332-48-9

Usage

Chemical Properties

clear colorless to brownish liquid after melting

InChI:InChI=1/C8H8BrFO/c1-6(9)11-8-4-2-7(10)3-5-8/h2-6H,1H3

Upstream product

• 371-41-5 4-Fluorophenol 
• 106-93-4 ethylene dibromide 

Downstream Products

• 6096-72-6 {[2-(4-Fluoro-phenoxy)-ethyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester 
• 79808-04-1 C₁₄H₁₂FNO₄ 
• 103197-02-0 N-benzoyl-2-(2-bromoethoxy)-5-fluorophenylglycine 
• 103197-05-3 N-acetyl-2-(2-bromoethoxy)-5-fluorophenylglycine 
• 145276-55-7 6-<4-<2-(4-fluorophenoxy)ethyl>-1-piperazinyl>-3(2H)-pyridazinone 
• 114997-84-1 [2-(4-Fluoro-phenoxy)-ethyl]-hydrazine 
• 52161-83-8 2-Acetylamino-2-[2-(4-fluoro-phenoxy)-ethyl]-malonic acid diethyl ester 
• 52161-84-9 O-4-fluorophenylhomoserine 
• 263409-81-0 2-(4-fluorophenoxy)ethan-1-amine hydrochloride 
• 947695-05-8 4-[2-(4-fluorophenoxy)ethyl]piperazine-1-carboxylic acid tert-butyl ester 
• 364339-37-7 C₁₅H₁₄FN₃O 
• 725703-13-9 2-(2-(4-fluorophenoxy)ethyl)isoindoline-1,3-dione 
• 121773-17-9 2-Benzoylamino-4-(4-fluoro-phenoxy)-butyric acid methyl ester 
• 121773-22-6 2-Benzoylamino-4-(4-fluoro-phenoxy)-2-methoxy-butyric acid methyl ester 

Relevant academic research and scientific papers

Quinolinesulfonamides of aryloxy-/arylthio-ethyl piperidines: Influence of an arylether fragment on 5-HT1A/5-HT7 receptor selectivity

The solid-phase synthesis of a new series of 19 biomimetics of long-chain arylpiperazines, namely flexible quinoline sulfonamides of aryl(heteroaryl)oxy-/ heteroarylthio-ethyl 4-aminomethylpiperidines, is reported. Various structural modifications applied followed by biological evaluation for 5-HT1A, 5-HT6, and 5-HT7 receptors gave further support of a possible replacement of arylpiperazine with aryloxy-/arylthio-ethyl derivatives of alicyclic amines and control of receptor selectivity upon diversification in the aryl(heteroaryl)oxy-/heteroarylthio-ethyl fragment. The solid-phase synthesis of a new series of 19 biomimetics of long-chain arylpiperazines is reported. Biological evaluation for 5-HT1A, 5-HT6, and 5-HT7 receptors supported the possible replacement of the arylpiperazine with aryloxy-/arylthio-ethyl derivatives of alicyclic amines and the control of receptor selectivity upon diversification in the aryl(heteroaryl)oxy-/heteroarylthio-ethyl fragment.

Synthesis and biological evaluation of sphingosine kinase 2 inhibitors with anti-inflammatory activity

The synthesis of inhibitors of SphK2 with novel structural scaffolds is reported. These compounds were designed from a molecular modeling study, in which the molecular interactions stabilizing the different complexes were taken into account. Particularly

Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids

Abstract: Antimicrobial resistance has become a significant threat to global public health, thus precipitating an exigent need for new drugs with improved therapeutic efficacy. In this regard, molecular hybridization is deemed as a viable strategy to afford multi-target-based drug candidates. Herein, we report a library of quinoline—1H-1,2,3-triazole molecular hybrids synthesized via copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39?μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C. albicans and C. neoformans at an MIC80 value of 37.69 and 2.36?μM, respectively, superior to fluconazole. In vitro toxicity profiling revealed non-hemolytic activity against human red blood cells (hRBC) but partial cytotoxicity to human embryonic kidney cells (HEK293). Additionally, in silico studies predicted excellent drug-like properties and the importance of triazole ring in stabilizing the complexation with target proteins. Overall, these results present compound 16 as a promising scaffold on which other molecules can be modeled to deliver new antimicrobial agents with improved potency. Graphic abstract: [Figure not available: see fulltext.].

