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4-(di(1H-indol-3-yl)Methyl)phenol, also known as C-DIM 8, is a compound with the molecular formula (151358-47-3). It functions as an antagonist of the orphan nuclear receptor Nur77 (NR4A1, TR3) and has been found to possess various biological activities, making it a potential candidate for pharmaceutical applications.

151358-47-3

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151358-47-3 Usage

Uses

Used in Anticancer Applications:
In the pharmaceutical industry, 4-(di(1H-indol-3-yl)Methyl)phenol is used as an anticancer agent. It induces reactive oxygen species and ER stress in pancreatic cancer cells, leading to the inhibition of cell growth and the induction of apoptosis. 4-(di(1H-indol-3-yl)Methyl)phenol also mimics the effect of Nur77 knockdown in non-small-cell lung cancer A549 and H460 cells, further contributing to its anticancer properties.
Additionally, 4-(di(1H-indol-3-yl)Methyl)phenol inhibits the expression of β1and β3-integrin, blocking integrin-dependent breast cancer cell migration. It also decreases the expression of the histone methyltransferase G9A (EHMT2) in a variety of cancer cell lines, which may contribute to its overall anticancer effects.
Used in Drug Delivery Systems:
In the field of drug delivery, 4-(di(1H-indol-3-yl)Methyl)phenol can be employed to enhance the efficacy and bioavailability of various pharmaceutical compounds. Its ability to modulate multiple signaling pathways and inhibit the expression of key proteins involved in cancer cell growth and migration makes it a promising candidate for the development of novel drug delivery systems, potentially improving therapeutic outcomes for cancer patients.

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

Check Digit Verification of cas no

The CAS Registry Mumber 151358-47-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,1,3,5 and 8 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 151358-47:
(8*1)+(7*5)+(6*1)+(5*3)+(4*5)+(3*8)+(2*4)+(1*7)=123
123 % 10 = 3
So 151358-47-3 is a valid CAS Registry Number.

151358-47-3Relevant articles and documents

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

Heravi, Majid M.,Nahavandi, Fatemeh,Sadjadi, Samaheh,Oskooie, Hosien A.,Tajbakhsh, Mahmood

, p. 3285 - 3292 (2009)

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.

Micron particles of AlN/Al: Efficient, novel, and reusable heterogeneous catalyst for the synthesis of Bis(indolyl)methanes

Tekale, Sunil U.,Shisodia, Suresh S.,Kauthale, Sushma S.,Jadhav, Vivekanand B.,Kanhe, Nilesh S.,Bhoraskar, Sudha V.,Pawar, Rajendra P.

, p. 1849 - 1858 (2013)

The present work introduces for the first time the catalytic utility of micron particulate aluminium nitride (AlN/Al) as a novel and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes involving the electrophilic substitution of indo

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

Saffar-Teluri, Ali

, p. 1061 - 1067 (2014)

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

CuBr2-catalyzed synthesis of bis(indolyl)methanes

Mo, Li-Ping,Ma, Zi-Chuan,Zhang, Zhan-Hui

, p. 1997 - 2004 (2005)

Copper(II) bromide is found to be an efficient catalyst for the electrophilic substitution reaction of indole with aldehydes to afford the corresponding bis(indolyl)-methanes in good yields. Copyright Taylor & Francis, Inc. 1997-2004.

Ion Exchange Resin Catalyzed Condensation of Indole and Carbonyl Compounds - Synthesis of bis-Indolylmethanes

Feng, Xin-Liang,Guan, Chuan-Jin,Zhao, Cheng-Xue

, p. 487 - 492 (2004)

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

Enhanced catalytic activity of Zr(IV) complex with simple tetradentate Schiff base ligand in the clean synthesis of indole derivatives

Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Gorzin, Ghorbanali

, p. 1732 - 1736 (2011)

Zirconium (IV) tetradentate Schiff base (salphen) complex has been successfully used for efficient synthesis of wide variety of indole derivatives in EtOH as a standard green solvent under mild conditions. The investigation of turnover number and reusabil

Diindolylmethane Derivatives: Potent Agonists of the Immunostimulatory Orphan G Protein-Coupled Receptor GPR84

Pillaiyar, Thanigaimalai,K?se, Meryem,Sylvester, Katharina,Weighardt, Heike,Thimm, Dominik,Borges, Gleice,F?rster, Irmgard,Von Kügelgen, Ivar,Müller, Christa E.

, p. 3636 - 3655 (2017)

The Gi protein-coupled receptor GPR84, which is activated by (hydroxy)fatty acids, is highly expressed on immune cells. Recently, 3,3′-diindolylmethane was identified as a heterocyclic, nonlipid-like GPR84 agonist. We synthesized a broad range of diindolylmethane derivatives by condensation of indoles with formaldehyde in water under microwave irradiation. The products were evaluated at the human GPR84 in cAMP and β-arrestin assays. Structure-activity relationships (SARs) were steep. 3,3′-Diindolylmethanes bearing small lipophilic residues at the 5- and/or 7-position of the indole rings displayed the highest activity in cAMP assays, the most potent agonists being di(5-fluoro-1H-indole-3-yl)methane (38, PSB-15160, EC50 80.0 nM) and di(5,7-difluoro-1H-indole-3-yl)methane (57, PSB-16671, EC50 41.3 nM). In β-arrestin assays, SARs were different, indicating biased agonism. The new compounds were selective versus related fatty acid receptors and the arylhydrocarbon receptor. Selected compounds were further investigated and found to display an ago-allosteric mechanism of action and increased stability in comparison to the lead structure.

Facile synthesis of bis(indolyl)alkanes catalyzed by cu(clo 4)2.6h2o under solvent free conditions

Baruah, Mukulesh

, p. 461 - 463 (2011)

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.

A new catalytic method for ecofriendly synthesis of bis- and trisindolylmethanes by zirconyldodecylsulfate under mild conditions

Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Golshani, Tayebeh

, p. 535 - 539 (2009)

(Chemical Equation Presented) Zirconyldodecylsulfate (ZrO(DS)2) as a versatile Lewis acid-surfactant-combined (LASC) catalyzed ecofriendly synthesis of bis- and tris(indolyl)methanes via electrophilic substitution of indoles with carbonyl compo

An effective green and ecofriendly catalyst for synthesis of bis(indolyl)methanes as promising antimicrobial agents

Nemallapudi, Bakthavatchala Reddy,Zyryanov, Grigory V.,Avula, Balakrishna,Guda, Mallikarjuna Reddy,Gundala, Sravya

, p. 3324 - 3332 (2019)

An effective and suitable meglumine-catalyzed high-yielding process was considered and engaged for the synthesis of new bis(indolyl)methanes at ambient temperature under aqueous conditions. The catalytic reaction proceeds very smoothly. Clean reaction, ea

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