| Identification | Back Directory | [Name]
7-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol | [CAS]
440122-66-7 | [Synonyms]
WAY 200070
WAY200070;WAY 200070
7-bromo-2-(4-hydroxyphenyl)-5-benzoxazolol
5-Benzoxazolol, 7-bromo-2-(4-hydroxyphenyl)-
7-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol | [EINECS(EC#)]
604-604-1 | [Molecular Formula]
C13H8BrNO3 | [MDL Number]
MFCD16618385 | [MOL File]
440122-66-7.mol | [Molecular Weight]
306.11 |
| Chemical Properties | Back Directory | [Boiling point ]
463.6±35.0 °C(Predicted) | [density ]
1.720±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT | [solubility ]
DMSO: ≥20mg/mL | [form ]
solid | [pka]
7.26±0.40(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
WAY 200070 is an aryl diphenolic azole and a selective ERβ agonist. This compound is suitable for estrogen receptor signaling research. | [Biological Activity]
WAY-200070 is a selective estrogen receptor agonist with IC50 of 2.3 nM. | [Synthesis]
Step e) Route for the synthesis of 7-bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol a) The operation was as follows: boron tribromide (1M, 89.9 mL, 89.8 mmol) was added dropwise to a mixture of 7-bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazolol (10.0 g, 29.94 mmol) in suspension at -70 °C with dichloromethane (50 mL) in suspension. The reaction mixture was gradually warmed up to room temperature, during which the suspension transformed into a black solution. After continuous stirring of the reaction mixture for 2 days at room temperature, it was slowly poured into pre-cooled (0 °C) ether (1000 mL). Subsequently, methanol (200 mL) was slowly added to the above mixture over a period of 20 minutes. The mixture was poured into water (1.5 L) and the organic layer was separated, washed three times with water and dried with anhydrous magnesium sulfate. After concentration by evaporation, the product was crystallized from a mixed solvent of acetone/ether/hexane to give an off-white solid product (8.4 g, 92% yield, melting point 298-299 °C); mass spectrometry analysis showed m/e 306 (M + H)+. | [in vivo]
Administration of WAY-200070 (30 mg/kg sc) causes nuclear translocation of ERRβ receptors in WT mice. Administration of it produces a delayed 50% increase in dopamine in the striatum of wild type mice. It reduces immobility time in the mouse tail suspension test indicating an antidepressant-like effect. In gonadally intact male and female mice WAY-200070 increases agonistic behaviors such as pushing down and aggressive grooming, while leaving attacks unaffected. Ovariectomized (ovx) mice treated with PPT fail to learn the socially acquired preference, while WAY-200070-treated ovx mice shows a two-fold prolonged preference for the food eaten by their demonstrator. WAY-200070 , shows significantly decreased anxiety-like behaviors in both the open-field and elevated plus maze and significantly less depressive-like behaviors in the forced swim test. < /div> | [target]
IC50: 2.3 nM (ERRβ), 155 nM (ERRα) | [IC 50]
ERβ: 2.3 nM (IC50); ERα: 155 nM (IC50) | [storage]
Store at RT | [References]
[1] Patent: US2003/199562, 2003, A1 |
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