5-({5-bromo-2-[(2-bromophenyl)methoxy]phenyl}methylidene)-2-sulfanylidene-1,3-thiazolidin-4-one

• ChemBase ID: 153897
• Molecular Formular: C17H11Br2NO2S2
• Molecular Mass: 485.21274
• Monoisotopic Mass: 482.8597946
• SMILES: c1ccc(c(c1)COc1ccc(cc1/C=C\1/C(=O)NC(=S)S1)Br)Br
• Canonical SMILES: S=C1NC(=O)/C(=C/c2cc(Br)ccc2OCc2ccccc2Br)/S1
• InChI: InChI=1S/C17H11Br2NO2S2/c18-12-5-6-14(22-9-10-3-1-2-4-13(10)19)11(7-12)8-15-16(21)20-17(23)24-15/h1-8H,9H2,(H,20,21,23)
• InChIKey: HXNBAOLVPAWYLT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({5-bromo-2-[(2-bromophenyl)methoxy]phenyl}methylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• IUPAC Traditional name: 5-({5-bromo-2-[(2-bromophenyl)methoxy]phenyl}methylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• Synonyms: 5-[[5-bromo-2-[(2-bromophenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone; Phosphatase of regenerating liver-3, Inhibitor I; PRL-3 Inhibitor I

Database IDs

• CAS Number: 893449-38-2
• MDL Number: MFCD11045303
• PubChem SID: 162248036
• PubChem CID: 11983303

CALCULATED PROPERTIES

• Acid pKa: 7.4822025
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.839686
• LogD (pH = 7.4): 5.5863442
• Log P: 5.8441358
• Molar Refractivity: 110.5333 cm^3
• Polarizability: 42.21288 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: <2 mg/mL
• Apperance: yellow solid

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/37/38-50/53
• Safety Statements: 26-36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H410
• GHS Precautionary statements: P261-P273-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H11Br2NO2S2

DETAILS

Sigma Aldrich - P0108

Biochem/physiol Actions
PRL-3 Inhibitor I is a rhodanine derivative with an IC50 value of 0.9 μM against phosphatase of regenerating liver-3 (PRL-3), a nonclassical protein tyrosine phosphatase that has recently been shown to be involved in cancer metastasis. PRL-3 Inhibitor I reduced the invasiveness of B16F10 melanoma cells in a cell based assay.