N-(4-bromophenyl)-3-[(4-bromophenyl)sulfamoyl]benzamide

• ChemBase ID: 153869
• Molecular Formular: C19H14Br2N2O3S
• Molecular Mass: 510.19906
• Monoisotopic Mass: 507.90918732
• SMILES: c1cc(cc(c1)S(=O)(=O)Nc1ccc(cc1)Br)C(=O)Nc1ccc(cc1)Br
• Canonical SMILES: Brc1ccc(cc1)NC(=O)c1cccc(c1)S(=O)(=O)Nc1ccc(cc1)Br
• InChI: InChI=1S/C19H14Br2N2O3S/c20-14-4-8-16(9-5-14)22-19(24)13-2-1-3-18(12-13)27(25,26)23-17-10-6-15(21)7-11-17/h1-12,23H,(H,22,24)
• InChIKey: SJJKUNDBFWUAQB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-bromophenyl)-3-[(4-bromophenyl)sulfamoyl]benzamide
• IUPAC Traditional name: N-(4-bromophenyl)-3-[(4-bromophenyl)sulfamoyl]benzamide
• Synonyms: C2-8; N-(4-Bromophenyl)-3-[[(4-bromophenyl)amino]sulfonyl]benzamide

Database IDs

• CAS Number: 300670-16-0
• MDL Number: MFCD00355835
• PubChem SID: 162248008; 24724418
• PubChem CID: 1076689

CALCULATED PROPERTIES

• Acid pKa: 7.698871
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.087876
• LogD (pH = 7.4): 4.9376774
• Log P: 5.090301
• Molar Refractivity: 113.6693 cm^3
• Polarizability: 43.471115 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ~20 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H14Br2N2O3S

DETAILS

Sigma Aldrich - B3436

Biochem/physiol Actions
N-(4-Bromophenyl)-3-[[(4-bromophenyl)amino]sulfonyl]benzamide is the first inhibitor of aggregation of the polyglutamine (polyQ) sequence of the Huntington′s Disease protein (huntingtin); polyQ aggregation is neurotoxic, and inhibitors of aggregation may be therapeutic in HD and other polyQ diseases; C2-8 inhibited aggregation in HD PC12 cells with an IC50 of 50nM; when administered in food, suppressed neurodegeneration in vivo in the Drosophila HD model.