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17374-26-4

中文名稱 4,5,6,7-四溴-1H-苯并三唑
英文名稱 4,5,6,7-TETRABROMOBENZOTRIAZOLE
CAS 17374-26-4
分子式 C6HBr4N3
分子量 434.71
MOL 文件 17374-26-4.mol
更新日期 2025/07/11 11:34:46
17374-26-4 結(jié)構(gòu)式 17374-26-4 結(jié)構(gòu)式

基本信息

中文別名
7-四溴苯并三唑
4,5,6,7-四溴苯并三唑
4,5,6,7-四溴苯基三唑
4,5,6,7-四溴-1H-苯并三唑
TBB(4,5,6,7-四溴-1H-苯并三唑)
英文別名
TBB
TBBT
NSC 231634
CK2 INHIBITOR
TBB(NSC 231634)
TBB (enzyMe inhibitor)
4,5,6,7-Tetrabromotriazole
CASEIN KINASE II INHIBITOR I
4,5,6,7-TETRABROMOBENZOTRIAZOLE
CASEIN KINASE II INHIBITOR *TBB**
所屬類別
生物化工:激動(dòng)劑抑制劑

物理化學(xué)性質(zhì)

熔點(diǎn)262-266°C
沸點(diǎn)552.5±45.0 °C(Predicted)
密度2.840±0.06 g/cm3(Predicted)
儲(chǔ)存條件2-8°C
儲(chǔ)存條件2-8°C
溶解度DMSO: 28 mg/mL
溶解度在DMSO中的溶解度為28 毫克/毫升
酸度系數(shù)(pKa)3.87±0.40(Predicted)
形態(tài)solid
顏色white
最大波長(λmax)300nm(MeOH)(lit.)

安全數(shù)據(jù)

危險(xiǎn)性符號(hào)(GHS)GHS hazard pictograms
GHS07
警示詞警告
危險(xiǎn)性描述H302-H315-H319-H335
WGK Germany3
WGK Germany3
海關(guān)編碼29349990

常見問題列表

合成方法
苯并三氮唑

95-14-7

4,5,6,7-四溴-1H-苯并三唑

17374-26-4

采用文獻(xiàn)[39]報(bào)道的方法進(jìn)行適當(dāng)修改。將1H-苯并三唑(32,3g)溶解于69% HNO3(50mL)與100% HNO3(3mL)的混合溶液中。隨后,將溶液加熱至80℃,并在1小時(shí)內(nèi)緩慢滴加Br2(6當(dāng)量)。反應(yīng)混合物在60℃下劇烈攪拌48小時(shí)后,冷卻至室溫。在氮?dú)獗Wo(hù)下,通過20% Na2S2O5水溶液(100mL)捕集并除去未反應(yīng)的Br2。接著,將反應(yīng)混合物倒入冰冷的H2O(200mL)與飽和Na2S2O5水溶液(10mL)的混合液中。過濾收集生成的橙色沉淀,并依次用H2O(50mL)和EtOH(50mL)洗滌。粗產(chǎn)物通過熱MeOH(50mL)多次洗滌純化,得到白色固體4,5,6,7-四溴-1H-苯并三唑(TBBt,34,7.45g,17.14mmol,產(chǎn)率68%)。通過高分辨率質(zhì)譜(HRMS)確認(rèn)產(chǎn)物結(jié)構(gòu)。1H NMR、13C NMR及熔點(diǎn)數(shù)據(jù)與文獻(xiàn)報(bào)道一致。TBBt 34的性質(zhì)如下:白色固體;熔點(diǎn)264-266℃(MeOH)[文獻(xiàn)值:262-266℃(乙酸)][89];HRMS(ESI-TOF)m/z:[M + H]+ C9H7Br5N3+ m/z計(jì)算值:435.6941,實(shí)測值:435.6629。

參考文獻(xiàn):

[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

生物活性
TBB是可滲透細(xì)胞,ATP競爭型的 CK2 抑制劑,抑制大鼠肝臟CK2的 IC50 值為0.15 μM。
靶點(diǎn)

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 )

體外研究

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.

體內(nèi)研究

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).

4,5,6,7-四溴-1H-苯并三唑價(jià)格(試劑級(jí))
報(bào)價(jià)日期產(chǎn)品編號(hào)產(chǎn)品名稱CAS號(hào)包裝價(jià)格
2025/05/22HY-143944,5,6,7-四溴-1H-苯并三唑
TBB
17374-26-45 mg300元
2025/05/22HY-143944,5,6,7-四溴-1H-苯并三唑
TBB
17374-26-410mM * 1mLin DMSO330元
2025/05/22HY-143944,5,6,7-四溴-1H-苯并三唑
TBB
17374-26-410mg400元
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