2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid

• ChemBase ID: 172297
• Molecular Formular: C23H22ClNO2
• Molecular Mass: 379.87928
• Monoisotopic Mass: 379.13390663
• SMILES: c12n(c(c(c1c1ccccc1)c1ccc(cc1)Cl)CC(=O)O)CC(C2)(C)C
• Canonical SMILES: OC(=O)Cc1c(c2ccc(cc2)Cl)c(c2n1CC(C2)(C)C)c1ccccc1
• InChI: InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
• InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
• IUPAC Traditional name: licofelone
• Synonyms: 6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic Acid; ML-3000; Licofelone

Database IDs

• CAS Number: 156897-06-2
• PubChem SID: 164228207
• PubChem CID: 133021

CALCULATED PROPERTIES

• Acid pKa: 4.8260584
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.967785
• LogD (pH = 7.4): 3.1951063
• Log P: 5.7245755
• Molar Refractivity: 108.7876 cm^3
• Polarizability: 44.34479 Å^3
• Polar Surface Area: 42.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 166-169°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: COX

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - L397730

Dual inhibitor of cyclooxygenase and 5-lipoxygenase. Anti-inflammatory.

REFERENCES

• Laufer, S.A., et al.: J. Med. Chem., 37, 1894 (1994)
• Tries, S., et al.: Inflamm. Res., 51, 135 (1994)
• Moreau, M., et al.: J. Vet. Pharmacol. Ther., 28, 81 (1994)