1,3-bis[2-hydroxy-5-(trifluoromethyl)phenyl]urea

• ChemBase ID: 153988
• Molecular Formular: C15H10F6N2O3
• Molecular Mass: 380.2419192
• Monoisotopic Mass: 380.05956151
• SMILES: c1cc(c(cc1C(F)(F)F)NC(=O)Nc1cc(ccc1O)C(F)(F)F)O
• Canonical SMILES: O=C(Nc1cc(ccc1O)C(F)(F)F)Nc1cc(ccc1O)C(F)(F)F
• InChI: InChI=1S/C15H10F6N2O3/c16-14(17,18)7-1-3-11(24)9(5-7)22-13(26)23-10-6-8(15(19,20)21)2-4-12(10)25/h1-6,24-25H,(H2,22,23,26)
• InChIKey: NJFVQMRYJZHGME-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis[2-hydroxy-5-(trifluoromethyl)phenyl]urea
• IUPAC Traditional name: 1,3-bis[2-hydroxy-5-(trifluoromethyl)phenyl]urea
• Synonyms: NS1643

Database IDs

• CAS Number: 448895-37-2
• MDL Number: MFCD08705418
• PubChem SID: 24897438; 162248127
• PubChem CID: 10177784

CALCULATED PROPERTIES

• Acid pKa: 8.260607
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): 4.2664733
• LogD (pH = 7.4): 4.2097526
• Log P: 4.2672215
• Molar Refractivity: 81.962 cm^3
• Polarizability: 28.059292 Å^3
• Polar Surface Area: 81.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H10F6N2O3

DETAILS

Sigma Aldrich - N0663

Biochem/physiol Actions
The new diphenylurea compound 1,3-bis-(2-hydroxy-5-trifluoromethyl-phenyl)-urea (NS1643) was tested in hERG channel. In Xenopus laevis oocytes, NS1643 increased both steady-state and tail current at all voltages tested. The EC50 value for hERG channel activation was 10.5 μM. The effect could be reverted by application of the specific hERG channel inhibitor 4′-[[1-[2-(6-methyl-2-pyridyl)ethyl]-4-piperidinyl]carbonyl]-methanesulfonanilide (E-4031) at 100 nM. Application of NS1643 also resulted in a prolonged postrepolarization refractory time. hERG channel activation by small molecules such as NS1643 increases the repolarization reserve and presents a new antiarrhythmic approach.