Synthetic Studies of Imidazole C-Nucleoside Derivatives: Their Application to Histamine H3- and H4-Ligands

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 61, Issue 7, 2003, Pages 682-693

  Harusawa, Shinya ^a   Araki, Lisa ^b   Kurihara, Takushi ^b  

^a OSAKA MEDICAL COLLEGE   (Japan)

^b NONE

Author keywords

Agonist; C nucleoside; Diazafulvene; H 4 receptor; H3 receptor; Histamine; Imidazole; Mitsunobu reaction; Phenylseleno group; Tetrahydrofuran

Indexed keywords

AMINES; DERIVATIVES; MOLECULES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

LIGANDS;

NUCLEIC ACIDS;

EID: 0141528473     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.61.682     Document Type: Review

References (51)

1. (a) K. A. Watanabe, The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides, L. B. Townsend, Ed., Plenum Press, New York, 1994, Vol. 3, p 421
2. (b) D. E. Levy, C. Tang, The Chemistry of C-Glycosides, Pergamon Press, Oxford, 1995
3. M. R. Grimmett, Comprehensive Heterocyclic Chemistry II: Imidazoles, Vol. 3, A. R. Katritzky, C. W. Rees, E. F. Scriven, Eds., Pergamon Press, Oxford, 1996
4. M. S. Poonian, E. F. Nowoswiat, J. Org. Chem., 45, 203 (1980)
5. D. E. Bergstrom, P. Zhang, J. Zhou, J. Chem. Soc., Perkin Trans. 1, 1994, 3029
6. R. W. Brimblecombe, W. A. M. Duncan, G. J. Durant, J. C. Emmett, C. R. Ganellin, M. E. Parsons, J. Int. Med. Res., 3, 86 (1975)
7. (a) R. C. Mitchell, J. Chem. Soc., Perkin Trans. 2, 1980, 915;
8. (b) D. J. Oilman, D. F. Jones, K. Oldham, J. M. Wardleworth, Spec. Publ. R. Soc. Chem., 42, 58 (1978)
9. T. Ishida, Y. In, M. Inoue, T. Kurihara, K. Morimoto, K. Morisaka, K. Shibata, Chem. Pharm. Bull., 38. 1803 (1990)
10. S. Harusawa, M. Kawabata, Y. Murai, R. Yoneda, T. Kurihara, Chem. Pharm. Bull., 43, 152 (1995)
11. M. Yokoyama, A. Toyoshima, T. Akiba, H. Togo, Chem. Lett., 1994, 265
12. (a) S. Harusawa, Y. Murai, H. Moriyama, H. Ohishi, R. Yoneda, T. Kurihara, Tetrahedron Lett., 36, 3165 (1995);
13. (b) S. Harusawa, Y. Murai, H. Moriyama, T. Imazu, H. Ohishi, R. Yoneda, T. Kurihara, J. Org. Chem., 61, 4405 (1996)
14. R. I. Ngochindo, J. Chem. Soc., Perkin Trans.-1, 1990, 1645
15. (a) O. Mitsunobu, Synthesis, 1981, 1 ;
16. (b) B. H. Lee, A. Biswas, M. J. Miller, J. Org. Chem., 51, 106 (1986);
17. (c) D. L. Hughes, The Mitsunobu Reaction, Org. React., L. A. Paquette, Ed., John Wiley & Sons, Inc., New York, 1992, Vol. 42, p 335
18. T. Tsunoda, Y. Yamamiya, S. Itô, Tetrahedron Lett., 34, 1639 (1993)
19. T. Tsunoda, J. Otsuka, Y. Yamamiya, S. Itô, Chem. Lett., 1993, 539
20. T. C. Bruice, J. L Herz, J. Am. Chem. Soc., 86, 4109 (1964)
21. S. Harusawa, H. Moriyama, Y. Murai, T. Imazu, H. Ohishi, R. Yoneda, T. Kurihara, H. Hata, Y. Sakamoto, Chem. Pharm. Bull., 45, 53 (1997)
22. (a) W. Schunack, Actual. Chim. Ther., 20, 9 (1993);
23. (b) W. Schunack, H. Stark, Eur. J. Drug Metab. Pharmacokinet., 19, 173 (1994);
24. (c) R. Leurs, R. C. Vollinga, H. Timmerman, Prog. Drug Res., 45, 107 (1995);
25. (d) H. Stark, E. Schlicker, W. Schunack, Drug Future, 21, 507 (1996);
26. (e) R. Leurs, P. Blandina, C. Tedford, H. Timmerman, TiPS, 19, 177 (1998)
