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176957-55-4

中文名称 (2E,5E)-2,5-二(2-噻吩基亚甲基)环戊酮
英文名称 Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-
CAS 176957-55-4
分子式 C15H12OS2
分子量 272.39
MOL 文件 176957-55-4.mol
更新日期 2023/11/10 17:20:56
176957-55-4 结构式 176957-55-4 结构式

基本信息

中文别名
PPM1D抑制剂(CCT007093)
(2E,5E)-2,5-二(2-噻吩基亚甲基)环戊酮
英文别名
CS-1839
CCTOO7093
CCT007093
CCT-007093
CCT 007093
CCT007093
2,5-Bis(2-thienylmethylene)-cyclopentanone
(2E,5E)-2,5-Bis(2-thienylmethylene)cyclopentanone
2,5-bis(2-thienylMethylene)-, (E,E)-Cyclopentanone
Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-
(2E,5E)-2,5-Bis(thiophen-2-ylmethylene)cyclopentanone
Cyclopentanone, 2,5-bis(2-thienylmethylene)-, (2E,5E)-
所属类别
生物化工:激动剂抑制剂

物理化学性质

熔点222-223℃
储存条件2-8°C
溶解度二甲基亚砜:>3mg/mL
形态粉末,黄色
敏感性感光

安全数据

危险性符号(GHS)
GHS07
警示词警告
危险性描述H315-H319-H335
危险品标志Xi
危险类别码36/37/38
安全说明26
WGK Germany3

常见问题列表

简介

环戊酮曼尼希碱类化合物是由天然萜类化合物进行结构改造而设计合成的一类具有抗炎活性的化合物。构效关系研究显示二(2-噻吩基亚甲基)环戊酮曼尼希碱类化合物抗炎活性较强。(2E,5E)-2,5-二(2-噻吩基亚甲基)环戊酮是其中代表性化合物。

合成方法
以2-噻吩甲醛及环戊酮或N-环戊烯基吗啉为起始物料,经曼尼希反应制备得到目标化合物(2E,5E)-2,5-二(2-噻吩基亚甲基)环戊酮。其合成反应式如下图:

176957-55-4的合成

生物活性
CCT007093 是有效的蛋白磷酸酶 1D (PPM1D Wip1) 的抑制剂。Wip1 的抑制可激活mTORC1 通路,增强肝切除手术后肝细胞的增殖。
体外研究

CCT007093 (25 or 50 µM, 8 h) significantly increases the phosphorylation levels of mTOR at Ser2448, Ser2481 and Ser2159, and the phosphorylation levels of p70S6K (Thr389) and S6 (Ser235/236) are also up-regulated in transfected HEK293T cell line.
CCT007093 shows specificity for MCF-7 cells, reducing viability by 40% after 2 days with no observable effect on the growth of HeLa cells.
CCT007093 induces P38 phosphorylation at 4 h post exposure in MCF-7 cells (sensitive to PPM1D inhibition), and does not induce P38 phosphorylation in HeLa cells (relatively resistant to PPM1D inhibition).

Western Blot Analysis

Cell Line: HEK293T cell line.
Concentration: 25 or 50 µM.
Incubation Time: 8 h.
Result: The phosphorylation levels of mTOR at Ser2448, Ser2481 and Ser2159 were all significantly increased [1] .
The phosphorylation levels of p70S6K (Thr389) and S6 (Ser235/236) were also up-regulated [1] .
体内研究

CCT007093 (6.4 mg/kg) enhances liver regeneration and increases the survival rate of mice following major hepatectomy.

Animal Model: Wild-type mice.
Dosage: 3.2 and 6.4 mg/kg.
Administration: Injected intraperitoneally 4 times (mice were sacrificed at 36 h post-PH).
Result: Significantly improved survival in mice following major hepatectomy (80% hepatectomy).
The level of PCNA was also significantly increased in the liver of CCT007093-treated mice at 36h, 48h and 72h post-PH.
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