5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide

• ChemBase ID: 154577
• Molecular Formular: C19H16ClNO4
• Molecular Mass: 357.78764
• Monoisotopic Mass: 357.07678568
• SMILES: COc1cc(cc(c1)OC)NC(=O)c1ccc(o1)c1ccc(cc1)Cl
• Canonical SMILES: COc1cc(cc(c1)OC)NC(=O)c1ccc(o1)c1ccc(cc1)Cl
• InChI: InChI=1S/C19H16ClNO4/c1-23-15-9-14(10-16(11-15)24-2)21-19(22)18-8-7-17(25-18)12-3-5-13(20)6-4-12/h3-11H,1-2H3,(H,21,22)
• InChIKey: VHKBTPQDHDSBSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide
• IUPAC Traditional name: 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide
• Synonyms: 1-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic Acid-13C,d7; 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic Acid-13C,d7; 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic Acid-13C,d7; 5-4(-Chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide; A-803467; A-803467

Database IDs

• CAS Number: 944261-79-4
• MDL Number: MFCD10574689
• PubChem SID: 162248715
• PubChem CID: 16038374

CALCULATED PROPERTIES

• Acid pKa: 11.225808
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.9813051
• LogD (pH = 7.4): 3.9812443
• Log P: 3.9813058
• Molar Refractivity: 96.7273 cm^3
• Polarizability: 37.66245 Å^3
• Polar Surface Area: 60.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Pharmacology Properties

• Target: Sodium Channel

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C19H16NO4Cl

DETAILS

Sigma Aldrich - A3109

Biochem/physiol Actions
A-803467 is a selective Nav1.8 sodium channel blocker and analgesic. A-803467 blocks Nav1.8 with an IC50 of 8 nM and is over 100-fold more selective vs. human Nav1.2, 1.3, 1.5 and 1.7.

Toronto Research Chemicals - C377832

Labelled 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic Acid is used in the preparation of biarylpyrazole based derivatives as cannabinoid CB1 receptor antagonists. It is labelled metabolite M9 of Rimonabant (R517802), an antiobes

REFERENCES

• Kang, S.Y. et al.: Bioorg. Med. Chem. Lett., 18, 2385 (2008)
• Fulp, A. et al.: Bioorg. Med. Chem. Lett., 21, 5711 (2008)
• Bergstrom, M.A. et al., Drug Metabolism and Disposition 39, 1823 (2011).