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URB754
Names
Preferred IUPAC name
6-Methyl-2-(4-methylanilino)-4H -3,1-benzoxazin-4-one
Identifiers
ChemSpider
ECHA InfoCard
100.236.075
UNII
InChI=1S/C16H14N2O2/c1-10-3-6-12(7-4-10)17-16-18-14-8-5-11(2)9-13(14)15(19)20-16/h3-9H,1-2H3,(H,17,18)
N Key: GFWNGVKCDGYFKG-UHFFFAOYSA-N
N InChI=1/C16H14N2O2/c1-10-3-6-12(7-4-10)17-16-18-14-8-5-11(2)9-13(14)15(19)20-16/h3-9H,1-2H3,(H,17,18)
Key: GFWNGVKCDGYFKG-UHFFFAOYAI
CC1=CC=C(C=C1)NC2=NC3=C(C=C(C=C3)C)C(=O)O2
Properties
C 16 H 14 N 2 O 2
Molar mass
266.300 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
URB754 was originally reported by Piomelli et al. to be a potent, noncompetitive
inhibitor of
monoacylglycerol lipase (MGL).
[1] However, recent studies have shown that URB754 failed to inhibit recombinant MGL, and brain
FAAH activity was also resistant to URB754.
[2] In a later study by Piomelli et al. , the MGL-inhibitory activity attributed to URB754 is in fact due to a chemical impurity present in the commercial sample, identified as bis(methylthio)mercurane.
[3]
References
^ Makara JK, Mor M, Fegley D, Szabó SI, Kathuria S, Astarita G, Duranti A, Tontini A, Tarzia G, Rivara S, Freund TF, Piomelli D (2005).
"Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus" . Nat. Neurosci . 8 (9): 1139–41.
doi :
10.1038/nn1521 .
PMID
16116451 .
S2CID
52810445 .
^ Saario SM, Palomäki V, Lehtonen M, Nevalainen T, Järvinen T, Laitinen JT (2006).
"URB754 has no effect on the hydrolysis or signaling capacity of 2-AG in the rat brain" . Chem. Biol . 13 (8): 811–4.
doi :
10.1016/j.chembiol.2006.07.008 .
PMID
16931330 .
^ Tarzia, Giorgio; Antonietti, Francesca; Duranti, Andrea; Tontini, Andrea; Mor, Marco; Rivara, Silvia; Traldi, Pietro; Astarita, Giuseppe; King, Alvin; Clapper, Jason R.; Piomelli, Daniele (2007).
"Identification of a Bioactive Impurity in a Commercial Sample of 6-Methyl-2-p-Tolylaminobenzo[d][1,3]Oxazin-4-One (URB754)" . Annali di Chimica . 97 (9): 887–94.
doi :
10.1002/adic.200790073 .
PMID
17970304 .