2,5-dichloro-N-(2-methyl-4-nitrophenyl)benzene-1-sulfonamide

• ChemBase ID: 153682
• Molecular Formular: C13H10Cl2N2O4S
• Molecular Mass: 361.2005
• Monoisotopic Mass: 359.97383317
• SMILES: Cc1cc(ccc1NS(=O)(=O)c1cc(ccc1Cl)Cl)[N+](=O)[O-]
• Canonical SMILES: Clc1ccc(c(c1)S(=O)(=O)Nc1ccc(cc1C)[N+](=O)[O-])Cl
• InChI: InChI=1S/C13H10Cl2N2O4S/c1-8-6-10(17(18)19)3-5-12(8)16-22(20,21)13-7-9(14)2-4-11(13)15/h2-7,16H,1H3
• InChIKey: AXNUEXXEQGQWPA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dichloro-N-(2-methyl-4-nitrophenyl)benzene-1-sulfonamide
• IUPAC Traditional name: 2,5-dichloro-N-(2-methyl-4-nitrophenyl)benzenesulfonamide
• Synonyms: 2,5-Dichloro-N-(2-methyl-4-nitrophenyl)benzenesulfonamide; N-(2-Methyl-4-nitrophenyl)-2,5-dichlorobenzenesulfonamide; FH535

Database IDs

• CAS Number: 108409-83-2
• MDL Number: MFCD01212888
• PubChem SID: 162247821
• PubChem CID: 3463933

CALCULATED PROPERTIES

• Acid pKa: 6.8377295
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.1051655
• LogD (pH = 7.4): 3.6061022
• Log P: 4.122406
• Molar Refractivity: 84.8657 cm^3
• Polarizability: 32.75827 Å^3
• Polar Surface Area: 91.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 36
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H10Cl2N2O4S

DETAILS

Sigma Aldrich - F5682

Biochem/physiol Actions
FH535 is a reversible dual inhibitor of Wnt/β-catenin and a PPARγ and PPARδ signaling antagonist. FH535 is unique in its ability to inhibit the Wnt/β-catenin pathway. The compound is selectively toxic to some carcinomas expressing the Wnt/β-catenin pathway.

Toronto Research Chemicals - M325350

Antagonizes Wnt/β-catenin/Tcf-mediated transcription as well as PPARγ and δ activity. Able to inhibit the recruitment of the co-activators β-catenin and GRIP1, both of which are activators for both pathways.

REFERENCES

• Handeli, S., et al.: Mol. Cancer Ther., 7, 521 (2008)