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Volumn 46, Issue 38, 2005, Pages 6515-6518

Synthesis of α-trifluoromethyl-α-amino-β-sulfone hydroxamates: Novel nanomolar inhibitors of matrix metalloproteinases

Author keywords

Fluorine; Inhibitors; Matrix metalloproteinases; Sulfones

Indexed keywords

ALPHA TRIFLUOROMETHYL ALPHA AMINO BETA SULFONE HYDROXAMATE; GELATINASE B; INTERSTITIAL COLLAGENASE; MATRIX METALLOPROTEINASE INHIBITOR; PYRUVIC ACID DERIVATIVE; STROMELYSIN; SULFUR; UNCLASSIFIED DRUG;

EID: 23844507616     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.078     Document Type: Article
Times cited : (21)

References (29)
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    • Zanda, M.1
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    • note
    • Several unidentified by-products formed, according to TLC monitoring.
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    • note
    • +] (4), 233 (23), 108 (82), 91 (100).
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    • 33645367842 scopus 로고    scopus 로고
    • note
    • +] (22), 233 (100).
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    • 33645346516 scopus 로고    scopus 로고
    • note
    • The striking difference of reactivity in the saponification reaction between sulfone 9 and sulfides 16 could be due to the difference of acidity of the α-sulfonyl and the α-sulfanyl protons.
  • 23
    • 33645353911 scopus 로고    scopus 로고
    • note
    • These oxidations performed by m-CPBA at rt occurred in modest to fair yields, as a likely consequence of side reactions involving the hydroxamate moiety and/or the electron-rich aryl groups. In fact, several unidentified by-products were detected by TLC monitoring.
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    • Full length MMP-1 was purchased from Biomol, and the activity of 1a measured by collagen gel zymography as previously described (see Ref. 18). The catalytic domains of MMP-3 and MMP-9 enzymes were produced in E. coli, transfected with cDNAs corresponding to the respective human sequences. Proteins were purified by affinity chromatography and the inhibitory potencies of racemic 1 and single enantiomers were assayed with synthetic, general MMP fluorescent substrate (Mca-PLGLDpaAR, Tebu-bio) using a FL600 Avantec fluorimeter. For MMP-3 see: Q.Z. Ye, L.L. Johnson, D.J. Hupe, and V. Baragi Biochemistry 31 1992 11231 11235
    • (1992) Biochemistry , vol.31 , pp. 11231-11235
    • Ye, Q.Z.1    Johnson, L.L.2    Hupe, D.J.3    Baragi, V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.