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

Shinya Harusawa; Makoto Kawamura; Shuji Koyabu; Tomoko Hosokawa; Lisa Araki; Yasuhiko Sakamoto; Takeshi Hashimoto; Yumiko Yamamoto; Atsushi Yamatodani; Takushi Kurihara

doi:10.1055/s-2003-42442

PAPER

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

Shinya Harusawa^a, Makoto Kawamura^a, Shuji Koyabu^a, Tomoko Hosokawa^a, Lisa Araki^a, Yasuhiko Sakamoto^b, Takeshi Hashimoto^c, Yumiko Yamamoto^c, Atsushi Yamatodani^c, 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;

Abstract

All articles of this category

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

Full Text

References

1 Grimmett MR. In Comprehensive Heterocyclic Chemistry II: Imidazoles Vol. 3: Katritzky AR. Rees CW. Scriven EF. Pergamon; Oxford: 1996. p.77-220

For reviews, see:

2a Stark H. Schlicker E. Schunack W. Drugs Future 1996, 21: 507

2b Leurs R. Blandian P. Tedford C. Timmerman H. TIPS 1998, 19: 177

2c Watanabe T. Timmerman H. Yanai K. Histamine Reseach in the New Millennium Elsevier; Amsterdom: 2001.

3 For a review, see: Hough LB. Mol. Pharmacol. 2001, 59: 415

4a Harusawa S. Imazu T. Takashima S. Araki L. Ohishi H. Kurihara T. Yamamoto Y. Yamatodani A. Tetrahedron Lett. 1999, 40: 2561

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

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

6a Vollinga RC. Menge WMPB. Leurs R. Timmerman H. J. Med. Chem. 1995, 38: 266

6b Vollinga RC. Menge WMPB. Leurs R. Timmerman H. J. Med. Chem. 1995, 38: 2244

6c De Esch IJP. Gaffar A. Menge WMPB. Timmerman H. Bioorg. Med. Chem. 1999, 7: 3003

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

7 Harusawa S. Koyabu S. Inoue Y. Sakamoto Y. Araki L. Kurihara T. Synthesis 2002, 1072

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

9b Harusawa S. Murai Y. Moriyama H. Imazu T. Ohishi H. Yoneda R. Kurihara T. J. Org. Chem. 1996, 61: 4405

10a Coates IH, Charles NP, and William OA. inventors; Eur. Pat. Appl., EP 306323.

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

11a Zbiral E. Hugl E. Phosphorus 1972, 2: 29

11b Zbiral E. Synthesis 1974, 775

11c Webb RL. Lewis JJ. J. Heterocycl. Chem. 1981, 18: 1301

12a Staab HA. Datta AP. Angew. Chem., Int. Ed. Engl. 1964, 3: 132

12b Devos A. Remion J. Frisque-Hesbain AM. Colens A. Ghosez L. J. Chem. Soc., Chem. Commun. 1979, 1180

12c Villeneuve GB. Chan TH. Tetrahedron Lett. 1997, 38: 6489

13 Chaturvedi N. Goodman M. Bowers C. Int. J. Peptide Protein Res. 1981, 17: 72

14 Huckin SN. Weiler L. J. Am. Chem. Soc. 1974, 96: 1082

15a Vollinger RC. Zuiderveld OP. Scheerens H. Bast A. Timmerman H. Methods Find Exp. Clin. Pharmacol. 1992, 14: 747

15b Hashimoto T. Hidaka R. Yamamoto Y. Harusawa S. Araki L. Kurihara T. Sakamoto Y. Yamatodani A. Inflamm. Res. 2003, in press

16 Koert U. Stein M. Wagner H. Liebings Ann. 1995, 1415

17

Dess-Martin periodinane was purchased from Lancaster or Aldrich.

18a Frigerio M. Santagostino M. Sputore S. Palmisano G. J. Org. Chem. 1995, 60: 7272

18b Frigerio M. Santagostino M. Tetrahedron. Lett. 1994, 35: 8019

18c Dess DB. Martin JC. J. Am. Chem. Soc. 1991, 113: 7277

19 Bonnet B. Soullez D. Girault S. Maes L. Landry V. Davioud-Charvet E. Sergheraert C. Bioorg. Med. Chem. 2000, 8: 95