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Romero, F. Anthony; Du, Wu; Hwang, Inkyu; Rayl, Thomas J; Kimball, F. Scott; Leung, Donmienne; Hoover, Heather S; Apodaca, Richard L; Breitenbucher, J. Guy; Cravatt, Benjamin F; Boger, Dale L
Journal of medicinal chemistry, 03/2007, Volume: 50, Issue: 5Journal Article
A study of the structure−activity relationships (SAR) of 2f (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed, targeting the 5-position of the oxazole. Examination of a series of substituted benzene derivatives (12 − 14) revealed that the optimal position for substitution was the meta-position with selected members approaching or exceeding the potency of 2f. Concurrent with these studies, the effect of substitution on the pyridine ring of 2f was also examined. A series of small, nonaromatic C5-substituents was also explored and revealed that the K i follows a well-defined correlation with the Hammett σp constant (ρ = 3.01, R 2 = 0.91) in which electron-withdrawing substituents enhance potency, leading to inhibitors with K is as low as 400 pM (20n). Proteomic-wide screening of the inhibitors revealed that most are exquisitely selective for FAAH over all other mammalian proteases, reversing the 100-fold preference of 20a (C5 substituent = H) for the enzyme TGH.
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