Discovery of Novel pERK1/2- or β-Arrestin-Preferring 5-HT1AReceptor-Biased Agonists: Diversified Therapeutic-like versus Side Effect Profile

Novel 1-(1-benzoylpiperidin-4-yl)methanamine derivatives with high affinity and selectivity for serotonin 5-HT1A receptors were obtained and tested in four functional assays: ERK1/2 phosphorylation, adenylyl cyclase inhibition, calcium mobilization, and β-arrestin recruitment. Compounds 44 and 56 (2-methylaminophenoxyethyl and 2-(1H-indol-4-yloxy)ethyl derivatives, respectively) were selected as biased agonists with highly differential "signaling fingerprints"that translated into distinct in vivo profiles. In vitro, 44 showed biased agonism for ERK1/2 phosphorylation and, in vivo, it preferentially exerted an antidepressant-like effect in the Porsolt forced swimming test in rats. In contrast, compound 56 exhibited a first-in-class profile: it preferentially and potently activated β-arrestin recruitment in vitro and potently elicited lower lip retraction in vivo, a component of "serotonergic syndrome". Both compounds showed promising developability properties. The presented 5-HT1A receptor-biased agonists, preferentially targeting various signaling pathways, have the potential to become drug candidates for distinct central nervous system pathologies and possessing accentuated therapeutic activity and reduced side effects.

DOPAMINE D2 RECEPTOR LIGANDS

The present invention relates to novel dopamine D2 receptor ligands. The invention further relates to functionally-biased dopamine D2 receptor ligands and the use of these compounds for treating or preventing central nervous system and systemic disorders associated with dysregulation of dopaminergic activity. The present invention relates to novel compounds that modulate dopamine D2 receptors. In particular, compounds of the present invention show functional selectivity at the dopamine D2 receptors and exhibit selectivity downstream of the D2 receptors, on the 0- arrestin pathway and/or on the cAMP pathway.

DOPAMINE D2 RECEPTOR LIGANDS

The present invention relates to novel dopamine D2 receptor ligands. The invention further relates to functionally-biased dopamine D2 receptor ligands and the use of these compounds for treating or preventing central nervous system and systemic disorders associated with dysregulation of dopaminergic activity.

Discovery of 1-aryloxyethyl piperazine derivatives as Kv1.5 potassium channel inhibitors (part I)

Kv1.5 potassium channel is an efficacious and safe therapeutic target for the treatment of atrial fibrillation (AF), the most common arrhythmia that threatens human. Herein, by modifying the hit compound 7k from an in-house database, 48 derivatives were synthesized for the assay of their Kv1.5 inhibitory effects by whole cell patch clamp technique. Six compounds which showed better potency than the positive compound dronedarone were selected for the next evaluation of their drug-like properties. Compound 8 exhibited balanced solubility and permeability. It also showed acceptable pharmacodynamics profile with very low acute toxicity. Taking all these data into account, compound 8 can serve as a promising lead for the development of novel therapeutic agent for the treatment of AF.

Synthesis of new (arylcarbonyloxy)aminopropanol derivatives and the determination of their physico-chemical properties

Eight hydrochlorides of 3-{2-[(2/4-fluorophenoxy)-ethylamino]}-2- hydroxypropyl-4-alkoxybenzoates and four hydrochlorides of 3-tert-butylamino-2- hydroxypropyl-4-butoxybenzoates were prepared as potential antagonists of the β1-adrenergic receptor (beta-blockers). A multistep synthesis of these compounds is described as well as their detailed analytical characterization. The pharmacokinetic properties of these weak base compounds are significantly influenced by their acid-base dissociation constant, pK a. The knowledge of this value is crucial for new drug development. This paper is aimed at developing a methodology that utilizes pH-dependent 1H NMR spectroscopy for its routine analysis. The selected predicted physico-chemical parameters of the new (arylcarbonyloxy)aminopropanols (i.e., aryloxyaminopropanol derivatives) were compared with the model drugs esmolol and flestolol. [Figure not available: see fulltext.]

CYCLOHEXYLAMINE DERIVATIVE CONTAINING PHENYL GROUP, AND THERAPEUTIC AGENT FOR DISEASES ACCOMPANIED BY CENTRAL NERVOUS SYSTEM DISORDERS

Disclosed is a novel cyclohexylamine derivative containing a phenyl group, which is useful as a novel sigma receptor ligand. Also disclosed is a therapeutic agent for diseases accompanied by a central nervous system disorder, which comprises the compound as an active ingredient. The therapeutic agent comprises a compound represented by general formula [1] or a pharmacologically acceptable salt thereof as an active ingredient: wherein X and Y independently represent a hydrogen atom, a halogen atom, a trihalomethyl group, a dihalomethyl group, a monohalomethyl group, a methoxy group, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms; R1, R2, R3 and R4 independently represent a hydrogen atom, a hydroxyl group, an alkoxyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms; R5 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkylene group which has 2 to 4 carbon atoms and can bind to a carbon atom other than carbon atoms that bind to a nitrogen atom on the cyclohexyl ring to form a ring; n represents an integer of to 5; and represents a sulfur atom, a carbon atom, or an oxygen atom.

Pharmacophore-based discovery, synthesis, and biological evaluation of 4-phenyl-1-arylalkyl piperidines as dopamine transporter inhibitors

Pharmacophore-based discovery, synthesis, and structure-activity relationship (SAR) of a series of 4-phenyl-1-arylalkyl piperidines are disclosed. These compounds have been evaluated for their ability to inhibit reuptake of dopamine (DA) into striatal nerve endings (synaptosomes). The lead compound 5 and the most potent analogue 43 were found to have significant functional antagonism.