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4-Nonylphenylboronic acid

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Chemical compound
Pharmaceutical compound
4-Nonylphenylboronic acid
Clinical data
ATC code
  • None
Identifiers
  • 4-Nonylphenylboronic acid
CAS Number
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Chemical and physical data
FormulaC15H25BO2
Molar mass248.17 g·mol−1
3D model (JSmol)
  • CCCCCCCCCc1ccc(B(O)O)cc1
  • InChI=1S/C15H25BO2/c1-2-3-4-5-6-7-8-9-14-10-12-15(13-11-14)16(17)18/h10-13,17-18H,2-9H2,1H3
  • Key:VONVJOGSLHAKOX-UHFFFAOYSA-N

4-Nonylphenylboronic acid is a potent and selective inhibitor of the enzymefatty acid amide hydrolase (FAAH), with an IC50 of 9.1nM, and 870x selectivity for FAAH over the related enzymeMAGL, which it inhibits with an IC50 of 7900nM.[1] It is also a weaker inhibitor of the enzymesendothelial lipase andlipoprotein lipase, withIC50 values of 100 nM and 1400 nM respectively.[2]

See also

[edit]

References

[edit]
  1. ^Minkkilä A, Saario SM, Käsnänen H, Leppänen J, Poso A, Nevalainen T (November 2008). "Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase".Journal of Medicinal Chemistry.51 (22):7057–60.doi:10.1021/jm801051t.PMID 18983140.
  2. ^O'Connell DP, LeBlanc DF, Cromley D, Billheimer J, Rader DJ, Bachovchin WW (February 2012). "Design and synthesis of boronic acid inhibitors of endothelial lipase".Bioorganic & Medicinal Chemistry Letters.22 (3):1397–401.doi:10.1016/j.bmcl.2011.12.043.PMID 22225633.
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