4(二(1H-吲哚-3-基)甲基)苯酚

生物活性靶点体外研究体内研究 4(二(1H-吲哚-3-基)甲基)苯酚试剂级价格

4(二(1H-吲哚-3-基)甲基)苯酚

CAS号:151358-47-3
英文名:4-(di(1H-indol-3-yl)Methyl)phenol
中文名:4(二(1H-吲哚-3-基)甲基)苯酚
CBNumber:CB12682261
分子式:C23H18N2O
分子量:338.4
MOL File:151358-47-3.mol

4(二(1H-吲哚-3-基)甲基)苯酚化学性质

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 :Soluble in DMSO (35 mg/ml); ethanol (35 mg/ml)
形态 :solid
酸度系数(pKa) :9.98±0.26(Predicted)
颜色 :Pink
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.
InChI :1S/C23H18N2O/c26-16-11-9-15(10-12-16)23(19-13-24-21-7-3-1-5-17(19)21)20-14-25-22-8-4-2-6-18(20)22/h1-14,23-26H
InChIKey :QCPDFNWJBQMXLI-UHFFFAOYSA-N
SMILES :OC1=CC=C(C(C2=CNC3=C2C=CC=C3)C4=CNC5=C4C=CC=C5)C=C1

安全信息

WGK Germany :WGK 3
存储类别 :11 - Combustible Solids

4(二(1H-吲哚-3-基)甲基)苯酚性质、用途与生产工艺

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
Target Value
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.

生产方法

120-72-9

123-08-0

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