524684-52-4
524684-52-4 結(jié)構(gòu)式
基本信息
2-(3-氟-4-羥基苯基)-7-乙烯基-1,3-苯并惡唑-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
物理化學(xué)性質(zhì)
制備方法
74-85-1
544704-73-6
524684-52-4
例1; 2-(3-氟-4-羥基苯基)-7-乙烯基苯并[d]惡唑-5-醇的制備 向2加侖氫化器中加入7-溴-2-(3-氟-4-羥基苯基)苯并[d]惡唑-5-醇（300g，0.926摩爾）、三鄰甲苯基膦（9.1克，3.3%）、二乙酸鈀（2.1克，1%）、乙腈（4.5升）和三乙胺（375克，4當(dāng)量）。用氮?dú)夂鸵蚁_洗氫化器；然后將壓力調(diào)節(jié)至50psi。將反應(yīng)混合物加熱至75℃并保持16小時，此時HPLC分析表明剩余0.2%的原料。將混合物冷卻至35-40℃并通過0.2μm濾柱過濾，并用1,2-二乙氧基乙烷（1.2L）洗滌。將濾液在減壓下濃縮至1.2L，加入水（1.5L）和1,2-二乙氧基乙烷（1.2L）。通過在15-20℃下緩慢加入1.4L的2N NaOH溶液將pH調(diào)節(jié)至11-12。分離各相，并用水（300mL）和2N NaOH（20mL）萃取有機(jī)相。將合并的水相用1,2-二乙氧基乙烷（2×900mL）洗滌。通過在15-20℃下加入500mL 4N HCl將pH調(diào)節(jié)至2.5-3.5。保持4小時后，濾出固體并用水（3×200mL）洗滌。將濕濾餅懸浮于丙酮（1822mL）中并加熱至54-60℃直至完全溶解。在保持54-60℃的同時，于0.5小時內(nèi)滴加乙腈（1822mL）。通過常壓蒸餾將溶液濃縮至1.8-2.0L，然后將濃縮物冷卻至45-50℃并保持0.5小時；隨后冷卻至-3至3℃并保持1小時。濾出固體并用預(yù)冷的乙腈（2×200mL）洗滌；然后在55-65℃和5-10mmHg的真空烘箱中干燥24小時，得到180g（產(chǎn)率71.5%）目標(biāo)產(chǎn)物。將上述產(chǎn)物在75-80℃下溶于乙酸乙酯（23體積）中。將所得溶液冷卻至25-45℃并用活性炭處理。濾液在常壓下濃縮至7體積，向淤漿中加入庚烷（6體積），同時保持溫度在75-80℃。然后將溶液冷卻至45-50℃，保持0.5小時，隨后冷卻至0-5℃，并保持1小時。濾出固體，在55-65℃、5-10mmHg下干燥，得到87%的回收率和99.4%的純度。
參考文獻(xiàn)：
[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
| 報(bào)價(jià)日期 | 產(chǎn)品編號 | 產(chǎn)品名稱 | CAS號 | 包裝 | 價(jià)格 |
| 2026/06/05 | HY-14933 | 普林貝瑞 Prinaberel | 524684-52-4 | 1 mg | 383元 |
| 2026/06/05 | HY-14933 | 普林貝瑞 Prinaberel | 524684-52-4 | 5 mg | 843元 |
| 2026/06/05 | HY-14933 | 普林貝瑞 Prinaberel | 524684-52-4 | 10mM * 1mLin DMSO | 927元 |
常見問題列表
|
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. |