151358-47-3

Basic information

• Product Name: 4-(di(1H-indol-3-yl)Methyl)phenol
• Synonyms: 4-(di(1H-indol-3-yl)Methyl)phenol;DIM-C-pPhOH;4-[bis(1H-indol-3-yl)methyl]phenol
• CAS NO: 151358-47-3
• Molecular Formula: C₂₃H₁₈N₂O
• Molecular Weight: 338.40182
• EINECS: -0
• Mol File: 151358-47-3.mol
• Article Data: 110

Chemical Properties

• Melting Point: 122-124 °C
• Boiling Point: 610.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.321±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in DMSO (35 mg/ml); ethanol (35 mg/ml)
• PKA: 9.98±0.26(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: 4-(di(1H-indol-3-yl)Methyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(di(1H-indol-3-yl)Methyl)phenol(151358-47-3)
• EPA Substance Registry System: 4-(di(1H-indol-3-yl)Methyl)phenol(151358-47-3)

Safety Data

• Hazardous Substances Data: 151358-47-3(Hazardous Substances Data)

Usage

Description

C-DIM 8 (151358-47-3) is an antagonist of the orphan nuclear receptor Nur77 (NR4A1, TR3).1 Induces reactive oxygen species and ER stress in pancreatic cancer cells.2 C-DIM 8 mimics the effect of Nur77 knockdown in non-small-cell lung cancer A549 and H460 cells, inhibiting cell growth and inducing apoptosis which was accompanied by decreased expression of survivin and inhibition of mTORC1 signaling.3 Inhibits the expression of β1- and β3-integrin and blocks integrin-dependent breast cancer cell migration.4 Decreases expression of the histone methyltransferase G9A (EHMT2) in a variety of cancer cell lines.5

References

Chintharlapalli et al. (2005), Activation of Nur77 by selected 1,1-Bis(3’-indolyl)-1-(p-substituted phenyl)methanes induces apoptosis through nuclear pathways; J. Biol. Chem., 280 24903 Lee et al. (2014), The orphan nuclear receptor NR4A1 (Nur77) regulates oxidative and endoplasmic reticulum stress in pancreatic cancer cells; Mol. Cancer Res., 12 527 Lee et al. (2012), The nuclear receptor TR3 regulates mTORC1 signaling in lung cancer cells expressing wild-type p53; Oncogene, 31 3265 Hedrick et al. (2016), NR4A1 Antagonists Inhibit ?1-Integrin-Dependent Breast Cancer Cell Migration; Mol. Cell. Biol., 36 1383 Shrestha et al. (2021), The Histone Methyltransferase Gene G9A Is Regulated by Nuclear Receptor 4A1 in Alveolar Rhabdomyosarcoma Cells; Mol. Cancer Ther. 20 612

Upstream product

• 120-72-9 indole 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-61-8 N-methylaniline 
• 16435-03-3 4-((2-phenylhydrazono)methyl)phenol 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 100-51-6 benzyl alcohol 
• 696-60-6 4-aminomethylphenol 
• 3246-66-0 4-[(4-nitro-phenylimino)-methyl]-phenol 
• 1689-73-2 N-(p-hydroxybenzylidene)aniline 
• 89-95-2 2-methyl-benzyl alcohol 
• 3369-35-5 4-[(4-chloro-phenylimino)-methyl]-phenol 

Downstream Products

• 1370262-26-2 4-(di(1H-indol-3-yl)methyl)phenyl 4-acetamidobenzenesulfonate 
• 1370262-23-9 4-(di(1H-indol-3-yl)methyl)phenyl 4-methoxybenzenesulfonate 
• 1370262-22-8 4-(di(1H-indol-3-yl)methyl)phenyl 4-methylbenzenesulfonate 
• 1370262-25-1 4-(di(1H-indol-3-yl)methyl)phenyl 4-chlorobenzenesulfonate 
• 1370262-24-0 4-(di(1H-indol-3-yl)methyl)phenyl 4-fluorobenzenesulfonate 
• 936016-49-8 C₂₃H₁₆N₂O 
• 120-72-9 indole 

Relevant articles and documents

Convenient synthesis of bis(indol)alkanes by niobium(V) chloride

Bis(indolyl)alkanes have been synthesized in excellent yields in the presence of a catalytic amount of niobium(V) chloride under solvent-free conditions. Copyright Taylor & Francis Group, LLC.

Boron trifluoride supported on nano-SiO2: An efficient and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes and oxindole derivatives

Boron trifluoride supported on nano-SiO2 was used as an efficient and heterogeneous catalyst for the electrophilic substitution reaction of indole with various aromatic aldehydes and isatins in methanol to afford the corresponding bis(indolyl)m

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The condensation reactions of indole with some carbonyl compounds were found to be catalyzed effectively by ion exchange resins under mild conditions.

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Copper perchlorate hexahydrate is found to be an efficient catalyst for the electrophilic substitution of indole with carbonyl compounds to prepare bis(indolyl)methane derivatives without solvent in excellent yield at room temperature.

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Bis-indolylation of aldehydes and ketones using silica-supported FeCl3: Molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites

We report herein an operationally simple, efficient and versatile procedure for the synthesis of bis-indolylmethanes via the reaction of indoles with aldehydes or ketones in the presence of silica-supported ferric chloride under grindstone conditions. The prepared supported catalyst was characterized by SEM and EDX spectroscopy. The present protocol has several advantages such as shorter reaction time, high yield, avoidance of using harmful organic solvents during the reaction and tolerance of a wide range of functional groups. Molecular docking studies targeted toward the binding site of SARS-CoV-2 main protease (3CLpro or Mpro) enzymes were investigated with the synthesized bis-indoles. Our study revealed that some of the synthesized compounds have potentiality to inhibit the SARS-CoV-2 Mpro enzyme by interacting with key amino acid residues of the active sites via hydrophobic as well as hydrogen bonding interactions.

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