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Volumn 9, Issue 16, 2007, Pages 3061-3064

Application of ring-closing metathesis for the synthesis of macrocyclic peptidomimetics as inhibitors of HCV NS3 protease

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; PEPTIDE; PYRROLE DERIVATIVE;

EID: 34547948019     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0711265     Document Type: Article
Times cited : (39)

References (31)
  • 1
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    • (a) Cohen, J. Science 1999, 285, 26.
    • (1999) Science , vol.285 , pp. 26
    • Cohen, J.1
  • 5
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    • See the following reviews and references therein: a
    • See the following reviews and references therein: (a) Chen, S. H.; Tan, S. L. Curr. Med. Chem 2005, 12, 2317.
    • (2005) Curr. Med. Chem , vol.12 , pp. 2317
    • Chen, S.H.1    Tan, S.L.2
  • 8
    • 4444345444 scopus 로고    scopus 로고
    • BILN 2061 was the first compound to undergo clinical trials. It is also a macrocyclic inhibitor of HCV NS3 protease. See: (a) Faucher, A. M. et al. Org. Lett. 2004, 6, 2901.
    • BILN 2061 was the first compound to undergo clinical trials. It is also a macrocyclic inhibitor of HCV NS3 protease. See: (a) Faucher, A. M. et al. Org. Lett. 2004, 6, 2901.
  • 14
    • 0035847669 scopus 로고    scopus 로고
    • See the following examples and references therein for SAR of electrophilic serine traps in HCV NS3 inhibitors: (a) Bennett, J. M., et al. Bioorg. Med. Chem. Lett. 2001, 11, 355.
    • See the following examples and references therein for SAR of electrophilic serine traps in HCV NS3 inhibitors: (a) Bennett, J. M., et al. Bioorg. Med. Chem. Lett. 2001, 11, 355.
  • 20
    • 34547939221 scopus 로고    scopus 로고
    • The synthesis of 16-membered macrocycles is shown in the manuscript. See the Supporting Information for synthesis and characterization of 15- and 17-membered macrocycles.
    • The synthesis of 16-membered macrocycles is shown in the manuscript. See the Supporting Information for synthesis and characterization of 15- and 17-membered macrocycles.
  • 21
    • 0032539507 scopus 로고    scopus 로고
    • For preparation of 5a using an alternative approach, see: (a) Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357.
    • For preparation of 5a using an alternative approach, see: (a) Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357.
  • 23
    • 84890757673 scopus 로고    scopus 로고
    • For examples of rhodium-catalyzed asymmetric hydrogenations, see: Chi, Y, Tang, W, Zhang, X. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A, Ed, Wiley-VCH: Weinheim, 2005; pp 1-31
    • For examples of rhodium-catalyzed asymmetric hydrogenations, see: Chi, Y.; Tang, W.; Zhang, X. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; pp 1-31.
  • 27
    • 34547934362 scopus 로고    scopus 로고
    • Allyl isocyanide can be prepared by dehydration of N-allylformamide following the procedure described for the preparation of cyclopropyl isocyanide in: Schöllkopf, U. et al. Liebigs Ann. Chem. 1976, 1, 183.
    • Allyl isocyanide can be prepared by dehydration of N-allylformamide following the procedure described for the preparation of cyclopropyl isocyanide in: Schöllkopf, U. et al. Liebigs Ann. Chem. 1976, 1, 183.
  • 29
    • 34547948318 scopus 로고    scopus 로고
    • The methyl ester analogue of 6b was used in the synthesis of oxygencontaining macrocycles.
    • The methyl ester analogue of 6b was used in the synthesis of oxygencontaining macrocycles.
  • 30
    • 34547937035 scopus 로고    scopus 로고
    • A manuscript describing the synthesis and structure-activity relationship (potency and pharmacokinetic profiles) of macrocyclic inhibitors using this approach is in preparation.
    • A manuscript describing the synthesis and structure-activity relationship (potency and pharmacokinetic profiles) of macrocyclic inhibitors using this approach is in preparation.
  • 31
    • 0023728105 scopus 로고    scopus 로고
    • i* and discussion, see: Morrison, J. F.; Walsh, C. T. Advances in Enzymology and Related Areas of Molecular Biology; Meister, A., Ed.; John Wiley & Sons: Hoboken, NJ, 1988; 61, pp 201.
    • i* and discussion, see: Morrison, J. F.; Walsh, C. T. Advances in Enzymology and Related Areas of Molecular Biology; Meister, A., Ed.; John Wiley & Sons: Hoboken, NJ, 1988; Vol. 61, pp 201.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.