90271-86-6

Basic information

• Product Name: 5-Bromo-3-cyanoindole
• Synonyms: 5-BROMO-3-CYANOINDOLE;5-BROMO-3-FLUOROINDOLE;5-Bromo-1H-indole-3-carbonitrile;5-BroMoindole-3-lindoleforMonitrile;1H-Indole-3-carbonitrile, 5-bromo-;5-Bromo-3-cyano-1H-indole
• CAS NO: 90271-86-6
• Molecular Formula: C₉H₅BrN₂
• Molecular Weight: 221.05
• Product Categories: pharmacetical;Indole;Organohalides
• Mol File: 90271-86-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 199.3 °C
• Appearance: /
• Density: 1.74 g/cm³
• Vapor Pressure: 8.44E-07mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13?+-.0.30(Predicted)
• CAS DataBase Reference: 5-Bromo-3-cyanoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-3-cyanoindole(90271-86-6)
• EPA Substance Registry System: 5-Bromo-3-cyanoindole(90271-86-6)

Safety Data

• Hazardous Substances Data: 90271-86-6(Hazardous Substances Data)

Usage

General Description

5-Bromo-3-cyanoindole is a chemical compound with the molecular formula C9H5BrN2. It is a derivative of indole and belongs to the class of organic compounds known as tryptamines. 5-Bromo-3-cyanoindole is a brominated cyanated derivative of indole, and it is commonly used as a building block in the synthesis of various pharmaceutical and biologically active compounds. Its structure features a 5-bromoindole core with a cyano group attached to the third carbon position. 5-Bromo-3-cyanoindole has also been studied for its potential applications in the fields of drug discovery and medicinal chemistry.

InChI:InChI=1/C9H5BrN2/c10-7-1-2-9-8(3-7)6(4-11)5-12-9/h1-3,5,12H

Upstream product

• 5457-28-3 3-cyano-1H-indole 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 10075-50-0 5-bromo-1H-indole 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 75-05-8 acetonitrile 
• 75-52-5 nitromethane 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 

Downstream Products

• 1071970-25-6 4-(5-bromo-3-cyanoindol-1yl)benzoic acid ethyl ester 
• 1219741-43-1 5-bromo-1-methyl-1H-indole-3-carbonitrile 

Relevant articles and documents

Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors

Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2- aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds.

1,2,4-Oxadiazole Topsentin Analogs with Antiproliferative Activity against Pancreatic Cancer Cells, Targeting GSK3β Kinase

A new series of topsentin analogs, in which the central imidazole ring of the natural lead was replaced by a 1,2,4-oxadiazole moiety, was efficiently synthesized. All derivatives were pre-screened for antiproliferative activity against the National Cancer Institute (NCI-60) cell lines panel. The five most potent compounds were further investigated in various pancreatic ductal adenocarcinoma (PDAC) cell lines, including SUIT-2, Capan-1, and Panc-1 cells, eliciting EC50 values in the micromolar and sub-micromolar range, associated with significant reduction of cell migration. These remarkable results might be explained by the effects of these new topsentin analogues on epithelial-to-mesenchymal transition markers, including SNAIL-1/2 and metalloproteinase-9. Moreover, flow cytometric analysis after Annexin V-FITC and propidium iodide staining demonstrated that these derivatives enhanced apoptosis of PDAC cells. Keeping with these data, the PathScan intracellular signaling and ELISA array revealed cleavage of caspase-3 and PARP and a significant inhibition of GSK3β phosphorylation, suggesting this kinase as a potential downstream target of our novel compounds. This was further supported by a specific assay for the evaluation of GSK3β activity, showing IC50 values for the most active compounds against this enzyme in the micromolar range.

Efficient construction of diverse 3-cyanoindoles under novel tandem catalysis

A novel and rapid construction of 3-cyanoindoles by palladium-catalyzed tandem reactions has been developed. "N-H"free unprotected, N-alkyl and N-aryl 3-cyanoindoles are obtained with good to excellent yields. The usefulness of this synthetic approach is further demonstrated by the successful synthesis of practical compounds such as the therapeutic estrogen receptor ligand A precursor. Mechanism study shows that the tandem catalysis exploits a Suzuki cross-coupling with subsequent base-induced isoxazole fragmentation, followed by the aldimine condensation.