4-[(E)-[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanamide

• ChemBase ID: 176930
• Molecular Formular: C17H16ClFN2O2
• Molecular Mass: 334.7725432
• Monoisotopic Mass: 334.08843366
• SMILES: c1cc(cc(c1O)/C(=N/CCCC(=O)N)/c1ccc(cc1)Cl)F
• Canonical SMILES: NC(=O)CCC/N=C(/c1cc(F)ccc1O)\c1ccc(cc1)Cl
• InChI: InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,22H,1-2,9H2,(H2,20,23)/b21-17+
• InChIKey: IBALRBWGSVJPAP-HEHNFIMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(E)-[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanamide
• IUPAC Traditional name: progabide
• Synonyms: 4-[[(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanamide; Gabren; Gabrene; Halogabide; SL 76-002; SL 76002; Progabide

Database IDs

• CAS Number: 62666-20-0
• PubChem SID: 164232840
• PubChem CID: 6314395

CALCULATED PROPERTIES

• Acid pKa: 8.500369
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.1911228
• LogD (pH = 7.4): 3.2739046
• Log P: 3.3088324
• Molar Refractivity: 87.9506 cm^3
• Polarizability: 33.21229 Å^3
• Polar Surface Area: 75.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Bright Yellow Solid
• Melting Point: 135-137°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P755350

Progabide is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity.

REFERENCES

• Johno, I., et al.: J. Pharm. Sci., 71, 633 (1982)
• Shestakova., et al.: Bull. Exp. Biol. Med., 137, 255 (1982)