2033-76-3

Usage

Uses

Used in Chemical Synthesis:
1-(2-BROMOETHOXY)-4-CHLOROBENZENE is used as a synthetic intermediate for [application reason] in the chemical industry. Its unique structure allows it to be a valuable building block in the creation of various complex organic molecules, contributing to the development of new compounds with potential applications in different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(2-BROMOETHOXY)-4-CHLOROBENZENE is used as a key component in the development of new drugs for [application reason]. Its specific functional groups and structural features make it an attractive candidate for the design and synthesis of novel therapeutic agents.
Used in Agrochemical Industry:
1-(2-BROMOETHOXY)-4-CHLOROBENZENE is also utilized as a starting material in the agrochemical industry for [application reason]. Its properties enable the synthesis of various agrochemicals, such as pesticides and herbicides, which are essential for maintaining agricultural productivity and crop protection.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 1-(2-BROMOETHOXY)-4-CHLOROBENZENE is used as a precursor for the synthesis of various dyes and pigments for [application reason]. Its unique chemical structure allows for the creation of a wide range of colors and properties, making it a valuable asset in the development of new dyes and pigments for various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C8H8BrClO/c9-5-6-11-8-3-1-7(10)2-4-8/h1-4H,5-6H2

Upstream product

• 106-48-9 4-chloro-phenol 
• 106-93-4 ethylene dibromide 
• 1121-74-0 potassium 4-chlorophenoxide 
• 2446-83-5 diisopropyl (E)-azodicarboxylate 
• 540-51-2 2-bromoethanol 

Downstream Products

• 109185-16-2 ethyl-[2-(4-chloro-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 29811-99-2 [2-(4-chloro-phenoxy)-ethyl]-heptyl-dimethyl-ammonium; bromide 
• 29812-00-8 [2-(4-chloro-phenoxy)-ethyl]-dimethyl-octyl-ammonium; bromide 
• 15687-13-5 [2-(4-chloro-phenoxy)-ethyl]-dodecyl-dimethyl-ammonium; bromide 
• 16723-94-7 1,2-Bis-(4-chlor-phenoxy)-aethan 
• 109726-05-8 [2-(4-chloro-phenoxy)-ethyl]-dimethyl-propyl-ammonium; bromide 
• 132493-67-5 butyl-[2-(4-chloro-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 132886-36-3 [2-(4-chloro-phenoxy)-ethyl]-dimethyl-pentyl-ammonium; bromide 
• 29811-98-1 [2-(4-chloro-phenoxy)-ethyl]-hexyl-dimethyl-ammonium; bromide 
• 26666-43-3 [2-(4-chloro-phenoxy)-ethyl]-decyl-dimethyl-ammonium; bromide 
• 29812-02-0 [2-(4-chloro-phenoxy)-ethyl]-dimethyl-tetradecyl-ammonium; bromide 
• 29812-03-1 [2-(4-chloro-phenoxy)-ethyl]-hexadecyl-dimethyl-ammonium; bromide 
• 121991-15-9 [2-(4-chloro-phenoxy)-ethyl]-dimethyl-octadecyl-ammonium; bromide 
• 1074-56-2 p-chlorophenyl vinyl ether 

Relevant academic research and scientific papers

Solubility of 1-(3-bromopropoxy)-4-chlorobenzene in aqueous ethanol mixtures from (273.15 to 303.15) K

1-(3-Bromopropoxy)-4-chlorobenzene is an important intermediate for the manufacture of omoconazole nitrate. The solubilities of 1-(3-bromopropoxy)-4- chlorobenzene in aqueous ethanol solutions were measured within the temperature range of (273.15-303.15) K using a laser monitoring system. For the temperature range investigated, the solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in the aqueous ethanol mixtures increase with increasing temperature. The solubility data were regressed by the Buchowski-Ksiazaczak λh and the modified Apelblat models. The modified Apelblat equation and the Buchowski-Ksiazaczak λh equation provided accurate mathematical representations of the experimental results. The calculated solubilities showed good agreement with the experimental data. The root-mean-square deviations of the modified Apelblat model were lower than those of the Buchowski-Ksiazaczak λh model. This study provided valuable data for the purification of 1-(3-bromopropoxy)-4-chlorobenzene by crystallization.

Carboxylic acids and skeletal muscle chloride channel conductance: Effects on the biological activity induced by the introduction of an aryloxyalkyl group α to the carboxylic function of 4-chloro-phenoxyacetic acid

2-(4-Chloro-phenoxy)propanoic and 2-(4-chloro-phenoxy)butanoic acids are compounds known to block chloride membrane conductance in rat striated muscle by interaction with a specific receptor. In the present study, a series of chiral analogues has been prepared and tested to evaluate the influence of a second aryloxy moiety introduced in the side-chain at a variable distance from the stereogenic centre. The results show that this chemical modification is detrimental for biological activity which, however, is increased by lengthening the alkyl chain up to three methylenic groups, then decreases to remain constant in the next analogues of the series. A possible explanation for this is proposed on the basis of steric effects and/or different approach of the molecules to the receptor.

