178946-89-9

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References

1) Inamoto et al. (2008), 1,1-Bis(3’-indolyl)-1-(p-chlorophenyl)methane activates the orphan nuclear receptor Nurr1 and inhibits bladder cancer growth; Mol Cancer Ther., 7 3825 2) Li et al. (2012), Structure-dependent activation of NR4A2 (Nurr1) by 1,1-bis(3’-indoyl)-1-(aromatic)methane analogs in pancreatic cancer cells; Biochem. Pharmacol., 83 1445 3) De Miranda et al. (2015), The Nurr1 Activator 1,1-Bis(3’-Indolyl)-1-(p-chlorophenyl)Methane blocks Inflammatory Gene Expression in BV-2 Microglial Cells by Inhibiting Nuclear Factor kB; Mol. Pharmacol., 87 1021 4) De Miranda et al. (2013), Neuroprotective efficacy and pharmokinetic behavior of novel anti-inflammatory para phenyl substituted diindolylmethanes ina a mouse model of Parkinson’s disease; J. Pharmacol. Exp. Ther., 345 125

Upstream product

• 120-72-9 indole 
• 104-88-1 4-chlorobenzaldehyde 
• 1613-95-2 (E)-1-(4-chlorophenyl)-N-phenylmethanimine 
• 1751-80-0 (E)-4-chloro-N-(4-chlorobenzylidene)benzenamine 
• 2362-79-0 N-(4-chlorobenzylidene)aniline 
• 33442-36-3 (E)-1-(4-chlorophenyl)-N-(p-tolyl)methanimine 
• 57270-86-7 5-(4-chlorobenzylidene)-1,3-dimethylbarbituric acid 
• 769-42-6 1,3-dimethylbarbituric acid 
• 873-76-7 para-Chlorobenzyl alcohol 
• 778577-38-1 N-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)methyl)toluenesulfonamide 
• 3157-65-1 N-(p-chlorobenzylidene)-p-toluenesulfonamide 
• 104-86-9 4-chlorobenzylamine 
• 1426243-80-2 2-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)methyl)-1,3-diphenylpropane-1,3-dione 
• 52670-38-9 2-ethynylaniline 

Downstream Products

• 120-72-9 indole 

Relevant academic research and scientific papers

A convenient method of synthesis of bisindolylmethanes: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases

Anhydrous indium trichloride (InCl3) is found to catalyze the electrophilic substitution reaction of indole with aromatic aldehydes and Schiff's bases which resulted in an efficient synthesis of bis- indolylmethanes in good to excellent yield.

Potassium hydrogen sulfate-catalyzed reactions of indoles: A mild, expedient synthesis of bis-indolylmethanes

Biologically important bis-indolylmethanes and their derivatives were prepared in good yields by the electrophilic substitution of indole with aldehydes catalyzed by potassium hydrogen sulfate.

Preparation of bisindolylalkanes from N-tert-butanesulfinyl aldimines

A series of bisindolylalkanes were synthesized by nucleophilic addition reactions of indole with N-tert-butanesulfinyl aldimines in good to excellent yields catalyzed by either iodine, potassium hydrogen sulfate and amberlyst.

Enantioselective Friedel-Crafts reaction of indoles with carbonyl compounds catalyzed by bifunctional cinchona alkaloids

In this communication, we report an efficient asymmetric Friedel-Crafts reaction that, unprecedently, is applicable to a wide range of both indoles and carbonyls. The use of a readily accessible catalyst in combination with a high enantioselectivity that is insensitive to reaction concentration, temperature, air, and moisture should allow this reaction to provide useful enantioselective access to new chiral indole derivatives.

Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines

Dy(OTf)3 immobilized in ionic liquids was found to be an efficient catalytic system for the reactions of indole with aldehydes/ketones or imines. Enhanced activity was observed. The use of ionic liquids as the reaction media allows facile separ

A new approach for the synthesis of bisindoles through agOTf as catalyst

A novel approach for the catalyzed formation of bisindolylmethane derivatives (BIMs) is described. This methodology is the unique example where AgOTf has been successfully used for the activation of aldehydes, giving easy access to a broad range of bisind

[Fe(III)(salophen)]Cl in Molten Tetrabutylammonium Bromide as a New Homogeneous Catalytic System for the Electrophilic Reaction of Indole with Carbonyl Compounds

[Fe(III)(salophen)]Cl in molten tetrabutylammonium bromide was used as a cost effective and efficient catalytic system for the electrophilic reaction of indole with carbonyl compounds. The remarkable features of this new procedure are high conversions, sh

Efficient Synthesis of Bis(indolyl)methanes Catalyzed by Lewis Acids in Ionic Liquids

Efficient electrophilic substitution reactions of indoles with various aldehydes proceed smoothly in ionic liquids using Lewis acids, In(OTf) 3, YbCl3, InCl3, BiCl3, and ZnCl2, to afford the correspon

A simple, efficient and green procedure for the synthesis of bis-indolyl methanes in 1,1,1,3,3,3-hexafluoro-2-propanol

A simple, inexpensive, environmentally friendly and efficient route for the synthesis of bis-indolyl methanes derivatives by the reaction of indole or N-methyl indole with aldehydes using hexafluoroisopropanol as a solvent is described. The solvent (HFIP)

Pentafluorophenylammonium triflate as an efficient, environmentally friendly and novel organocatalyst for synthesis of bis-indolyl methane derivatives

A simple, inexpensive, environmentally friendly and efficient route for the synthesis of bis-indolyl methane derivatives by the reaction of indole or N-methyl indole with aldehydes using pentafluorophenylammonium triflate (PFPAT) as a catalyst is describe