27. (a) S. Harusawa, T. Imazu.'S. Takashima, L. Araki, H. Ohishi, T. Kurihara, Y. Yamamoto, A. Yamatodani, Tetrahedron Lett., 40, 2561 (1999);
28. (b) S. Harusawa, T. Imazu, S. Takashima, L. Araki, H. Ohishi, T. Kurihara, Y. Sakamoto, Y. Yamamoto, A. Yamatodani, J. Org. Chem., 64, 8608 (1999)
29. (a) P. I. Nagy, G. J. Durant, W. P. Hoss, D. A. Smith, J. Am. Chem. Soc., 116, 4898 (1994);
30. (b) A. P. Mazurek, G. Z. Karpinska, Naturforsch, 49c, 471 (1994)
31. W. Sippl, H. Stark, H. -D. Höltje, Quant. Struct. -Act. Relat., 14, 121 (1995)
32. S. Harusawa, T. Imazu, S. Takashima, L. Araki, H. Ohishi, T. Kurihara, Y. Sakamoto, Y. Yamamoto, A. Yamatodani, In Histamine Research in the New Millennium, T. Watanabe, H. Timmerman, K. Yanai, Eds., Elsevier, Amsterdam, 2001, p 83
33. T. Mochizuki, A. Yamatodani, K. Okakura, M. Takemura, N. Inagaki, H. Wada, Naunyn Schmiedebergs Arch. Pharmacol., 343, 190 (1991)
34. Y. Yamamoto, T. Mochizuki, K. Okakura-Mochizuki, A. Uno, A. Yamatodani, Meth. Find. Exp. Clin. Pharmacol., 19, 289 (1997)
35. T. Hashimoto, S. Harusawa, L. Araki, O. P. Zuiderveld, M. J. Smit, T. Imazu, S. Takashima, Y. Yamamoto, Y. Sakamoto, T. Kurihara, R. Leurs, R. A. Bakker, A. Yamatodani, J. Med. Chem., in press (JM 0300025)
36. (a) C. Liu, X. J. Ma, X. Jiang, S. J. Wilson, C. L. Hofstra, J. Blevitt, J. Pyati, X. Li, W. Chai, N. Carruthers, T. W. Lovenberg, Mol. Pharmacol., 59, 420 (2001);
37. (b) T. Nakamura, H. Itadani, Y. Hidaka, M. Ohta, K. Tanaka, Biochem. Biophys. Res. Commum., 279, 615 (2000);
38. (c) K. L. Morse, J. Behan, T. M. Laz, R. E. West, S. A. Greefeder, J. C. Anthes, S. Umland, Y. Wan, R. W. Hipkin, W. Gonsiorek, N. Shin, E. L. Gustafson, X. Qiao, S. Wang, J. A. Hendrick, J. Greene, M. Bayne, F. J. Monsma, J. Pharmacol. Exp. Ther., 296, 1058 (2001);
39. (d) Y. Zhu, D. Michalovich, H. L. Wu, K. B. Tan, G. M. Dycko, I. J. Mannan, R. Boyce, J. Alston, L. A. Tierney, X. Li, N. C. Herrity, L. Vawter, H. M. Sarau, R. S. Ames, C. M. Davenport, J. P. Hieble, S. Wilson, D. J. Bergsma, L. R. Fitzgerald, Mol. Pharmacol., 59, 434 (2001);
40. (e) T. Nguyen, D. A. Shapiro, S. R. George, V. Setola, D. K. Lee, R. Cheng, L. Rauser, S. P. Lee, K. R. Lynch, B. L. Roth, B. F. O'Dowd, Mol. Pharmacol., 59, 427 (2001);
41. (f) T. Oda, N. Morikawa, Y. Saito, Y. Masuho, S. Matsumoto, J. Biol. Chem., 275, 36781 (2000)
42. For a review, see L. B. Hough, Mol. Pharmacol., 59, 415 (2001)
43. (a) S. Harusawa, L. Araki, H. Terashima, M. Kawamura, S. Takashima, Y. Sakamoto, T. Hashimoto, Y. Yamamoto, A. Yamatodani, T. Kurihara, Chem. Pharm. Bull., in press;
44. (b) S. Harusawa, L. Araki, T. Imazu, H. Ohishi, Y. Sakamoto, T. Kurihara, ibid., 51, 325 (2003)
45. L. Araki, S. Harusawa, H. Suzuki, T. Kurihara, Heterocycles, 53, 1957 (2000)
46. L. Araki, S. Harusawa, M. Fukuda, T. Kurihara, Heterocycles, 55, 1907 (2001)
47. S. Harusawa, I. Ijichi, L. Araki, T. Kurihara, Heterocycles, 53, 2739 (2000)
48. L. Araki, S. Harusawa, I. Ijichi, H. Ohishi, T. Kurihara, Heterocycles, 55, 889 (2001)
49. (a) D. Guianvarc'h, R. Benhida, J. -L. Fourrey, Tetrahedron Lett., 42, 647 (2001);
50. (b) D. Guianvarc'h, J. -L. Fourrey, M. -E. T. H. Dau, V. Guérineau, R. Benhida, J. Org. Chem., 67, 3724 (2002)