2-[(1Z)-5-fluoro-2-methyl-1-{[4-(methylsulfanyl)phenyl]methylidene}-1H-inden-3-yl]acetic acid

• ChemBase ID: 132926
• Molecular Formular: C20H17FO2S
• Molecular Mass: 340.4111832
• Monoisotopic Mass: 340.093329
• SMILES: CC1=C(c2cc(ccc2/C/1=C\c1ccc(cc1)SC)F)CC(=O)O
• Canonical SMILES: CSc1ccc(cc1)/C=C/1\c2ccc(cc2C(=C1C)CC(=O)O)F
• InChI: InChI=1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
• InChIKey: LFWHFZJPXXOYNR-MFOYZWKCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1Z)-5-fluoro-2-methyl-1-{[4-(methylsulfanyl)phenyl]methylidene}-1H-inden-3-yl]acetic acid
• IUPAC Traditional name: [(3Z)-6-fluoro-2-methyl-3-{[4-(methylsulfanyl)phenyl]methylidene}inden-1-yl]acetic acid
• Synonyms: (Z)-5-Fluoro-2-methyl-1-[p-(methylthio)benzylidene]indene-3-acetic acid; Sulindac sulfide; Sulindac Sulfide

Database IDs

• CAS Number: 49627-27-2; 32004-67-4
• EC Number: 250-892-2
• MDL Number: MFCD00869764
• PubChem SID: 162227203; 24899543
• PubChem CID: 5352624

CALCULATED PROPERTIES

• Acid pKa: 4.1580195
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4624636
• LogD (pH = 7.4): 1.7593806
• Log P: 4.820957
• Molar Refractivity: 97.9561 cm^3
• Polarizability: 36.855457 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; DMSO; DMSO: ≥22 mg/mL; Methanol
• Apperance: yellow solid; Yellow Solid
• Melting Point: 177-182°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22-42/43
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H334-H361
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - S3131

Biochem/physiol Actions
Sulindac sulfide is a non-steroidal anti-inflammatory compound with a preference for COX-1; it is an inhibitor of Ras activation of Raf-1. It impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP by p120GAP. It is an active metabolite of sulindac. It is also shown to inhibit growth and induce apoptosis in human prostate cancer cells through a COX-1 and COX-2 independent mechanism.

Toronto Research Chemicals - S699220

An active metabolite of Sulindac. Inhibits cyclooxygenase, but induces apoptosis by a cyclooxygenase-independent mechanism. Inhibition of Ras activation of Ref-1. Impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP by p120

REFERENCES

• Hermann, C., et al.: Oncogene, 17, 1769 (1998)
• Lim, T.J., et al.: Biochem. Pharmacol., 58, 1097 (1998)
• Zhang, Z. and DuBois, R.N.: Gastroenterology, 118, 1012 (1998)