460746-48-9

Usage

Uses

Used in Pharmaceutical Industry:
4-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]-benzonitrile is used as a potential drug candidate for the development of medications targeting various conditions and diseases. Its unique chemical structure, which combines benzofuran and benzonitrile moieties with a hydroxyethyl group, may contribute to its therapeutic effects and make it a valuable asset in the discovery and design of new pharmaceutical agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]-benzonitrile serves as a subject of study for understanding its properties, interactions with biological targets, and potential mechanisms of action. Researchers are interested in exploring its pharmacological profile, including its binding affinity, selectivity, and efficacy in treating specific conditions, as well as its safety and toxicity profiles.
Used in Drug Discovery and Design:
4-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]-benzonitrile is utilized in drug discovery and design processes to identify novel therapeutic agents with improved efficacy, selectivity, and safety profiles. Its unique structural features may offer new opportunities for the development of drugs with innovative mechanisms of action, addressing unmet medical needs and providing new treatment options for patients.
Used in Chemical Synthesis and Modification:
In chemical synthesis, 4-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]-benzonitrile can be employed as a starting material or intermediate for the synthesis of more complex molecules with potential pharmaceutical applications. Its chemical properties, such as reactivity and stability, can be further explored and modified to create new derivatives with enhanced or novel therapeutic properties.

InChI:InChI=1/C17H13NO2/c18-11-12-1-3-13(4-2-12)14-5-6-17-15(9-14)10-16(20-17)7-8-19/h1-6,9-10,19H,7-8H2

Upstream product

• 927-74-2 3-Butyn-1-ol 
• 460746-47-8 4'-hydroxy-3'-iodo[1,1'-biphenyl]-4-carbonitrile 
• 126747-14-6 4-cyanophenylboronic acid 
• 460748-15-6 2-(5-bromo-1-benzofuran-2-yl)ethanol 
• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 

Downstream Products

• 460746-49-0 2-[5-(4-cyanophenyl)-1-benzofuran-2-yl]ethyl methanesulfonate 
• 460746-46-7 4-{2-[2-(2R-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}benzonitrile 
• 670342-24-2 toluene-4-sulfonic acid 2-[5-(4-cyano-phenyl)benzofuran-2-yl]ethyl ester 
• 460748-71-4 4-{2-[2-((R)-2-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}benzonitrile L-tartrate 

Relevant academic research and scientific papers

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 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).

PROCESS FOR PREPARING AMINE-SUBSTITUTED BENZOFURANS

The present invention relates to processes for preparing amine substituted benzofurans, and more particularly 4-(2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile, and salts thereof. Compounds prepared by the processes of the invention have demonstrated activity as histamine-3 receptor ligands.

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.

Histamine-3 receptor ligands for diabetes conditions

The invention relates to a method of treating a diabetic condition by administering a therapeutically effective amount of a histamine-3 receptor antagonist, including benzofuran and benzopyran derivatives of formula (I), aminoalkoxybiphenylcarboxamide compounds of formula (III), and aminoetherbiphenyl compounds of formula (IV) as described herein.

Histamine-3 receptor ligands for diabetic conditions

The invention relates to a method of treating a diabetic condition by administering a therapeutically effective amount of a histamine-3 receptor antagonist, including benzofuran and benzopyran derivatives of formula (I), aminoalkoxybiphenylcarboxamide compounds of formula (III), and aminoetherbiphenyl compounds of formula (IV) as described herein.

Novel amines as histamine-3 receptor ligands and their therapeutic applications

Compounds of formula (I) or a pharmaceutically acceptable salts or prodrug thereof which are useful for the modulation of the histamine-3 receptors in mammals and which are useful for the treatment of disorders ameliorated by histamine-3 receptor ligands.

Novel amines as histamine-3 receptor ligands and their therapeutic applications

Compounds of formula (I) or a pharmaceutically acceptable salts or prodrug thereof which are useful for the modulation of the histamine-3 receptors in mammals and which are useful for the treatment of disorders ameliorated by histamine-3 receptor ligands.