2-hydroxy-2-(1-methylpiperidin-4-yl)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,11,13-pentaen-8-one

• ChemBase ID: 170687
• Molecular Formular: C19H21NO2S
• Molecular Mass: 327.44054
• Monoisotopic Mass: 327.12929992
• SMILES: c12c(C(c3c(C(=O)C1)scc3)(C1CCN(CC1)C)O)cccc2
• Canonical SMILES: CN1CCC(CC1)C1(O)c2ccccc2CC(=O)c2c1ccs2
• InChI: InChI=1S/C19H21NO2S/c1-20-9-6-14(7-10-20)19(22)15-5-3-2-4-13(15)12-17(21)18-16(19)8-11-23-18/h2-5,8,11,14,22H,6-7,9-10,12H2,1H3
• InChIKey: LZPRFURMCOCGDP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2-(1-methylpiperidin-4-yl)-6-thiatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),4,11,13-pentaen-8-one
• IUPAC Traditional name: 2-hydroxy-2-(1-methylpiperidin-4-yl)-6-thiatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),4,11,13-pentaen-8-one
• Synonyms: 4,9-Dihydro-4-hydroxy-4-(1-methyl-4-piperidinyl)-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one; (+/-)-4,9-Dihydro-4-hydroxy-4-(1-methyl-4-piperidinyl)-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one; 4-Hydroxy Ketotifen

Database IDs

• CAS Number: 126939-27-3
• PubChem SID: 164226597
• PubChem CID: 12274855

CALCULATED PROPERTIES

• Acid pKa: 12.071338
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.41099474
• LogD (pH = 7.4): 2.1168752
• Log P: 2.5942152
• Molar Refractivity: 93.473 cm^3
• Polarizability: 35.886814 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943680

Ketotifen (K315100) impurity. Also, an intermediate in the synthesis of the 2-bromo derivative of Ketotifen.

REFERENCES

• Dunn, J.P., et al.: J. Med. Chem., 24, 1097 (1981)
• O’Duffy, J.D., et al.: Drugs, 27, 373 (1981)