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Volumn 8, Issue 24, 1998, Pages 3683-3688

Alkoxide-catalyzed ring-opening of a novel homosaccharin derivative: Synthesis of potent, selective P3-lactam thrombin inhibitors containing P4- o-alkoxycarbonylbenzylsulfonamide residues

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM DERIVATIVE; OXIDE; PLASMIN; PRODRUG; SACCHARIN DERIVATIVE; THROMBIN; THROMBIN INHIBITOR;

EID: 0032534884     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00667-2     Document Type: Article
Times cited : (17)

References (35)
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    • note
    • 1. Dedicated with great admiration and respect to our illustrious chemistry department consultant, Professor Henry Rapoport, Department of Chemistry, University of California at Berkeley, on the occasion of his 80th birthday.
  • 2
    • 0013590703 scopus 로고    scopus 로고
    • Boston, MA, August 23-27, Medicinal Chemistry Section, MEDI-073
    • 2. Portions of this work were presented at the 216th National American Chemical Society Meeting, Boston, MA, August 23-27, 1998; Medicinal Chemistry Section, MEDI-073.
    • (1998) 216th National American Chemical Society Meeting
  • 3
    • 77956716245 scopus 로고    scopus 로고
    • Bristol, J. A., Ed.; Academic: San Diego
    • 3. Recent Reviews: (a) Vacca, J. P. In Ann. Rep. Med. Chem. Bristol, J. A., Ed.; Academic: San Diego, 1998; Vol. 33, 81.
    • (1998) Ann. Rep. Med. Chem. , vol.33 , pp. 81
    • Vacca, J.P.1
  • 5
    • 0013481920 scopus 로고    scopus 로고
    • Bristol, J. A., Ed.; Academic Press: San Diego
    • (c) Ripka, W. C.; Vlasuk G. P. In Ann. Rep. Med. Chem. Bristol, J. A., Ed.; Academic Press: San Diego, 1997; Vol. 32, 71.
    • (1997) Ann. Rep. Med. Chem. , vol.32 , pp. 71
    • Ripka, W.C.1    Vlasuk, G.P.2
  • 7
    • 0030693694 scopus 로고    scopus 로고
    • Expert Opin. Ther. Pat. 1997, 7 , 1265
    • (e) Wiley, M. R. ; Fisher, M. J. Expert Opin. Ther. Pat. 1997, 7 , 1265.
    • Wiley, M.R.1    Fisher, M.J.2
  • 26
    • 0345107311 scopus 로고
    • 5-mediated intramolecular dehydration using rather vigorous conditions as well as the strong protic acid or base hydrolytic ring-opening reactions under drastic conditions have been described. See (a) Sianesi, E.; Redaelli, R.; Magistretti, M. J.; Massarani, E. J. Med. Chem. 1973, 16, 1122.
    • (1973) J. Med. Chem. , vol.16 , pp. 1122
    • Sianesi, E.1    Redaelli, R.2    Magistretti, M.J.3    Massarani, E.4
  • 27
    • 0014729392 scopus 로고
    • JES acknowledges a reviewer for providing the following precedents of alkoxide-catalyzed ring-opening of saccharin derivatives, see
    • (b) Sianesi, E.; Redaelli, R.; Bertani, M.; Da Re, P. Chem. Ber. 1970, 103, 1992. JES acknowledges a reviewer for providing the following precedents of alkoxide-catalyzed ring-opening of saccharin derivatives, see:
    • (1970) Chem. Ber. , vol.103 , pp. 1992
    • Sianesi, E.1    Redaelli, R.2    Bertani, M.3    Da Re, P.4
  • 30
    • 0345538723 scopus 로고    scopus 로고
    • note
    • 12. All new compounds were characterized by full spectroscopic (NMR, low/high resolution MS) data. Yields refer to spectroscopically and chromatographically homogenous (≥95% by HPLC, TLC) materials.
  • 32
    • 0344244947 scopus 로고    scopus 로고
    • note
    • 14. The in vitro enzyme assays were performed according to the protocols described in refs 3 and 4.


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