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Volumn 9, Issue 4, 1999, Pages 529-532

Synthesis and biological evaluation of α,α-difluorobenzylphosphonic acid derivatives as small molecular inhibitors of protein-tyrosine phosphatase 1B

Author keywords

Enzyme inhibitors; Isosteres; Mimetics; Phosphonic acids and derivs; Substituent effects

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR;

EID: 0033593914     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00027-X     Document Type: Article
Times cited : (44)

References (34)
  • 7
  • 16
    • 0029921630 scopus 로고    scopus 로고
    • and references cited therein
    • 6. An example of non-peptidyl PTP-inhibitor having aromatic phosphate: Montserat, J.; Chen, L.; Lawrence, D. S.; Zhang, Z-Y. J. Biol. Chem. 1996, 271, 7868 and references cited therein.
    • (1996) J. Biol. Chem. , vol.271 , pp. 7868
    • Montserat, J.1    Chen, L.2    Lawrence, D.S.3    Zhang, Z.-Y.4
  • 24
    • 0013609023 scopus 로고    scopus 로고
    • note
    • 31P-NMR, IR and MS analyses.
  • 28
    • 0013623569 scopus 로고    scopus 로고
    • note
    • 4 was necessary to induce good yield.
  • 29
    • 0013601720 scopus 로고    scopus 로고
    • Deprotection of vinyl derivative 14a under the conditions was problematic due to a concomitant hydrobromination of the vinyl moiety with hydrogen bromide produced during the de-silylation. While the undesired hydrobromination of the ethynyl moiety of 15d and 19d was also observed to some extent on standing the crude acids, this was suppressed by converting the free acids to the corresponding ammonium salts immediately
    • 15. Deprotection of vinyl derivative 14a under the conditions was problematic due to a concomitant hydrobromination of the vinyl moiety with hydrogen bromide produced during the de-silylation. While the undesired hydrobromination of the ethynyl moiety of 15d and 19d was also observed to some extent on standing the crude acids, this was suppressed by converting the free acids to the corresponding ammonium salts immediately.
  • 30
    • 0013626388 scopus 로고    scopus 로고
    • note
    • 50 values were determined as the concentrations of compounds that give a 50% of the control enzyme activity. Briefly, experiments were carried out in triplicate at 5 to 8 different inhibitor concentrations. The inhibitor concentrations were plotted as y-axis and the remaining activity (%) as x-axis, and the concentration of inhibitor that give a 50% inhibition was calculated, using the curve-fit equation (CA-Cricket Graph III).
  • 33
    • 0013581383 scopus 로고    scopus 로고
    • note
    • 2, CuBr in aq. HBr) and Curtius rearrangement (DPPA in refluxing tert-BuOH) in 75% yield for the two-steps.
  • 34
    • 0013580328 scopus 로고    scopus 로고
    • note
    • 19. Prepared from N-Boc-3-iodoaniline by a similar reaction sequence.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.