7-{4-[(3-phenylphenyl)methyl]piperazin-1-yl}-2,3-dihydro-1,3-benzoxazol-2-one; methanesulfonic acid

• ChemBase ID: 161978
• Molecular Formular: C25H27N3O5S
• Molecular Mass: 481.56398
• Monoisotopic Mass: 481.16714198
• SMILES: C1N(CCN(C1)Cc1cccc(c1)c1ccccc1)c1c2c(ccc1)[nH]c(=O)o2.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.O=c1[nH]c2c(o1)c(ccc2)N1CCN(CC1)Cc1cccc(c1)c1ccccc1
• InChI: InChI=1S/C24H23N3O2.CH4O3S/c28-24-25-21-10-5-11-22(23(21)29-24)27-14-12-26(13-15-27)17-18-6-4-9-20(16-18)19-7-2-1-3-8-19;1-5(2,3)4/h1-11,16H,12-15,17H2,(H,25,28);1H3,(H,2,3,4)
• InChIKey: ONWKHSGOYGLGPO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{4-[(3-phenylphenyl)methyl]piperazin-1-yl}-2,3-dihydro-1,3-benzoxazol-2-one; methanesulfonic acid
• IUPAC Traditional name: bifeprunox; methanesulfonic acid
• Synonyms: 7-[4-([1,1'-Biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone Mesylate; Du-127090; Bifeprunox Mesylate

Database IDs

• CAS Number: 350992-13-1
• PubChem SID: 162256113
• PubChem CID: 6918587

CALCULATED PROPERTIES

• Acid pKa: 9.470039
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3429976
• LogD (pH = 7.4): 4.078898
• Log P: 4.507515
• Molar Refractivity: 116.4917 cm^3
• Polarizability: 45.03033 Å^3
• Polar Surface Area: 44.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 257-259°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B383200

Used as an antipsychotic compound. Activates the serotonin 5-hydroxytryptamine (5-HT)1A receptor.

REFERENCES

• Wolf, W., et al.: Curr. Opin. Invest. Drugs, 4, 72 (2003)
• Assie, M.B., et al.: J. Pharmacol. Exp. Ther., 315(2003)
• 265 (2005)