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Volumn 18, Issue 4, 2008, Pages 1288-1292

α,β-Cyclic-β-benzamido hydroxamic acids: Novel oxaspiro[4.4]nonane templates for the discovery of potent, selective, orally bioavailable inhibitors of tumor necrosis factor-α converting enzyme (TACE)

Author keywords

Amino acid; Matrix metalloprotease; MMP; TACE; TNF converting enzyme

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; LIPOPOLYSACCHARIDE; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR;

EID: 38949095681     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.030     Document Type: Article
Times cited : (18)

References (20)
  • 10
    • 38949116423 scopus 로고    scopus 로고
    • note
    • 50 = 263 nM).
  • 11
    • 0242626789 scopus 로고    scopus 로고
    • For examples of the preparation of cyclic β-amino acids using a Curtius rearrangement, see:
    • For examples of the preparation of cyclic β-amino acids using a Curtius rearrangement, see:. Bolm C., Schiffers I., Atodiresei I., and Hackenberger C.P.R. Tetrahedron: Asymmetry 14 (2003) 3455
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 3455
    • Bolm, C.1    Schiffers, I.2    Atodiresei, I.3    Hackenberger, C.P.R.4
  • 12
    • 38949147198 scopus 로고    scopus 로고
    • note
    • 1H NMR and low resolution mass spectrometry data.
  • 13
    • 38949201809 scopus 로고    scopus 로고
    • note
    • The numbering system of the oxaspiro[4.4]nonane system is reflected in the structure.
  • 14
    • 0001650729 scopus 로고    scopus 로고
    • The GOESY is a double-PFG-spin-echo, transient nOe experiment using shape selective pulses and pulse field gradients in which the results appear similar to a steady-state nOe difference experiment. Since excitation is done with shaped pulses, a much narrower region of the spectrum is affected so it is possible to see weaker nOes than with a steady-state nOe difference experiment, see
    • The GOESY is a double-PFG-spin-echo, transient nOe experiment using shape selective pulses and pulse field gradients in which the results appear similar to a steady-state nOe difference experiment. Since excitation is done with shaped pulses, a much narrower region of the spectrum is affected so it is possible to see weaker nOes than with a steady-state nOe difference experiment, see. Stott K., Keeler J., Van Q.N., and Shaka A.J. J. Magn. Reson. 125 (1997) 302
    • (1997) J. Magn. Reson. , vol.125 , pp. 302
    • Stott, K.1    Keeler, J.2    Van, Q.N.3    Shaka, A.J.4
  • 15
    • 38949130572 scopus 로고    scopus 로고
    • note
    • The coordinates for 21 have been placed in the Cambridge Crystallographic Data Centre, deposition number: CCDC 670062.
  • 20
    • 38949200395 scopus 로고    scopus 로고
    • note
    • For related analogs in the α,β-cyclic-β-benzamido hydroxamic acid series, replacement of the 4-[(2-methylquinolin-4-yl)methoxy]benzamide P1' substituent with 4-[(2,6-dimethylpyridin-4-yl)methoxy]benzamide resulted in maintenance of pTACE activity but loss in both WBA activity and selectivity against MMPs-2 and -13. Ott, G. R.; Asakawa, N, unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.