1-(4-fluorophenyl)-4-[4-(2-sulfanylidene-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]butan-1-one

• ChemBase ID: 178653
• Molecular Formular: C22H24FN3OS
• Molecular Mass: 397.5088632
• Monoisotopic Mass: 397.16241162
• SMILES: c1cc(ccc1C(=O)CCCN1CCC(CC1)n1c2c([nH]c1=S)cccc2)F
• Canonical SMILES: Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)n1c(=S)[nH]c2c1cccc2
• InChI: InChI=1S/C22H24FN3OS/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28)
• InChIKey: YDLQKLWVKKFPII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-fluorophenyl)-4-[4-(2-sulfanylidene-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]butan-1-one
• IUPAC Traditional name: timiperone
• Synonyms: 4-[4-(2,3-Dihydro-2-thioxo-1H-benzimidazol-1-yl)-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone; 1-[1-[3-(4-Fluorobenzoyl)propyl]-4-piperidyl]-2-mercaptobenzimidazole; 4-Fluoro-4-[4-(2-thioxo-1-benzimidazolinyl)piperidino]butyrophenone; Tolopelon; Timiperone; 4-(4-(2,3-dihydro-2-thioxo-1h-benzimidazol-1-yl)-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone

Database IDs

• CAS Number: 57648-21-2
• PubChem SID: 164234563
• PubChem CID: 3033151

CALCULATED PROPERTIES

• Acid pKa: 8.342014
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.166887
• LogD (pH = 7.4): 3.6814156
• Log P: 3.7489703
• Molar Refractivity: 116.1252 cm^3
• Polarizability: 43.8079 Å^3
• Polar Surface Area: 35.58 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Light Tan Solid
• Melting Point: 198-205°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 97%

DETAILS

Toronto Research Chemicals - T443110

Butyrophenone derivative having neuroleptic activity, used as an antipsychotic.

REFERENCES

• Shimoda, K., et al.: Pharmacol. Toxicol., 83, 164 (1998)
• Sekine, Y., et al.: Eur. J. Clin. Pharmacol., 55, 583 (1998)
• Oka, T., et al.: Life Sci., 76, 225 (1998)
• Fujikawa, M., et al.: Prog. Neuro-Psychopharmacol. Biol. Psych., 32, 755 (1998)