - diazafulvene - Wittig olefination

    References

  • 1 Grimmett MR. In Comprehensive Heterocyclic Chemistry II: Imidazoles   Vol. 3:  Katritzky AR. Rees CW. Scriven EF. Pergamon; Oxford: 1996.  p.77-220  
    Google Scholar
  • For reviews, see:
  • 2a Stark H. Schlicker E. Schunack W. Drugs Future  1996,  21:  507 
    Google Scholar
  • 2b Leurs R. Blandian P. Tedford C. Timmerman H. TIPS  1998,  19:  177 
    Google Scholar
  • 2c Watanabe T. Timmerman H. Yanai K. Histamine Reseach in the New Millennium   Elsevier; Amsterdom: 2001. 
    Google Scholar
  • 3 For a review, see: Hough LB. Mol. Pharmacol.  2001,  59:  415 
    Google Scholar
  • 4a Harusawa S. Imazu T. Takashima S. Araki L. Ohishi H. Kurihara T. Yamamoto Y. Yamatodani A. Tetrahedron Lett.  1999,  40:  2561 
    CrossrefGoogle Scholar
  • 4b Harusawa S. Imazu T. Takashima S. Araki L. Ohishi H. Kurihara T. Sakamoto Y. Yamamoto Y. Yamatodani A. J. Org. Chem.  1999,  64:  8608 
    CrossrefGoogle Scholar
  • 5 Hashimoto T. Harusawa S. Araki L. Zuiderveld OP. Smit MJ. Imazu T. Takashima S. Yamamoto Y. Sakamoto Y. Kurihara T. Leurs R. Bakker R. Yamatodani A. J. Med. Chem.  2003,  46:  3162 
    CrossrefGoogle Scholar
  • 6a Vollinga RC. Menge WMPB. Leurs R. Timmerman H. J. Med. Chem.  1995,  38:  266 
    CrossrefPubMedGoogle Scholar
  • 6b Vollinga RC. Menge WMPB. Leurs R. Timmerman H. J. Med. Chem.  1995,  38:  2244 
    CrossrefPubMedGoogle Scholar
  • 6c De Esch IJP. Gaffar A. Menge WMPB. Timmerman H. Bioorg. Med. Chem.  1999,  7:  3003 
    CrossrefPubMedGoogle Scholar
  • 6d Kazuta Y. Hirano K. Natsume K. Yamada S. Kimura R. Matsumoto S. Furuichi K. Matsuda A. Shuto S. J. Med. Chem.  2003,  46:  1980 
    CrossrefPubMedGoogle Scholar
  • 7 Harusawa S. Koyabu S. Inoue Y. Sakamoto Y. Araki L. Kurihara T. Synthesis  2002,  1072 
    Article in Thieme ConnectGoogle Scholar
  • 8a Lassalle G, Purcell T, Galtier D, Williams PH, and Galli F. inventors; Eur. Pat. Appl., EP  565396. 
  • 8b Perard S, Zard L, and Rossey G. inventors; Eur. Pat. Appl., EP  614986. 
  • 8c Lassalle G, Galtier D, and Galli F. inventors; Eur. Pat. Appl., EP  643047. 
  • 8d Galtier D, and Lassalle G. inventors; Eur. Pat. Appl., EP  643046. 
  • 8e Lassalle G, Galtier D, and Galli F. inventors; Fr Demande., FR  2710067. 
  • 8f Lassalle G, Purcell T, Galtier D, Williams PH, and Galli F. inventors; US Pat., US  5453430. 
  • 8g Yokohama S, Takeda Y, Kawakoshi K, and Yamamoto K. inventors; Jpn. Kokai Tokkyo Koho, JP  11279156. 
  • 9a Bruice TC. Herz JL. J. Am. Chem. Soc.  1964,  86:  4109 
    CrossrefPubMedGoogle Scholar
  • 9b Harusawa S. Murai Y. Moriyama H. Imazu T. Ohishi H. Yoneda R. Kurihara T. J. Org. Chem.  1996,  61:  4405 
    CrossrefPubMedGoogle Scholar
  • 10a Coates IH, Charles NP, and William OA. inventors; Eur. Pat. Appl., EP  306323. 
    Crossref
  • 10b Cordi AA. Snyers MP. Giraud-Mangin D. Van der Maesen C. Van Hoeck JP. Beuze S. Ellens E. Napora F. Gillet CL. Gorissen H. Calderon P. Remacle MD. Janssens de Varebeke P. Van Dorsser W. Roba J. Eur. J. Med. Chem.  1990,  25:  557 
    CrossrefGoogle Scholar
  • 11a Zbiral E. Hugl E. Phosphorus  1972,  2:  29 
    CrossrefGoogle Scholar
  • 11b Zbiral E. Synthesis  1974,  775 
    CrossrefGoogle Scholar
  • 11c Webb RL. Lewis JJ. J. Heterocycl. Chem.  1981,  18:  1301 
    CrossrefGoogle Scholar
  • 12a Staab HA. Datta AP. Angew. Chem., Int. Ed. Engl.  1964,  3:  132 
    CrossrefGoogle Scholar
  • 12b Devos A. Remion J. Frisque-Hesbain AM. Colens A. Ghosez L. J. Chem. Soc., Chem. Commun.  1979,  1180 
    CrossrefGoogle Scholar
  • 12c Villeneuve GB. Chan TH. Tetrahedron Lett.  1997,  38:  6489 
    CrossrefGoogle Scholar
  • 13 Chaturvedi N. Goodman M. Bowers C. Int. J. Peptide Protein Res.  1981,  17:  72 
    Google Scholar
  • 14 Huckin SN. Weiler L. J. Am. Chem. Soc.  1974,  96:  1082 
    CrossrefGoogle Scholar
  • 15a Vollinger RC. Zuiderveld OP. Scheerens H. Bast A. Timmerman H. Methods Find Exp. Clin. Pharmacol.  1992,  14:  747 
    Google Scholar
  • 15b Hashimoto T. Hidaka R. Yamamoto Y. Harusawa S. Araki L. Kurihara T. Sakamoto Y. Yamatodani A. Inflamm. Res.  2003,  in press 
    Google Scholar
  • 16 Koert U. Stein M. Wagner H. Liebings Ann.  1995,  1415 
    Google Scholar
  • 18a Frigerio M. Santagostino M. Sputore S. Palmisano G. J. Org. Chem.  1995,  60:  7272 
    CrossrefGoogle Scholar
  • 18b Frigerio M. Santagostino M. Tetrahedron. Lett.  1994,  35:  8019 
    CrossrefGoogle Scholar
  • 18c Dess DB. Martin JC. J. Am. Chem. Soc.  1991,  113:  7277 
    CrossrefGoogle Scholar
  • 19 Bonnet B. Soullez D. Girault S. Maes L. Landry V. Davioud-Charvet E. Sergheraert C. Bioorg. Med. Chem.  2000,  8:  95 
    CrossrefGoogle Scholar
17

Dess-Martin periodinane was purchased from Lancaster or Aldrich.