4-Nonylphenylboronic acid: Difference between revisions

4-Nonylphenylboronic acid
Clinical data
ATC code	None;
Identifiers
	IUPAC name 4-Nonylphenylboronic acid;
CAS Number	256383-45-6;
PubChem CID	4589192;
ChemSpider	3781380;
CompTox Dashboard (EPA)	DTXSID10404611 ;
Chemical and physical data
Formula	C15H25BO2
Molar mass	248.17 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCCCc1ccc(B(O)O)cc1;
	InChI 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;

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Latest revision as of 11:39, 23 January 2023

4-Nonylphenylboronic acid is a potent and selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH), with an IC₅₀ of 9.1nM, and 870x selectivity for FAAH over the related enzyme MAGL, which it inhibits with an IC₅₀ of 7900nM.^[1] It is also a weaker inhibitor of the enzymes endothelial lipase and lipoprotein lipase, with IC₅₀ values of 100 nM and 1400 nM respectively.^[2]

References

^ 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.
^ 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.

[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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[2]

@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
 {{Drugbox
 | IUPAC_name               = 4-Nonylphenylboronic acid
-| image                    = 4-Nonylphenylboronicacid_structure.png
+| image                    = 4-Nonylphenylboronic acid Structure.svg
 | width                    = 280
 | CAS_number               = 256383-45-6
@@ Line 11: / Line 12: @@
 | C=15 | H=25 | B=1 | O=2
+| smiles                   = CCCCCCCCCc1ccc(B(O)O)cc1
-| molecular_weight         = 248.17 g/mol
-| smiles                   = OB(O)C1=CC=C(CCCCCCCCC)C=C1
-| InChI             = 1/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
-| InChIKey          = VONVJOGSLHAKOX-UHFFFAOYAY
 | StdInChI          = 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
 | StdInChIKey       = VONVJOGSLHAKOX-UHFFFAOYSA-N
@@ Line 27: / Line 25: @@
 }}
-'''4-Nonylphenylboronic acid''' is a potent and selective inhibitor of the enzyme [[fatty acid amide hydrolase]] (FAAH), with an IC<sub>50</sub> of 9.1nM, and 870x selectivity for FAAH over the related enzyme [[Monoacylglycerol lipase|MAGL]], which it inhibits with an IC<sub>50</sub> of 7900nM.<ref>{{Cite journal | last1 = Minkkilä | first1 = A. | last2 = Saario | first2 = S. M. | last3 = Käsnänen | first3 = H. | last4 = Leppänen | first4 = J. | last5 = Poso | first5 = A. | last6 = Nevalainen | first6 = T. | doi = 10.1021/jm801051t | title = Discovery of Boronic Acids as Novel and Potent Inhibitors of Fatty Acid Amide Hydrolase | journal = Journal of Medicinal Chemistry | volume = 51 | issue = 22 | pages = 7057–7060 | year = 2008 | pmid =  18983140| pmc = }}</ref> It is also a weaker inhibitor of the enzymes [[endothelial lipase]] and [[lipoprotein lipase]], with IC<sub>50</sub> values of 100nM and 1400nM respectively.<ref>{{Cite journal | last1 = o’Connell | first1 = D. P. | last2 = Leblanc | first2 = D. F. | last3 = Cromley | first3 = D. | last4 = Billheimer | first4 = J. | last5 = Rader | first5 = D. J. | last6 = Bachovchin | first6 = W. W. | doi = 10.1016/j.bmcl.2011.12.043 | title = Design and synthesis of boronic acid inhibitors of endothelial lipase | journal = Bioorganic & Medicinal Chemistry Letters | volume = 22 | issue = 3 | pages = 1397 | year = 2012 | pmid =  | pmc = }}</ref>
+'''4-Nonylphenylboronic acid''' is a potent and selective inhibitor of the enzyme [[fatty acid amide hydrolase]] (FAAH), with an IC<sub>50</sub> of 9.1nM, and 870x selectivity for FAAH over the related enzyme [[Monoacylglycerol lipase|MAGL]], which it inhibits with an IC<sub>50</sub> of 7900nM.<ref>{{cite journal | vauthors = Minkkilä A, Saario SM, Käsnänen H, Leppänen J, Poso A, Nevalainen T | title = Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase | journal = Journal of Medicinal Chemistry | volume = 51 | issue = 22 | pages = 7057–60 | date = November 2008 | pmid = 18983140 | doi = 10.1021/jm801051t }}</ref> It is also a weaker inhibitor of the enzymes [[endothelial lipase]] and [[lipoprotein lipase]], with {{IC50}} values of 100&nbsp;nM and 1400&nbsp;nM respectively.<ref>{{cite journal | vauthors = O'Connell DP, LeBlanc DF, Cromley D, Billheimer J, Rader DJ, Bachovchin WW | title = Design and synthesis of boronic acid inhibitors of endothelial lipase | journal = Bioorganic & Medicinal Chemistry Letters | volume = 22 | issue = 3 | pages = 1397–401 | date = February 2012 | pmid = 22225633 | doi = 10.1016/j.bmcl.2011.12.043 }}</ref>
-==See also==
+== See also ==
 * [[IDFP]]
 * [[LY-2183240]]
 * [[URB-597]]
-==References==
+== References ==
 {{reflist}}
 {{Cannabinoids}}
 {{DEFAULTSORT:Nonylphenylboronic acid, 4-}}