[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methanol

• ChemBase ID: 167162
• Molecular Formular: C14H14Cl2N2O3
• Molecular Mass: 329.17856
• Monoisotopic Mass: 328.03814768
• SMILES: C1O[C@@](O[C@H]1CO)(c1c(cc(cc1)Cl)Cl)Cn1ccnc1
• Canonical SMILES: OC[C@H]1CO[C@](O1)(Cn1cncc1)c1ccc(cc1Cl)Cl
• InChI: InChI=1S/C14H14Cl2N2O3/c15-10-1-2-12(13(16)5-10)14(8-18-4-3-17-9-18)20-7-11(6-19)21-14/h1-5,9,11,19H,6-8H2/t11-,14-/m0/s1
• InChIKey: VJZJGRMLFMJRGG-FZMZJTMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methanol
• IUPAC Traditional name: [(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methanol
• Synonyms: (2R,4S)-rel-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol; cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol

Database IDs

• CAS Number: 61397-58-8
• PubChem SID: 162261295
• PubChem CID: 794639

CALCULATED PROPERTIES

• Acid pKa: 14.595739
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1478605
• LogD (pH = 7.4): 2.6124668
• Log P: 2.6753886
• Molar Refractivity: 79.0574 cm^3
• Polarizability: 30.994545 Å^3
• Polar Surface Area: 56.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: 130-132°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D435930

cis-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol is a Ketoconazole (K186000) fragment that may have modulatory activity on the large conductance calcium-activated potassium channel (BKCa).

REFERENCES

• Power, E.C. et al.: Bioorg. Med. Chem., 16, 887 (2006)
• Heeres, J. et al.: J. Med. Chem., 22, 1003 (2006)