460746-46-7

Basic information

• Product Name: (R)-4-(2-(2-(2-METHYLPYRROLIDIN-1-YL)ETHYL)BENZOFURAN-5-YL)BENZONITRILE
• Synonyms: (R)-4-(2-(2-(2-METHYLPYRROLIDIN-1-YL)ETHYL)BENZOFURAN-5-YL)BENZONITRILE;ABT 239;4-(2-{2-[(2R)-2-Methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile;(R)-4-(2-(2-(2-Methylpyrrolidin-1-yl)- ethyl)benzofuran-5-yl)benzonitril;(R)-4-[2-[2-(2-Methylpyrrolidinyl)ethyl]benzofuran-5-yl]benzonitrile
• CAS NO: 460746-46-7
• Molecular Formula: C₂₂H₂₂N₂O
• Molecular Weight: 330.429
• Mol File: 460746-46-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 493.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 10.13±0.40(Predicted)
• CAS DataBase Reference: (R)-4-(2-(2-(2-METHYLPYRROLIDIN-1-YL)ETHYL)BENZOFURAN-5-YL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(2-(2-(2-METHYLPYRROLIDIN-1-YL)ETHYL)BENZOFURAN-5-YL)BENZONITRILE(460746-46-7)
• EPA Substance Registry System: (R)-4-(2-(2-(2-METHYLPYRROLIDIN-1-YL)ETHYL)BENZOFURAN-5-YL)BENZONITRILE(460746-46-7)

Safety Data

• Hazardous Substances Data: 460746-46-7(Hazardous Substances Data)

Usage

General Description

The chemical (R)-4-(2-(2-(2-Methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)benzonitrile is a complex compound with a chemical structure consisting of a benzofuran ring attached to a benzene ring with a nitrile group. The compound also contains a methylpyrrolidin-1-yl group and an ethyl group, which are both connected to the benzofuran ring. This chemical may have potential applications in pharmaceutical research and drug development due to its unique structure and potential biological activities. The compound's stereochemistry is specified as "(R)", indicating the configuration of its chiral center. Further research may be needed to fully understand the properties and potential uses of this chemical.

Upstream product

• 670342-24-2 toluene-4-sulfonic acid 2-[5-(4-cyano-phenyl)benzofuran-2-yl]ethyl ester 
• 765-38-8 2-methyl-1-pyrrolidine 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 117607-12-2 (R)-2-methyl-1-pyrrolidinecarboxylic acid phenylmethyl ester 
• 61350-66-1 (S)-2-(chloromethyl)-1-pyrrolidinecarboxylic acid phenylmethyl ester 
• 460746-48-9 4-[2-(2-hydroxyethyl)-1-benzofuran-5-yl]benzonitrile 
• 460746-47-8 4'-hydroxy-3'-iodo[1,1'-biphenyl]-4-carbonitrile 
• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 
• 338945-22-5 (S)-2-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 157007-54-0 2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 460747-73-3 (R)-1-(but-3-yn-1-yl)-2-methylpyrrolidine 
• 117607-13-3 (R)-2-methylpyrrolidine hydrobromide 

Downstream Products

• 460749-34-2 4-(2-{2-[(2R)-2-methyl-5-oxo-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile 
• 460747-88-0 4-(3-bromo-2-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-1-benzofuran-5-yl)benzonitrile 
• 460748-72-5 4-(3-acetyl-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile 
• 460748-71-4 4-{2-[2-((R)-2-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}benzonitrile L-tartrate 
• 460747-92-6 4-(3-(2-formyl-thien-3-yl)-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile 

Relevant articles and documents

A facile and scaleable synthesis of ABT-239, a benzofuranoid H3 antagonist

A facile and scaleable synthesis of a potent and selective histamine H 3 receptor antagonist, ABT-239 (1), was developed starting from commercially available 4′-hydroxy-biphenyl-4-carbonitrile (2). The synthesis comprised four chemical steps and a salt formation step with an overall yield of 40%. A highly selective monoiodination of a phenol was developed and used to prepare iodophenol (3b) in near quantitative yield using NIS in AcOH in the presence of a small amount of H2SO4. A Pd-catalyzed cross coupling reaction of the iodophenols (3b) with butyn-3-ol (4a) provided benzofuran (5) in one step in >80% yield, en route to 1. The new process required no chromatographic purification throughout the synthesis and was successfully demonstrated on scale-up to prepare 1.7 kg of the target ABT-239 (1).

4-(2-[2-(2(R)-Methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention

H3 receptor antagonists based on a 2-aminoethylbenzofuran skeleton have been discovered, which are potent in vitro at human and rat H 3 receptors, with Ki values of 0.1-5.8 nM. Analogues were discovered with potent (0.01-1 mg/kg) cognition and attention enhancing properties in animal models. One compound in particular, 4-(2-[2-(2(R)- methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile (ABT-239), combined potent and selective H3 receptor antagonism and excellent pharmacokinetic and metabolic properties across species, with full efficacy in two behavioral models: a five-trial inhibitory avoidance acquisition model in rat pups at 0.1 mg/kg and a social recognition memory model in adult rats at 0.01 mg/kg. Furthermore, this compound did not stimulate locomotor activity and showed high selectivity for the induction of behavioral efficacy versus central nervous system based side effects. The potency and selectivity of this compound and of analogues from this class support the potential of H3 receptor antagonists for the treatment of cognitive dysfunction.

A new class of potent non-imidazole H3 antagonists: 2-Aminoethylbenzofurans

2-Aminoethylbenzofurans constitute a new class of H3 antagonists that are more rotationally constrained than most previously reported H3 antagonists. They retain high potency at human and rat receptors, with efficient CNS penetration observed in 35. The SAR of the basic amine moiety was compared in three different series of analogues. The greatest potency was found in analogues bearing a 2-methylpyrrolidine, a 2,5-dimethylpyrrolidine, or a 2,6-dimethylpiperidine.