(3Z)-3-(1H-indol-3-ylmethylidene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonamide

• ChemBase ID: 167633
• Molecular Formular: C17H13N3O3S
• Molecular Mass: 339.36842
• Monoisotopic Mass: 339.06776229
• SMILES: c1(c[nH]c2c1cccc2)/C=C\1/c2c(NC1=O)ccc(c2)S(=O)(=O)N
• Canonical SMILES: O=C1Nc2c(/C/1=C/c1c[nH]c3c1cccc3)cc(cc2)S(=O)(=O)N
• InChI: InChI=1S/C17H13N3O3S/c18-24(22,23)11-5-6-16-13(8-11)14(17(21)20-16)7-10-9-19-15-4-2-1-3-12(10)15/h1-9,19H,(H,20,21)(H2,18,22,23)/b14-7-
• InChIKey: AFTGOSQNWXOYGE-AUWJEWJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3Z)-3-(1H-indol-3-ylmethylidene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonamide
• IUPAC Traditional name: (3Z)-3-(1H-indol-3-ylmethylidene)-2-oxo-1H-indole-5-sulfonamide
• Synonyms: 2,3-Dihydro-3-(1H-indol-3-ylmethylene)-2-oxo-1H-indole-5-sulfonamide

Database IDs

• CAS Number: 181223-16-5
• PubChem SID: 162261766
• PubChem CID: 22978714

CALCULATED PROPERTIES

• Acid pKa: 10.0483
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.9700118
• LogD (pH = 7.4): 1.9691464
• Log P: 1.9700229
• Molar Refractivity: 92.9757 cm^3
• Polarizability: 36.27989 Å^3
• Polar Surface Area: 105.05 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol (Sparingly); Methanol (Sparingly)
• Apperance: Brownish Yellow Solid
• Melting Point: >300°C

DETAILS

Toronto Research Chemicals - D449148

A potent small molecule inhibitor of spleen tyrosine kinase (Syk).

REFERENCES

• Pivniouk, V., et al.: J. Clin. Invest., 103, 1737 (1999)
• Clark, D., et al.: Drug Discov. Today, 5, 49 (1999)
• Sedlik, C., et al.: J. Immunol., 170, 846 (1999)