4(二(1H-吲哚-3-基)甲基)苯酚
| 中文名称 | 4(二(1H-吲哚-3-基)甲基)苯酚 |
|---|---|
| 中文同义词 | 4(二(1H-吲哚-3-基)甲基)苯酚;化合物DIM-C-PPHOH;DIM-C-PPHOH,NUR77拮抗剂;化合物DIM-C-PPHOH,10 MM DMSO 溶液 |
| 英文名称 | 4-(di(1H-indol-3-yl)Methyl)phenol |
| 英文同义词 | 4-(di(1H-indol-3-yl)Methyl)phenol;DIM-C-pPhOH;4-[bis(1H-indol-3-yl)methyl]phenol;C-DIM8;1,1-Bis(3'-indolyl)-1-(p-hydroxyphenyl)methane;DIM-C-pPhOH(CDIM8);Phenol, 4-(di-1H-indol-3-ylmethyl)-;inhibit,receptor,Inhibitor,β1-integrin,mTOR,cancer,DIMCpPhOH,signaling,nuclear,xenografts,Apoptosis,DIM C pPhOH,stress |
| CAS号 | 151358-47-3 |
| 分子式 | C23H18N2O |
| 分子量 | 338.4 |
| EINECS号 | |
| 相关类别 | 吲哚类 |
| Mol文件 | 151358-47-3.mol |
| 结构式 |  |
4(二(1H-吲哚-3-基)甲基)苯酚 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） |
| 形态 | 固体 |
| 酸度系数(pKa) | 9.98±0.26(Predicted) |
| 颜色 | 粉色 |
| 稳定性 | 自购买之日起 2 年内保持稳定。 DMSO 溶液可在 -20°C 下保存长达 2 个月。 |
| 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 |
| Target | Value |
|
Nur77
(786-O cells based assay) | 13.0 μM |
|
Nur77
(ACHN cells based assay) | 13.6 μM |
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. |
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. |
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
安全信息
| WGK Germany | WGK 3 |
|---|---|
| 存储类别 | 11 - 可燃固体 |
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2026/07/06 | S6799 | 4(二(1H-吲哚-3-基)甲基)苯酚 DIM-C-pPhOH | 151358-47-3 | 5mg | 770.25元 |
| 2026/07/06 | S6799 | 4(二(1H-吲哚-3-基)甲基)苯酚 DIM-C-pPhOH | 151358-47-3 | 10mM (1mL in DMSO) | 958.23元 |