5-amino-1-(4-methoxybenzenesulfonyl)-1H-pyrazol-3-yl benzoate

• ChemBase ID: 154643
• Molecular Formular: C17H15N3O5S
• Molecular Mass: 373.3831
• Monoisotopic Mass: 373.0732416
• SMILES: COc1ccc(cc1)S(=O)(=O)n1c(cc(n1)OC(=O)c1ccccc1)N
• Canonical SMILES: COc1ccc(cc1)S(=O)(=O)n1nc(cc1N)OC(=O)c1ccccc1
• InChI: InChI=1S/C17H15N3O5S/c1-24-13-7-9-14(10-8-13)26(22,23)20-15(18)11-16(19-20)25-17(21)12-5-3-2-4-6-12/h2-11H,18H2,1H3
• InChIKey: FQICFDBMQBCJDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-(4-methoxybenzenesulfonyl)-1H-pyrazol-3-yl benzoate
• IUPAC Traditional name: 5-amino-1-(4-methoxybenzenesulfonyl)pyrazol-3-yl benzoate
• Synonyms: SID 852843; Benzoic acid 5-amino-1-(4-methoxy-benzenesulfonyl)-1H-pyrazol-3-yl ester

Database IDs

• CAS Number: 909859-19-4
• MDL Number: MFCD04453813
• PubChem SID: 162248781
• PubChem CID: 655490

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.565389
• LogD (pH = 7.4): 2.5653906
• Log P: 2.5653906
• Molar Refractivity: 95.299 cm^3
• Polarizability: 36.732666 Å^3
• Polar Surface Area: 113.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H15N3O5S

DETAILS

Sigma Aldrich - S3451

Biochem/physiol Actions
SID 852843 is an inhibitor of West Nile Virus NS2B-NS3 proteinase. Flaviviruses, such as West Nile and Dengue, are a threat to humans from both public health and bioterrorism perspectives. The NS3 proteinase is essential for flaviviral maturation. Inhibitors of NS3 are sought for treatment and prophylactic therapeutics. The NIH molecular library was screened for activity against West Nile Virus NS3, resulting in the discovery of SID 852843. This compound inhibits the NS3 proteinase of West Nile, but not of Dengue type 2 virus. SID 852843 is a reversible, allosteric inhibitor of the formation of the functional conformation of the NS3 proteinase. This is the first flaviviral proteinase inhibitor with the potential to lead to a drug. Aprotinin is an efficient inhibitor of NS3, but it is not selective and has low penetration into cells, limiting its potential for therapeutic use.