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1851955 
Journal Article 
alpha-hydroxyketones as inhibitors of urease 
Tanaka, T; Kawase, M; Tani, S 
2004 
Yes 
Bioorganic & Medicinal Chemistry
ISSN: 0968-0896
EISSN: 1464-3391 
Elsevier 
12 
2 
501-505 
English 
14723968 
WOS:000188394700018 
A variety of alpha-hydroxyketones (1-13) and alpha-diketones (14-20) were evaluated for their effect on the jack bean urease. Of 13 alpha-hydroxyketones (1-13) tested, 2,2'-thenoin (10) (IC(50)=0.18 mM), furoin (9) (IC(50)=0.36 mM), 2-hydroxy-1-phenylethanone (5) (IC(50)=0.47 mM) and acetol (1) (IC(50)=2.9 mM) showed potent inhibitory activity against the enzyme, comparable with hydroxyurea (IC(50)=0.1 mM). The inhibitory effects were completely blocked by 2-mercaptoethanol or dithiothreitol. A nickel ion influenced the inhibitory effects of 5 and 9 in a dose-dependent manner, but not of 1 and 10. On the other hand, the corresponding alpha-diketones such as 2,2'-thenil (20), furil (19) and PhCOCHO (14) exhibited little or no ability to inhibit the urease. We have demonstrated for the first time that some alpha-hydroxyketone derivatives show urease inhibitory activity, possibly by binding to cysteinyl residues in the active site. 
urease inhibitor; alpha-hydroxyketone; alpha-diketone; Jack bean urease