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Benzothiophene piperazine and piperidine urea inhibitors of fatty acid amide hydrolase (FAAH).
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2009 May 15; Vol. 19 (10), pp. 2865-9. Date of Electronic Publication: 2009 Mar 24. - Publication Year :
- 2009
-
Abstract
- The synthesis and structure-activity relationships (SAR) of a series of benzothiophene piperazine and piperidine urea FAAH inhibitors is described. These compounds inhibit FAAH by covalently modifying the enzyme's active site serine nucleophile. Activity-based protein profiling (ABPP) revealed that these urea inhibitors were completely selective for FAAH relative to other mammalian serine hydrolases. Several compounds showed in vivo activity in a rat complete Freund's adjuvant (CFA) model of inflammatory pain.
- Subjects :
- Amidohydrolases metabolism
Animals
Computer Simulation
Enzyme Inhibitors chemistry
Enzyme Inhibitors pharmacology
Humans
Models, Chemical
Piperazines chemical synthesis
Piperazines pharmacology
Piperidines chemical synthesis
Piperidines pharmacology
Rats
Structure-Activity Relationship
Thiophenes chemical synthesis
Thiophenes pharmacology
Urea chemical synthesis
Urea pharmacology
Amidohydrolases antagonists & inhibitors
Enzyme Inhibitors chemical synthesis
Piperazines chemistry
Piperidines chemistry
Thiophenes chemistry
Urea analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 19
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 19386497
- Full Text :
- https://doi.org/10.1016/j.bmcl.2009.03.080