Prinaberel
- Product Name
- Prinaberel
- CAS No.
- 524684-52-4
- Chemical Name
- Prinaberel
- Synonyms
- ERB 041;PRINABEREL;WAY-202041;Prinaberel (ERB 041);2-(3-Fluoro-4-hydroxyphenyl)- 7-vinylbenzoxazol-5-ol;7-Ethenyl-2-(3-fluoro-4-hydroxyphenyl)-5-benzoxazolol;2-(3-Fluoro-4-hydroxyphenyl)-7-vinylbenzo[d]oxazol-5-ol;5-Benzoxazolol, 7-ethenyl-2-(3-fluoro-4-hydroxyphenyl)-;2-(3-Fluoro-4-hydroxyphenyl)-7-vinyl-1,3-benzoxazol-5-ol
- CBNumber
- CB21509128
- Molecular Formula
- C15H10FNO3
- Formula Weight
- 271.24
- MOL File
- 524684-52-4.mol
Prinaberel Property
- Melting point:
- 250-252 ºC
- Boiling point:
- 451.6±45.0 °C(Predicted)
- Density
- 1.413
- storage temp.
- room temp
- solubility
- DMSO: ≥25mg/mL
- form
- powder
- pka
- 7.50±0.20(Predicted)
- color
- white to tan
- InChIKey
- MQIMZDXIAHJKQP-UHFFFAOYSA-N
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- PZ0183
- Product name
- ERB-041
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $128
- Updated
- 2025/07/31
- Product number
- PZ0183
- Product name
- ERB-041
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $547
- Updated
- 2024/03/01
- Product number
- 28737
- Product name
- ERB 041
- Packaging
- 1mg
- Price
- $36
- Updated
- 2024/03/01
- Product number
- 28737
- Product name
- ERB 041
- Packaging
- 5mg
- Price
- $87
- Updated
- 2024/03/01
- Product number
- 28737
- Product name
- ERB 041
- Packaging
- 10mg
- Price
- $155
- Updated
- 2024/03/01
Prinaberel Chemical Properties,Usage,Production
Chemical Properties
Pale Yellow Solid
Uses
ERB 041 is a potent ERβ agonist; displays >200-fold selectivity for ERβ over ERα (IC50 values are 5 and 1216 nM for human ERβ and ERα; 3.1 and 620 nM for rat ERβ and ERα; and 3.7 and 750 nM for mouse ERβ and ERα respectively).
Uses
Prinaberel is a potent ERβ agonist; displays >200-fold selectivity for ERβ over ERα (IC50 values are 5 and 1216 nM for human ERβ and ERα; 3.1 and 620 nM for rat ERβ and ERα; and 3.7 and 750 nM for mouse ERβ and ERα respectively).
Biological Activity
ERB-041 is a potent, selective estrogen ERβ receptor agonist (IC50 ERβ: 5.4 nM; > 200-fold selective over ERα). ERβ plays a minor role in mediating estrogen action in the uterus, the hypothalamus/pituitary, the skeleton, and other classic estrogen target tissues. However, a clear role for ERβ has been established in the ovary, cardiovascular system, and brain as well as in animal models of inflammation including arthritis, endometriosis, inflammatory bowel disease, and sepsis. There is increasing interest in finding ERβ agonists for potential use in a variety of clinical applications without triggering classic estrogenic side effects.
Synthesis
74-85-1
544704-73-6
524684-52-4
Example 1; Preparation of 2-(3-fluoro-4-hydroxyphenyl)-7-vinylbenzo[d]oxazol-5-ol To a 2-gallon hydrogenator was added 7-bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol (300 g, 0.926 mol), tri-o-tolylphosphine (9.1 g, 3.3%), palladium diacetate (2.1 g, 1%), acetonitrile (4.5 liters), and triethylamine (375 g, 4 equiv). The hydrogenator was flushed with nitrogen and ethylene; the pressure was then adjusted to 50 psi. the reaction mixture was heated to 75 °C and held for 16 h, at which point HPLC analysis showed 0.2% of the feedstock remaining. The mixture was cooled to 35-40 °C and filtered through a 0.2 μm filter column and washed with 1,2-diethoxyethane (1.2 L). The filtrate was concentrated to 1.2 L under reduced pressure and water (1.5 L) and 1,2-diethoxyethane (1.2 L) were added. The pH was adjusted to 11-12 by slowly adding 1.4 L of 2N NaOH solution at 15-20 °C. The phases were separated and the organic phase was extracted with water (300 mL) and 2N NaOH (20 mL). The combined aqueous phases were washed with 1,2-diethoxyethane (2 x 900 mL). The pH was adjusted to 2.5-3.5 by adding 500 mL of 4N HCl at 15-20 °C. After holding for 4 h, the solid was filtered out and washed with water (3 × 200 mL). The wet filter cake was suspended in acetone (1822mL) and heated to 54-60°C until completely dissolved. Acetonitrile (1822mL) was added dropwise over 0.5 hours while maintaining 54-60°C. The solution was concentrated to 1.8-2.0 L by distillation at atmospheric pressure, then the concentrate was cooled to 45-50 °C and held for 0.5 h; it was then cooled to -3 to 3 °C and held for 1 h. The solution was concentrated to 1.8-2.0 L by distillation at atmospheric pressure. The solid was filtered out and washed with pre-cooled acetonitrile (2 x 200 mL); it was then dried in a vacuum oven at 55-65 °C and 5-10 mmHg for 24 h to give 180 g (71.5% yield) of the target product. The above product was dissolved in ethyl acetate (23 v/v) at 75-80 °C. The resulting solution was cooled to 25-45 °C and treated with activated carbon. The filtrate was concentrated to 7 volumes at atmospheric pressure and heptane (6 volumes) was added to the slurry while maintaining the temperature at 75-80 °C. The solution was then cooled to 45-50 °C and held for 0.5 h. It was subsequently cooled to 0-5 °C and held for 1 h. The slurry was then treated with activated carbon. The solid was filtered out and dried at 55-65°C and 5-10 mmHg to give 87% recovery and 99.4% purity.
in vivo
Prinaberel (2mg/mouse; topically; 30 min prior to UVB irradiation for 30 weeks) suppresses development of squamous cell carcinoma in SKH-1 hairless mice[2].
Prinaberel reduces proliferation and angiogenesis and induces apoptosis in UVB-induced skin tumors. Prinaberel suppresses pro-inflammatory signaling pathway in UVB-induced skin tumors. Prinaberel diminished tumor invasiveness via PI3K-AKT pathway and WNT signaling[2].
| Animal Model: | Six- to eight-weeks-old SKH-1 hairless female mice[2] |
| Dosage: | 2 mg/mouse in 200μl ethanol |
| Administration: | Topically; 30 min prior to UVB (180mJ/cm2) irradiation for 30 weeks |
| Result: | Diminished UVB-induced skin tumor development in SKH-1 hairless mice. |
IC 50
hERβ: 5.4 nM (IC50); rat ERβ: 3.1 nM (IC50); mouse ERβ: 3.7 nM (IC50); hERα: 1200 nM (IC50); mouse ERα: 750 nM (IC50); rat ERα: 620 nM (IC50)
storage
Store at -20°C
References
[1] Patent: US2006/199967, 2006, A1. Location in patent: Page/Page column 5-6
[2] Patent: US2006/199852, 2006, A1. Location in patent: Page/Page column 6
Prinaberel Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Prinaberel manufacturers
- Product
- Prinaberel 524684-52-4
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 100kg
- Release date
- 2020-01-18