6-methyl-2-[(4-methylphenyl)amino]-4H-3,1-benzoxazin-4-one

• ChemBase ID: 179389
• Molecular Formular: C16H14N2O2
• Molecular Mass: 266.29456
• Monoisotopic Mass: 266.1055277
• SMILES: c1c(ccc2c1c(=O)oc(n2)Nc1ccc(cc1)C)C
• Canonical SMILES: Cc1ccc(cc1)Nc1nc2ccc(cc2c(=O)o1)C
• InChI: 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)
• InChIKey: GFWNGVKCDGYFKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-methyl-2-[(4-methylphenyl)amino]-4H-3,1-benzoxazin-4-one
• IUPAC Traditional name: 6-methyl-2-[(4-methylphenyl)amino]-3,1-benzoxazin-4-one
• Synonyms: 6-Methyl-2-[(4-methylphenyl)amino]-4H-3,1-benzoxazine-4-one; URB754

Database IDs

• CAS Number: 86672-58-4
• PubChem SID: 164235299
• PubChem CID: 848487

CALCULATED PROPERTIES

• Acid pKa: 19.96098
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.437142
• LogD (pH = 7.4): 4.437143
• Log P: 4.437143
• Molar Refractivity: 80.6543 cm^3
• Polarizability: 28.977951 Å^3
• Polar Surface Area: 50.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 201-203°C

DETAILS

Toronto Research Chemicals - U822000

URB754 is a potent, noncompetitive inhibitor of MGL, exhibiting an IC50 of 200 nM for the recombinant rat brain enzyme. It inhibits rat brain fatty acyl amide hydrolase (FAAH) less effectively with an IC50 of 32 μM and binds weakly to the rat CB1 receptor with an IC50 of 3.8 μM. It does not inhibit cyclooxygenase-1 (COX-1) or COX-2 at concentrations up to 100 μM. Inhibition of 2-AG hydrolysis is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.

REFERENCES

• Makara, J.K., et al.: Nat. Neurosci., 8, 1139 (2005)