143621-35-6
143621-35-6 结构式
基本信息
M2亚基抑制剂(TRIAPINE)
2-[(3-氨基吡啶-2-基)亚甲基]氨基硫脲
PAN-811)是核糖核苷酸还原酶抑制剂,已进入各种临床实验。
3-Apct
Pan-811
Pan 811
C078157
OCX 191
CS-2006
Triapine
OCX 0191
NSC 663249
物理化学性质
安全数据
制备方法
79-19-6
143621-33-4
143621-35-6
以氨基硫脲和2-(1,3-二氧戊环基)-3-氨基吡啶（CAS:143621-33-4）为原料合成[(3-氨基吡啶-2-基)亚甲基氨基]硫脲的一般步骤： 实施例VII：向2-(1,3-二氧戊环基)-3-氨基吡啶（0.80 g，4.8 mmol）溶于10 mL乙醇、8 mL水和2 mL浓盐酸的溶液中加入氨基硫脲（0.48 g，5.3 mmol）。将反应混合物于室温搅拌过夜，随后回流1小时。冷却后过滤，得到粗制的黄色盐酸盐。将该盐酸盐溶于50 mL热水中，过滤。向热的滤液中加入10 mL 5%碳酸氢钠溶液。混合物于室温搅拌1小时，过滤，依次用水和乙醇洗涤，得到3-氨基-2-甲酰基吡啶缩氨基硫脲。产量：0.72 g（77%）；熔点：240-241°C。质谱（MS）m/e 194（M+）；1H NMR（90 MHz，DMSO-d6）δ 6.48（br s，2H，3-NH2，可交换于D2O），7.12（m，2H，4-H和6-H），7.83（dd，1H，5-H），8.10（br s，2H，CSNH2，可交换于D2O），8.10（s，1H，2-CH），10.95（s，1H，NNH，可交换于D2O）。元素分析（C7H9N5S）符合C、H、N的理论值。
参考文献：
[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 20, p. 3672 - 3677
[2] Patent: US5281715, 1994, A
| 报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
| 2025/05/22 | HY-10082 | [(3-氨基吡啶-2-基)亚甲基氨基]硫脲 3-AP | 143621-35-6 | 5 mg | 520元 |
| 2025/05/22 | HY-10082 | [(3-氨基吡啶-2-基)亚甲基氨基]硫脲 3-AP | 143621-35-6 | 10 mM * 1 mLin DMSO | 572元 |
| 2025/05/22 | HY-10082 | [(3-氨基吡啶-2-基)亚甲基氨基]硫脲 3-AP | 143621-35-6 | 10 mg | 820元 |
常见问题列表
Ribonucleotide reductase (RR)
3-AP (Triapine) is a potent derivative of α-heterocyclic carboxaldehyde thiosemicarbazone (HCT) that inhibits hRRM2 and p53R2 isoforms of the M2 subunit. 3-AP (Triapine) is thought to inhibit ribonucleotide reductase through its preformed iron chelate, rather than directly by removing iron from the active site. In cells containing less topoisomerase IIα fewer DNA strand breaks will be produced, and thus topoisomerase II poisons will be less inhibitory in the K/VP.5 cell line. The IC 50 s for Dp44mT growth inhibition are 48±9 nM and 60±12 nM, for K562 and K/VP.5 cells, respectively. The IC 50 s for 3-AP growth inhibition are 476±39 nM and 661±69 nM for K562 and K/VP.5 cells, respectively. PKIH and DpT Fe chelators show high antiproliferative activity against a range of tumor cell lines. Dp44mT shows the greatest antitumor efficacy with an IC 50 that ranged from 0.005 to 0.4 μM. The average IC 50 of Dp44mT over 28 cell types is 0.03±0.01 μM, which is significantly lower than that of 3-AP (Triapine; average IC 50 : 1.41±0.37 μM).
3-AP (Triapine) causes a significant increase (1.7-fold) in splenic weight when expressed as a percentage of total body weight (1.02±0.06%; n=25) compared with control mice (0.6±0.03%; n=27). In the long-term group, a significant increase in heart weight is observed after Dp44mT (0.4 mg/kg per day) (0.8±0.06%; n=4) compared with control mice (0.5±0.01%; n=6). A significant decrease in the expression of Ndrg1, TfR1, and VEGF1 in the liver is noted for Dp44mT- and 3-AP (12 mg/kg per day)-treated animals. The decreased expression could be related to the increased liver Fe in both Dp44mT- and 3-AP-treated mice.