5-(5,6-dimethoxy-1H-1,3-benzodiazol-1-yl)-3-{[2-(trifluoromethyl)phenyl]methoxy}thiophene-2-carboxamide

• ChemBase ID: 153938
• Molecular Formular: C22H18F3N3O4S
• Molecular Mass: 477.4562296
• Monoisotopic Mass: 477.09701173
• SMILES: COc1cc2c(cc1OC)n(cn2)c1cc(c(s1)C(=O)N)OCc1ccccc1C(F)(F)F
• Canonical SMILES: COc1cc2c(cc1OC)ncn2c1cc(c(s1)C(=O)N)OCc1ccccc1C(F)(F)F
• InChI: InChI=1S/C22H18F3N3O4S/c1-30-16-7-14-15(8-17(16)31-2)28(11-27-14)19-9-18(20(33-19)21(26)29)32-10-12-5-3-4-6-13(12)22(23,24)25/h3-9,11H,10H2,1-2H3,(H2,26,29)
• InChIKey: JSKUWFIZUALZLX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(5,6-dimethoxy-1H-1,3-benzodiazol-1-yl)-3-{[2-(trifluoromethyl)phenyl]methoxy}thiophene-2-carboxamide
• IUPAC Traditional name: 5-(5,6-dimethoxy-1,3-benzodiazol-1-yl)-3-{[2-(trifluoromethyl)phenyl]methoxy}thiophene-2-carboxamide
• Synonyms: 5-(5,6-dimethoxy-1H-benzimidazol-1-yl)-3-{[2-(trifluoromethyl)-benzyl]oxy}thiophene-2-carboxamide; GW843682; GW843682X

Database IDs

• CAS Number: 660868-91-7
• MDL Number: MFCD09971143
• PubChem SID: 162248077
• PubChem CID: 9826308

CALCULATED PROPERTIES

• Acid pKa: 14.144923
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.5188189
• LogD (pH = 7.4): 3.0382736
• Log P: 3.0541
• Molar Refractivity: 125.0662 cm^3
• Polarizability: 44.01048 Å^3
• Polar Surface Area: 88.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H413
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H18F3N3O4S

DETAILS

Sigma Aldrich - G2171

Biochem/physiol Actions
GW843682X is a polo-like kinase-1 (PLK1) and polo-like kinase-3 (PLK3) inhibitor with nanomolar activity. It shows potent inhibition of proliferation of a wide variety of tumor cell lines.