51072-85-6

Usage

Molecular weight

218.25 g/mol

Derivative of

Indole (a heterocyclic aromatic organic compound)

Usage

Building block for the synthesis of pharmaceutical compounds, precursor in the production of agrochemicals and dyes

Potential properties

Anti-cancer and anti-inflammatory

Industry

Pharmaceutical, agrochemical, and dye industries

Medicinal chemistry research

Compound of interest for its potential biological activity.

Upstream product

• 948-65-2 2-phenyl-indole 
• 66365-41-1 triphenylphosphine-thiocyanogen 
• 33842-02-3 dichloromethylenedimethyliminium chloride 
• 2973-50-4 2-aminophenylacetonitrile 
• 98-88-4 benzoyl chloride 
• 98508-69-1 2-chloro-3-phenylsulfonylindole 
• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 
• 1258597-25-9 2-phenyl-1H-indole-3-carbaldehyde O-acetyl oxime 
• 5460-84-4 2-phenyl-1H-indole-3-carbaldehyde oxime 
• 119072-55-8 tert-butylisonitrile 
• 1397290-31-1 C₁₁H₁₂FN 
• 67824-29-7 2-phenyl-4-(5-tetrazolyl)quinazoline 
• 67824-30-0 5-phenyl-[1,2,3]-triazolo[1,5-c]quinazoline 
• 107468-25-7 3-azido-2-phenyl-3-quinoline 

Relevant academic research and scientific papers

Anomalous Dehydration of 2-Phenylindole-3-carboxamide to 2-Phenylindole-3-carbonitrile by Lithium Aluminium Hydride

Steric factors have been shown to be responsible for the anomalous dehydration of 2-phenylindole-3-carboxamide (1) to 2-phenylindole-3-carbonitrile (3) by lithium aluminium hydride.This steric effect was also reflected in the reactions of 2-phenylindole (

Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions

A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It is worth noting that this method not only can afford the synthesis of indolo[2,1-a]isoquinolines but also can provide an alternative route for generating complex target structures bearing carboxylic esters.

Mn(III)-Mediated Radical Cyclization of o-Alkenyl Aromatic Isocyanides with Boronic Acids: Access to N-Unprotected 2-Aryl-3-cyanoindoles

The synthesis of N-unprotected 2-aryl-3-cyanoindoles was realized via the Mn(III)-mediated radical cascade cyclization of o-alkenyl aromatic isocyanides with boronic acids. A possible mechanism involving a sequential intermolecular radical addition, intramolecular cyclization, and cleavage of the C-C bond under mild reaction conditions is proposed. Mechanism studies show that H2O or O2 might provide the oxygen source for the elimination of benzaldehyde.

Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products

A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.

GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide

An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.

Indole-3-carbonitriles as DYRK1A inhibitors by fragment-based drug design

Dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) is a potential drug target because of its role in the development of Down syndrome and Alzheimer's disease. The selective DYRK1A inhibitor 10-iodo-11H-indolo[3, 2-c]quinoline-6-carboxy

Synthesis of 2 H-Azirines via Iodine-Mediated Oxidative Cyclization of Enamines

A facile and practical oxidative cyclization reaction of enamines to 2H-azirines has been developed, employing molecular iodine. The features of the present synthetic approach include no use of transition metals, mild reaction conditions, and simplicity o

Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.

A 3 - cyano indole synthetic method of the compound

The invention discloses a method for synthesizing a 3-cyanoindole compound and belongs to the technical field of synthetic technology. The technical solution provided by the invention is characterized that the method for synthesizing the 3-cyanoindole com

Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1

In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.