2-[(4-phenoxybenzenesulfonyl)methyl]thiirane

• ChemBase ID: 154519
• Molecular Formular: C15H14O3S2
• Molecular Mass: 306.39986
• Monoisotopic Mass: 306.03843631
• SMILES: c1ccc(cc1)Oc1ccc(cc1)S(=O)(=O)CC1CS1
• Canonical SMILES: O=S(=O)(c1ccc(cc1)Oc1ccccc1)CC1SC1
• InChI: InChI=1S/C15H14O3S2/c16-20(17,11-14-10-19-14)15-8-6-13(7-9-15)18-12-4-2-1-3-5-12/h1-9,14H,10-11H2
• InChIKey: LSONWRHLFZYHIN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-phenoxybenzenesulfonyl)methyl]thiirane
• IUPAC Traditional name: 2-[(4-phenoxybenzenesulfonyl)methyl]thiirane
• Synonyms: 2-[[(4-phenoxyphenyl)sulfonyl]methyl]-Thiirane; SB-3CT

Database IDs

• CAS Number: 292605-14-2
• MDL Number: MFCD09836266
• PubChem SID: 162248658
• PubChem CID: 9883002

CALCULATED PROPERTIES

• Acid pKa: 18.956602
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.7467816
• LogD (pH = 7.4): 2.7467816
• Log P: 2.7467816
• Molar Refractivity: 80.8635 cm^3
• Polarizability: 32.648422 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• 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
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H14O3S2

DETAILS

Sigma Aldrich - S1326

Legal Information
Sold under license of U.S. Patent 6,703,415.
Biochem/physiol Actions
SB-3CT is a potent matrix metalloproteinase MMP-2 and MMP-9 inhibitor. Matrix metalloproteinases (MMPs) are involved in a number of activities including angiogenesis and embryogenesis. In particular, gelatinases A (MMP-2) and B (MMP-9), are thought to facilitate tumor metastasis. SB-3CT exhibits a covalent mechanism based behavior in inhibition of MMP-2 and MMP-9. This inhibitor appears to have similarity to TIMP-1 and TIMP-2 in the slow-binding component of inhibition. SB-3CT has been shown to directly bind to the zinc in the catalytic site of MMP-2. SB-3CT does not affect the activities of MMP-1 (Ki = 206 μM) MMP-3 (Ki = 15 μM), or MMP-7 (Ki = 96 μM).