524684-52-4
524684-52-4 结构式
基本信息
2-(3-氟-4-羟基苯基)-7-乙烯基-1,3-苯并恶唑-5-醇
PRINABEREL
WAY-202041
Prinaberel (ERB 041)
2-(3-Fluoro-4-hydroxyphenyl)- 7-vinylbenzoxazol-5-ol
7-Ethenyl-2-(3-fluoro-4-hydroxyphenyl)-5-benzoxazolol
5-Benzoxazolol, 7-ethenyl-2-(3-fluoro-4-hydroxyphenyl)-
2-(3-Fluoro-4-hydroxyphenyl)-7-vinyl-1,3-benzoxazol-5-ol
物理化学性质
制备方法
74-85-1
544704-73-6
524684-52-4
例1; 2-(3-氟-4-羟基苯基)-7-乙烯基苯并[d]恶唑-5-醇的制备 向2加仑氢化器中加入7-溴-2-(3-氟-4-羟基苯基)苯并[d]恶唑-5-醇（300g，0.926摩尔）、三邻甲苯基膦（9.1克，3.3%）、二乙酸钯（2.1克，1%）、乙腈（4.5升）和三乙胺（375克，4当量）。用氮气和乙烯冲洗氢化器；然后将压力调节至50psi。将反应混合物加热至75℃并保持16小时，此时HPLC分析表明剩余0.2%的原料。将混合物冷却至35-40℃并通过0.2μm滤柱过滤，并用1,2-二乙氧基乙烷（1.2L）洗涤。将滤液在减压下浓缩至1.2L，加入水（1.5L）和1,2-二乙氧基乙烷（1.2L）。通过在15-20℃下缓慢加入1.4L的2N NaOH溶液将pH调节至11-12。分离各相，并用水（300mL）和2N NaOH（20mL）萃取有机相。将合并的水相用1,2-二乙氧基乙烷（2×900mL）洗涤。通过在15-20℃下加入500mL 4N HCl将pH调节至2.5-3.5。保持4小时后，滤出固体并用水（3×200mL）洗涤。将湿滤饼悬浮于丙酮（1822mL）中并加热至54-60℃直至完全溶解。在保持54-60℃的同时，于0.5小时内滴加乙腈（1822mL）。通过常压蒸馏将溶液浓缩至1.8-2.0L，然后将浓缩物冷却至45-50℃并保持0.5小时；随后冷却至-3至3℃并保持1小时。滤出固体并用预冷的乙腈（2×200mL）洗涤；然后在55-65℃和5-10mmHg的真空烘箱中干燥24小时，得到180g（产率71.5%）目标产物。将上述产物在75-80℃下溶于乙酸乙酯（23体积）中。将所得溶液冷却至25-45℃并用活性炭处理。滤液在常压下浓缩至7体积，向淤浆中加入庚烷（6体积），同时保持温度在75-80℃。然后将溶液冷却至45-50℃，保持0.5小时，随后冷却至0-5℃，并保持1小时。滤出固体，在55-65℃、5-10mmHg下干燥，得到87%的回收率和99.4%的纯度。
参考文献：
[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
| 报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
| 2025/05/22 | HY-14933 | 普林贝瑞 Prinaberel | 524684-52-4 | 1 mg | 383元 |
| 2025/05/22 | HY-14933 | 普林贝瑞 Prinaberel | 524684-52-4 | 5 mg | 843元 |
| 2025/05/22 | HY-14933 | 普林贝瑞 Prinaberel | 524684-52-4 | 10mg | 1350元 |
常见问题列表
|
hERβ 5.4 nM (IC 50 ) |
rat ERβ 3.1 nM (IC 50 ) |
mouse ERβ 3.7 nM (IC 50 ) |
hERα 1200 nM (IC 50 ) |
mouse ERα 750 nM (IC 50 ) |
rat ERα 620 nM (IC 50 ) |
Prinaberel (ERB-041) (0-60 µM; 24 hours) treatment of human SCC cells induces cell differentiation, cell cycle arrest and reduces colony formation.
Prinaberel shows a marked reduction in the expression of inflammation regulatory proteins such as p-NFκBp65, iNOS and COX-2 in A431 cells. Prinaberel diminishes phosphorylated-PI3K and -AKT, which is associated with the enhancement in E-cadherin expression and reduction in migration of A431 cells.
Prinaberel (0.01-10 µM) inhibits cell proliferation in a dose- and time-dependent manner.
Prinaberel (10 µM; 48 hours) promotes ovarian cancer (SKOV-3 cells) apoptosis.
Western Blot Analysis
| Cell Line: | A431 cells |
| Concentration: | 0, 20, 40 and 60 µM |
| Incubation Time: | 24 hours |
| Result: | Reduction in the expression of G1 cyclins (D1, D2 and D3) and CDK4. |
Cell Proliferation Assay
| Cell Line: | SKOV-3, A2780CP or OVCAR-3 cells |
| Concentration: | 0.01, 0.1 and 10 µM |
| Incubation Time: | 24-48 hours |
| Result: | Showed significantly inhibitory effect on cell proliferation. |
Prinaberel (2mg/mouse; topically; 30 min prior to UVB irradiation for 30 weeks) suppresses development of squamous cell carcinoma in SKH-1 hairless mice.
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.
| Animal Model: | Six- to eight-weeks-old SKH-1 hairless female mice |
| 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. |