4,5,6,7-四溴-1H-苯并三唑
4,5,6,7-四溴-1H-苯并三唑
4,5,6,7-四溴-1H-苯并三唑 性质
| 熔点 | 262-266°C |
|---|---|
| 沸点 | 552.5±45.0 °C(Predicted) |
| 密度 | 2.840±0.06 g/cm3(Predicted) |
| 储存条件 | 2-8°C |
| 溶解度 | 在DMSO中的溶解度为28 毫克/毫升 |
| 酸度系数(pKa) | 3.87±0.40(Predicted) |
| 形态 | 固体 |
| 颜色 | 白色 |
| 最大波长(λmax) | 300nm(MeOH)(lit.) |
| InChI | 1S/C6HBr4N3/c7-1-2(8)4(10)6-5(3(1)9)11-13-12-6/h(H,11,12,13) |
| InChIKey | OMZYUVOATZSGJY-UHFFFAOYSA-N |
| SMILES | Brc1c(Br)c(Br)c2[nH]nnc2c1Br |
4,5,6,7-四溴-1H-苯并三唑 用途与合成方法
|
CK2 0.15 μM (IC 50 , Human CK2) |
PIM1 1.04 μM (IC 50 ) |
PIM2 4.3 μM (IC 50 ) |
PIM3 0.86 μM (IC 50 ) |
HIPK2 5.3 μM (IC 50 ) |
HIPK3 4.9 μM (IC 50 ) |
DYRK1a 4.36 μM (IC 50 ) |
DYRK2 0.99 μM (IC 50 ) |
DYRK3 5.3 μM (IC 50 ) |
PKD1 5.9 μM (IC 50 ) |
CDK2 14 μM (IC 50 ) |
Investigation of the inhibitory power of TBB with a panel of 33 protein kinases shows highest potency for CK2 (casein kinase 2) (human CK2: IC 50 =1.6 μM at 100 μM ATP). TBB also inhibits three other kinases with less potency: CDK2 (IC 50 =15.6 μM), phosphorylase kinase (IC 50 =8.7 μM) and glycogen synthase kinase 3β (GSK3β) (IC 50 =11.2 μM). All other kinases tested have IC50 values 50-fold greater than that for CK2. The viability of the androgen insensitive PC-3 cells may be diminished by TBB (60 μM TBB) acting either alone or combined with anticancer agents CPT or TRAIL when a proper time schedule of the administration is applied. The time schedule-dependent activity of TBB does not come from its effect on apoptosis in PC-3 cells. TBB is an ATP/GTP competitive inhibitor of protein kinase casein kinase-2 (CK2), has been examined against a panel of 33 protein kinases, either Ser/Thr- or Tyr-specific. In the presence of 10 μM TBB (and 100 μM ATP) only CK2 is drastically inhibited (>85%) whereas three kinases (phosphorylase kinase, glycogen synthase kinase 3L and cyclin-dependent kinase 2/cyclin A) underwent moderate inhibition, with IC 50 values one-two orders of magnitude higher than CK2 (IC 50 =0.9 μM). TBB also inhibits endogenous CK2 in cultured Jurkat cells.
The extent of retinal neovascularization in a mouse OIR model is reduced by approximately 60% after treatment with TBB (6 days at 60 mg/kg per day).
95-14-7
17374-26-4
采用文献[39]报道的方法进行适当修改。将1H-苯并三唑（32，3g）溶解于69% HNO3（50mL）与100% HNO3（3mL）的混合溶液中。随后，将溶液加热至80℃，并在1小时内缓慢滴加Br2（6当量）。反应混合物在60℃下剧烈搅拌48小时后，冷却至室温。在氮气保护下，通过20% Na2S2O5水溶液（100mL）捕集并除去未反应的Br2。接着，将反应混合物倒入冰冷的H2O（200mL）与饱和Na2S2O5水溶液（10mL）的混合液中。过滤收集生成的橙色沉淀，并依次用H2O（50mL）和EtOH（50mL）洗涤。粗产物通过热MeOH（50mL）多次洗涤纯化，得到白色固体4,5,6,7-四溴-1H-苯并三唑（TBBt，34，7.45g，17.14mmol，产率68%）。通过高分辨率质谱（HRMS）确认产物结构。1H NMR、13C NMR及熔点数据与文献报道一致。TBBt 34的性质如下：白色固体；熔点264-266℃（MeOH）[文献值：262-266℃（乙酸）][89]；HRMS（ESI-TOF）m/z：[M + H]+ C9H7Br5N3+ m/z计算值：435.6941，实测值：435.6629。
参考文献：
[1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 307 - 333
[2] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 364 - 374
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 4395,4399
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1573 - 1578
4,5,6,7-四溴-1H-苯并三唑 价格(试剂级)
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2025-12-22 | HY-14394 | 4,5,6,7-四溴-1H-苯并三唑 | 17374-26-4 | 5 mg | 300 |
| 2025-12-22 | HY-14394 | 4,5,6,7-四溴-1H-苯并三唑 | 17374-26-4 | 10mM * 1mLin DMSO | 330 |
