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Volumn 40, Issue 13, 1999, Pages 2561-2564

Synthesis of imifuramine and its stereoisomers exhibiting histamine H3- agonistic activity

Author keywords

[No Author keywords available]

Indexed keywords

HISTAMINE AGONIST; IMIDAZOLE DERIVATIVE; IMIFURAMINE; UNCLASSIFIED DRUG;

EID: 0033605932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00202-6     Document Type: Article
Times cited : (29)

References (29)
  • 12
    • 0013632226 scopus 로고
    • Ph. D. Dissertation, Vrije Universiteit Amsterdam
    • (c) Vollinga, R.C. Ph. D. Dissertation, Vrije Universiteit Amsterdam, 1995.
    • (1995)
    • Vollinga, R.C.1
  • 18
    • 0013581936 scopus 로고    scopus 로고
    • note
    • 1′,2′ = 16.2 Hz, 1′-H), 6.86 (s, 1H, 5-H), 7.28 (s, 5H, Ph), 7.49 (s, 1H, 2-H).
  • 19
    • 0013611174 scopus 로고    scopus 로고
    • note
    • Cyclization of 7S did not proceed under refluxing HC1-THF, but only diol having an unsaturated imidazole was obtained.
  • 20
    • 0013609586 scopus 로고    scopus 로고
    • note
    • A solution of 7R (1.32 g, 2.03 mmol) in THF (24 ml) was refluxed with 1.5N HC1 (9 ml) for 1h, and then diluted with benzene (50ml). The resulting mixture was further refluxed to remove water for 1h as an azeotrope using a Dean-Stark water separator. The workup and purification gave 9 (0.35 g, 42%) and 10 (0.46 g, 55%).
  • 21
    • 0013578496 scopus 로고    scopus 로고
    • note
    • It was supported by the fact that a reaction of the 11 with PhSeCl smoothly proceeded to give 9 and 10 in refluxing THF.
  • 22
    • 0013578497 scopus 로고    scopus 로고
    • note
    • Only the 8S was obtained from lactol 5β without the formation of C-1'epimer.
  • 23
    • 0000457348 scopus 로고
    • Townsend, L. B., Ed.; Plenum Press: New York
    • For recent reviews on the chemistry, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Watanabe, K. A. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1994) Chemistry of Nucleosides and Nucleotides , vol.3 , pp. 421-535
    • Watanabe, K.A.1
  • 24
    • 33750865454 scopus 로고    scopus 로고
    • The chemistry of c-nucleosides and their analogs I: C-nucleosides of hetero monocyclic bases
    • Katritzky, A. R. Ed.; Academic Press: New York
    • (b)Shaban, M. A. E.; Nasr, A. Z. The chemistry of c-nucleosides and their analogs I: C-nucleosides of hetero monocyclic bases. In Advances In Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1997; Vol.68, pp 223-432.
    • (1997) Advances in Heterocyclic Chemistry , vol.68 , pp. 223-432
    • Shaban, M.A.E.1    Nasr, A.Z.2
  • 25
    • 0003280647 scopus 로고
    • The chemistry of C-glycosides
    • Baldwin, J.E.; Magnus, P.D., Eds.; Pergamon: New York
    • (c) Levy, D.E.; Tang, C. The chemistry of C-glycosides. In Tetrahedron Organic Chimistry Series; Baldwin, J.E.; Magnus, P.D., Eds.; Pergamon: New York, 1995; Vol. 13.
    • (1995) Tetrahedron Organic Chimistry Series , vol.13
    • Levy, D.E.1    Tang, C.2
  • 27
    • 0013580630 scopus 로고    scopus 로고
    • note
    • 3OD, 1′-H), 7.03 (s, 1H, 4-H), 7.65 (s, 1H, 2-H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.