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151358-47-3

中文名稱 4(二(1H-吲哚-3-基)甲基)苯酚
英文名稱 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 結(jié)構(gòu)式 151358-47-3 結(jié)構(gòu)式

基本信息

中文別名
化合物DIM-C-PPHOH
4(二(1H-吲哚-3-基)甲基)苯酚
英文別名
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

物理化學(xué)性質(zhì)

熔點(diǎn)122-124 °C
沸點(diǎn)610.2±50.0 °C(Predicted)
密度1.321±0.06 g/cm3(Predicted)
儲存條件Sealed in dry,Room Temperature
溶解度溶于 DMSO (35 mg/ml);乙醇(35 毫克/毫升)
酸度系數(shù)(pKa)9.98±0.26(Predicted)
形態(tài)固體
顏色粉色
穩(wěn)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.

安全數(shù)據(jù)

危險性符號(GHS)有害 (GHS07)
GHS07
警示詞警告
危險性描述H302-H315-H319-H335

制備方法

方法1
吲哚

120-72-9

對羥基苯甲醛

123-08-0

4(二(1H-吲哚-3-基)甲基)苯酚

151358-47-3

通用方法:將BiVO4納米顆粒(BiVO4-NPs,30 mg)加入至含有吲哚或2-甲基吲哚(2 mmol)與醛類化合物(1 mmol)的混合物中。在無溶劑條件下,將反應(yīng)混合物于80℃攪拌反應(yīng)適當(dāng)時間。反應(yīng)進(jìn)程通過薄層色譜(TLC)監(jiān)測。反應(yīng)完成后,用30 mL熱乙醇稀釋反應(yīng)混合物,通過過濾回收催化劑,并用乙醇(5 mL)洗滌。減壓蒸發(fā)溶劑,剩余固體通過乙醇/水(95:5,v/v)混合溶劑重結(jié)晶,得到純產(chǎn)物4-(二(1H-吲哚-3-基)甲基)苯酚。所有產(chǎn)物的光譜及物理數(shù)據(jù)與文獻(xiàn)報道一致,并與按先前報道方法制備的樣品相符。

參考文獻(xiàn):

[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)苯酚價格(試劑級)
報價日期產(chǎn)品編號產(chǎn)品名稱CAS號包裝價格
2026/03/03S67994(二(1H-吲哚-3-基)甲基)苯酚
DIM-C-pPhOH
151358-47-35mg770.25元
2026/03/03S67994(二(1H-吲哚-3-基)甲基)苯酚
DIM-C-pPhOH
151358-47-310mM (1mL in DMSO)958.23元
2026/03/03S67994(二(1H-吲哚-3-基)甲基)苯酚
DIM-C-pPhOH
151358-47-325mg1975.48元

常見問題列表

生物活性
DIM-C-pPhOH (C-DIM8, CDIM8)是一種 nuclear receptor 4A1 (NR4A1)(Nur77) 拮抗劑。DIM-C-pPhOH 可抑制腫瘤生長和mTOR信號傳導(dǎo),并誘導(dǎo)細(xì)胞凋亡和細(xì)胞應(yīng)激。DIM-C-pPhOH 可降低細(xì)胞增殖,其對 ACHN細(xì)胞 和 786-O細(xì)胞 的IC50值分別為13.6 μM 和 13.0 μM。
靶點(diǎn)
TargetValue
Nur77
(786-O cells based assay)
13.0 μM
Nur77
(ACHN cells based assay)
13.6 μM
體外研究

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.
體內(nèi)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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