(1r,4r)-4-[4-(4-fluorophenyl)-5-(2-methoxypyrimidin-4-yl)-1H-imidazol-1-yl]cyclohexan-1-ol

• ChemBase ID: 154181
• Molecular Formular: C20H21FN4O2
• Molecular Mass: 368.4047432
• Monoisotopic Mass: 368.16485415
• SMILES: COc1nc(ccn1)c1n(cnc1c1ccc(cc1)F)[C@H]1CC[C@@H](CC1)O
• Canonical SMILES: COc1nccc(n1)c1c(ncn1[C@@H]1CC[C@H](CC1)O)c1ccc(cc1)F
• InChI: InChI=1S/C20H21FN4O2/c1-27-20-22-11-10-17(24-20)19-18(13-2-4-14(21)5-3-13)23-12-25(19)15-6-8-16(26)9-7-15/h2-5,10-12,15-16,26H,6-9H2,1H3/t15-,16-
• InChIKey: ZQUSFAUAYSEREK-WKILWMFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1r,4r)-4-[4-(4-fluorophenyl)-5-(2-methoxypyrimidin-4-yl)-1H-imidazol-1-yl]cyclohexan-1-ol
• IUPAC Traditional name: (1r,4r)-4-[4-(4-fluorophenyl)-5-(2-methoxypyrimidin-4-yl)imidazol-1-yl]cyclohexan-1-ol
• Synonyms: trans-1-(4-Hydroxycyclohexyl)-4-(4-fluorophenyl)-5-(2-methoxypyridimidin-4-yl)imidazole; SB 239063; trans-4-[4-(4-Fluorophenyl)-5-(2-methoxy-4-pyrimidinyl)-1H-imidazol-1-yl]cyclohexanol; SB 239063

Database IDs

• CAS Number: 193551-21-2
• MDL Number: MFCD03792786
• PubChem SID: 162248320
• PubChem CID: 5166

CALCULATED PROPERTIES

• Acid pKa: 15.255494
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.1579025
• LogD (pH = 7.4): 3.2166483
• Log P: 3.2174628
• Molar Refractivity: 99.289 cm^3
• Polarizability: 40.28516 Å^3
• Polar Surface Area: 73.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble11 mg/mL; H2O: insoluble
• Apperance: white
• Melting Point: 206-207.2 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C20H21N4O2F

DETAILS

Sigma Aldrich - S0569

Biochem/physiol Actions
Potent p38 MAP kinase inhibitor. Selective for α and β. No activity against γ and δ isoforms.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline

Toronto Research Chemicals - S154625

SB239063 is neuroprotective, decreases the number of activated microglia and facilitates neurogenesis in oxygen-glucose-deprived hippocampal slice cultures. A protein kinase inhibitor.

REFERENCES

• Underwood, D., et al.: J. Pharmacol. Exp. Ther., 293, 281 (2000)
• Takahashi, K., et al.: J. Exp. Med., 201, 647 (2000)
• Liu, Z., et al.: Stroke, 38, 146 (2000)