354786-65-5

Upstream product

• 120-72-9 indole 
• 121-33-5 vanillin 
• 58285-74-8 4-chloro-N-(4-hydroxy-3-methoxybenzylidene)aniline 
• 58285-75-9 N-(4-hydroxy-3-methoxybenzylidene)-4-nitroaniline 

Downstream Products

• 120-72-9 indole 

Relevant academic research and scientific papers

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.

Enzymatic approach to cascade synthesis of bis(indolyl)methanes in pure water

A mild, efficient, and green protocol was developed for the synthesis of bis(indolyl)methanes catalyzed by lipase TLIM through the cascade reactions of indole with aldehydes in pure water. This methodology offers many superiorities such as excellent yields, wide substrate range, simple procedure, reusable and minimal amount of catalyst, and the ability to be scaled up.

Towards breast cancer targeting: Synthesis of tetrahydroindolocarbazoles, antibreast cancer evaluation, uPA inhibition, molecular genetic and molecular modelling studies

A series of some new tetrahydroindolocarbazole derivatives has been synthesized. The structure of the synthesized compounds has been confirmed by different spectroscopic techniques such as IR, NMR, elemental analysis and mass spectrometry. The target compounds were evaluated for their antitumor activity against breast cancer cell line MCF-7, their GI% and their LC50 have been determined. Six of the synthesized compounds exhibited GI% values against MCF-7 cell lines exceeding 70% ranging from 71.9 to 85.0% in addition that compound 11 expressed GI% values of 99.9% and considered the most active derivatives among the synthesized ones. Compound 11 showed a remarkable decrease of u PA level to 3.5 ng/ml compared to DOX. Compound 5, 11 and 15 showed significant decrease in expression of MTAP and CDKN2A, in addition to a remarkable decrease in DNA damage comet assay method. Molecular modeling studies were performed to interpretate the behavior of active ligands as uPA inhibitors.

A simple and efficient supramolecular chemistry approach for synthesis of bis(indolyl)methanes using aqueous β -cyclodextrin as green promoter host

Background: In the recent years, various bis-heterocyclic compounds are reported for their varied biological activities. Bis(indolyl)methanes and its derivatives are commonly present in over 3000 natural isolates and reported for its broad spectrum of bio

Synthesis, anti-methicillin-resistant S. aureus (MRSA) evaluation, quantitative structure-activity relationship and molecular modeling studies of some novel bis-indoles as prospective MRSA pyruvate kinase

Background: MRSA is a gram positive pathogen resistant to methicillin and other betalactam antibiotics, including penicillin, oxacillin, and declooxacillin. Statistical data suggest that as many as 19,000 people per year die from MRSA in the USA. Methods:

Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles

Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields. A total of 43 substrates was employed, giving 33 bisindoles, 3 trisindoles, and one 2:2 product; seventeen of these are new. The best results were obtained from heating ethanolic suspensions, with Fe2(SO4)3·xH2O loaded at 60 mg per mmol of electrophiles. The reaction times were typically 1–4 h, while hindered electrophiles required 8–24 h. These conditions were strong enough to promote 2:1 condensation of indole with substrates without forming higher-order byproducts, with few exceptions. This strategy features tolerance by the catalyst of a wide range of functional groups, readily available starting materials, simple operation, mild reaction conditions, and is environmentally friendly.

Synthesis, antibacterial and anti-inflammatory activity of bis(indolyl)methanes

A series of bioactive bis(indolyl)methanes are synthesized by one-pot green reaction of indole with various substituted aldehydes by microwave irradiation under solvent free conditions. The antibacterial activity against Staphylococcus aureus and anti-inf

Triethylbenzylammonium chloride as a useful and efficient catalyst for the alkylation of indole/substituted indoles in water: A comparative study between conventional and microwave irradiation

A green and facile method for the alkylation of indole/substituted indole in water using a phase Transfer catalyst (Triethylbenzylammonium Chloride, TEBA) to synthesise bis-indolyl methanes (BIMs) and Michael addition of indole to α,β-unsaturated carbonyl compounds is reported. The substitution of indoles occurred exclusively at the 3-position and products of N-alkylation has not been observed. However, for 3-substituted indoles, reactions were found to occur at the 2-position. A comparative study between conventional heating and microwave irradiation has also been reported. A comparative study between conventional heating and microwave irradiation for the alkylation of indole/substituted indole in water using a phase transfer catalyst (Triethylbenzylammonium Chloride, TEBA) to synthesise bis-indolyl methanes (BIMs) and Michael addition of indole to α, β-unsaturated carbonyl compounds is reported.

Ag nanoparticles: An efficient and versatile reagent for synthesis of bis(indolyl)methanes

Ag nanoparticles are 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. The remarkable features of this new procedure are high conversions

α-chymotrypsin-catalyzed synthesis of bis(indolyl)alkanes in water

A novel methodology for the synthesis of bis(indolyl)methanes by the reaction of aromatic aldehydes and indole in water has been developed, and a series of desired products were obtained in moderate to excellent yields (from 65% to 97%) using 1.2 mg/mL α-