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151358-47-3

中文名称 4(二(1H-吲哚-3-基)甲基)苯酚
英文名称 4-(di(1H-indol-3-yl)Methyl)phenol
CAS 151358-47-3
分子式 C23H18N2O
分子量 338.4
MOL 文件 151358-47-3.mol
更新日期 2025/07/02 16:10:15
151358-47-3 结构式 151358-47-3 结构式

基本信息

中文别名
化合物DIM-C-PPHOH
4(二(1H-吲哚-3-基)甲基)苯酚
英文别名
C-DIM8
DIM-C-pPhOH
DIM-C-pPhOH(CDIM8)
4-(di(1H-indol-3-yl)Methyl)phenol
4-[bis(1H-indol-3-yl)methyl]phenol
Phenol, 4-(di-1H-indol-3-ylmethyl)-
1,1-Bis(3'-indolyl)-1-(p-hydroxyphenyl)methane

物理化学性质

熔点122-124 °C
沸点610.2±50.0 °C(Predicted)
密度1.321±0.06 g/cm3(Predicted)
储存条件Sealed in dry,Room Temperature
溶解度溶于 DMSO (35 mg/ml);乙醇(35 毫克/毫升)
酸度系数(pKa)9.98±0.26(Predicted)
形态固体
颜色粉色
稳定性Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.

安全数据

危险性符号(GHS)GHS hazard pictograms
GHS07
警示词警告
危险性描述H302-H315-H319-H335

制备方法

方法1
吲哚

120-72-9

对羟基苯甲醛

123-08-0

4(二(1H-吲哚-3-基)甲基)苯酚

151358-47-3

通用方法:将BiVO4纳米颗粒(BiVO4-NPs,30 mg)加入至含有吲哚或2-甲基吲哚(2 mmol)与醛类化合物(1 mmol)的混合物中。在无溶剂条件下,将反应混合物于80℃搅拌反应适当时间。反应进程通过薄层色谱(TLC)监测。反应完成后,用30 mL热乙醇稀释反应混合物,通过过滤回收催化剂,并用乙醇(5 mL)洗涤。减压蒸发溶剂,剩余固体通过乙醇/水(95:5,v/v)混合溶剂重结晶,得到纯产物4-(二(1H-吲哚-3-基)甲基)苯酚。所有产物的光谱及物理数据与文献报道一致,并与按先前报道方法制备的样品相符。

参考文献:

[1] Tetrahedron Letters, 2003, vol. 44, # 9, p. 1959 - 1961

[2] Journal of Chemical Research, 2004, # 1, p. 34 - 36

[3] Monatshefte fur Chemie, 2004, vol. 135, # 10, p. 1265 - 1273

[4] RSC Advances, 2016, vol. 6, # 96, p. 93546 - 93550

[5] Synthetic Communications, 2004, vol. 34, # 3, p. 487 - 492

4(二(1H-吲哚-3-基)甲基)苯酚价格(试剂级)
报价日期产品编号产品名称CAS号包装价格
2025/05/22HY-1120554(二(1H-吲哚-3-基)甲基)苯酚
DIM-C-pPhOH
151358-47-31mg500元
2025/05/22HY-1120554(二(1H-吲哚-3-基)甲基)苯酚
DIM-C-pPhOH
151358-47-35mg750元
2025/05/22HY-1120554(二(1H-吲哚-3-基)甲基)苯酚
DIM-C-pPhOH
151358-47-310mM * 1mLin DMSO825元

常见问题列表

生物活性
DIM-C-pPhOH (C-DIM8, CDIM8)是一种 nuclear receptor 4A1 (NR4A1)(Nur77) 拮抗剂。DIM-C-pPhOH 可抑制肿瘤生长和mTOR信号传导,并诱导细胞凋亡和细胞应激。DIM-C-pPhOH 可降低细胞增殖,其对 ACHN细胞 和 786-O细胞 的IC50值分别为13.6 μM 和 13.0 μM。
靶点
TargetValue
Nur77
(786-O cells based assay)
13.0 μM
Nur77
(ACHN cells based assay)
13.6 μM
体外研究

DIM-C-pPhOH (7.5-20 μM; 24 hours; ACHN and 786-O cells) treatment significantly decreases cell proliferation.
DIM-C-pPhOH (20 μM; 24 hours; ACHN and 786-O cells) treatment induces Annexin V staining in ACHN and 786-O cells, confirming that DIM-C-pPhOH induce apoptosis, and also induces cleavage of caspases 7 and 8.
DIM-C-pPhOH (15-20 μM; 24 hours; ACHN and 786-O cells) treatment inhibits NR4A1-regulated expression of survivin, bcl-2 and EGFR in ACHN and 786-O cells. And also induces sestrin 2, activates AMPKα and inhibits activation of mTOR and downstream kinases.
DIM-C-pPhOH decreases expression of β1-integrin protein and mRNA and β1-integrin-dependent responses in MCF7, MDA-MB-231, and SKBR3 cells and also inhibits migration of the latter two cell lines.

Cell Proliferation Assay

Cell Line: ACHN and 786-O cells
Concentration: 7.5 μM, 15 μM, 20 μM
Incubation Time: 24 hours
Result: Significantly decreased cell proliferation.

Apoptosis Analysis

Cell Line: ACHN and 786-O cells
Concentration: 20 μM
Incubation Time: 24 hours
Result: Induced apoptosis in ACHN and 786-O cells.

Western Blot Analysis

Cell Line: ACHN and 786-O cells
Concentration: 15 μM, 20 μM
Incubation Time: 24 hours
Result: Inhibited NR4A1-regulated expression of survivin, bcl-2 and EGFR in ACHN and 786-O cells. And also induced sestrin 2, activated AMPKα and inhibited activation of mTOR and downstream kinases.
体内研究

DIM-C-pPhOH (30 mg/kg; oral gavage; daily; for 50 days; male athymic nude mice) treatment results in a significant inhibition of tumor growth.

Animal Model: Male athymic nude mice (aged 6-7 weeks) injected with ACHN cells
Dosage: 30 mg/kg/day
Administration: Oral gavage; daily; for 50 days
Result: Resulted in a significant inhibition of tumor growth.
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