URB754

Last updated
URB754
URB754.svg
Names
Preferred IUPAC name
6-Methyl-2-(4-methylanilino)-4H-3,1-benzoxazin-4-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.236.075 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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) X mark.svgN
    Key: GFWNGVKCDGYFKG-UHFFFAOYSA-N X mark.svgN
  • 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
C16H14N2O2
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).
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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

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.


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