Anchimerically Activated ProTides as Inhibitors of Cap-Dependent Translation and Inducers of Chemosensitization in Mantle Cell Lymphoma

The cellular delivery of nucleotides through various pronucleotide strategies has expanded the utility of nucleosides as a therapeutic class. Although highly successful, the highly popular ProTide system relies on a four-step enzymatic and chemical process to liberate the corresponding monophosphate. To broaden the scope and reduce the number of steps required for monophosphate release, we have developed a strategy that depends on initial chemical activation by a sulfur atom of a methylthioalkyl protecting group, followed by enzymatic hydrolysis of the resulting phosphoramidate monoester. We have employed this ProTide strategy for intracellular delivery of a nucleotide antagonist of eIF4E in mantle cell lymphoma (MCL) cells. Furthermore, we demonstrated that chemical inhibition of cap-dependent translation results in suppression of c-Myc expression, increased p27 expression, and enhanced chemosensitization to doxorubicin, dexamethasone, and ibrutinib. In addition, the new ProTide strategy was shown to enhance oral bioavailability of the corresponding monoester phosphoramidate.

Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives

In view of obtaining some potential antibacterial compounds, we have described synthesis of some chloroaryloxyalkyl imidazole and benzimidazole derivatives. The relevant step in the synthetic sequence was the initial condensation of 4-chloro or 2,4-dichlorophenol with 1, n-dibromoalkanes (n = 2, 4, 5) to provide compounds 3a-f in sufficient yields. The subsequent condensation of 3a-f with some imidazole derivatives and benzimidazole afforded products 4a-l and 5a-e in good yields. Some of compounds 4a-l as well as 5a-e were tested in vitro against Salmonella typhi O-901 and Staphylococcus aureus A 15091. Compounds 4a and 4c showed considerable bactericidal activities against tested bacteria. Compound 4b showed significant activity against S. aureus A 15091 but was inactive against S. typhi O-901. Other compounds showed intermediate activities against S. aureus A 15091 but most of them were inactive against S. typhi O-901. Semiempirical AM1 calculations showed that negative electrostatic potentials around oxygen of the phenoxy and nitrogen of the imidazole moieties have direct effect on the antibacterial activity towards S. aureus A 15091. In QSAR analysis, different electronic, topologic, functional groups and physicochemical descriptors were calculated for each molecule and a three parametric equation was found between the log MIC and HOMO energy, hydration energy and number of primary carbon atoms of the molecules.

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.].

Dofetilide-d3 drug and preparation method thereof

The invention discloses a dofetilide-d3 drug and a preparation method thereof. The preparation method comprises the following steps: reacting p-chlorophenol with 1, 2-dibromoethane in ethanol at the temperature of 100 DEG C in the presence of sodium hydroxide serving as alkali to obtain a compound III; reacting the compound III with 4-chlorophenylethylamine in a second solvent at 80 DEG C in the presence of alkali to obtain a compound I; reacting the compound I with deuterium sources under the catalysis of a light source and a photocatalyst to obtain a compound II, wherein the deuterium sources comprise deuterium water and d4-deuterated methanol; and reacting the compound II with methanesulfonamide under the catalysis of a palladium catalyst to obtain the docetaxel-d3 drug. According to the preparation method, more environment-friendly and cheap deuterium water and d4-deuterated methanol are used as deuterium sources, the d4-deuterated methanol is used as a deuterium methyl source, andselective N-deuterium methylation reaction on a prodrug amine compound is realized at normal temperature and normal pressure under the action of photocatalysis of a photocatalyst, so that the docetaxel-d3 drug is prepared.

Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist

To identify novel D3 dopamine receptor (D3R) agonists, we conducted a high-throughput screen using a β-arrestin recruitment assay. Counterscreening of the hit compounds provided an assessment of their selectivity, efficacy, and potency. The most promising scaffold was optimized through medicinal chemistry resulting in enhanced potency and selectivity. The optimized compound, ML417 (20), potently promotes D3R-mediated β-arrestin translocation, G protein activation, and ERK1/2 phosphorylation (pERK) while lacking activity at other dopamine receptors. Screening of ML417 against multiple G protein-coupled receptors revealed exceptional global selectivity. Molecular modeling suggests that ML417 interacts with the D3R in a unique manner, possibly explaining its remarkable selectivity. ML417 was also found to protect against neurodegeneration of dopaminergic neurons derived from iPSCs. Together with promising pharmacokinetics and toxicology profiles, these results suggest that ML417 is a novel and uniquely selective D3R agonist that may serve as both a research tool and a therapeutic lead for the treatment of neuropsychiatric disorders.

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.

Synthesis of Novel Aryloxyethylamine Derivatives and Evaluation of Their in Vitro and in Vivo Neuroprotective Activities

A series of aryloxyethylamine derivatives were designed, synthesized and evaluated for their biological activity. Their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR and HR-ESI-MS. The preliminary screening of neuroprotection of compounds in vitro was detected by MTT, and the anti-ischemic activity in vivo was tested using bilateral common carotid artery occlusion in mice. Most of these compounds showed potential neuroprotective effects against the glutamate-induced cell death in differentiated rat pheochromocytoma cells (PC12 cells), especially for (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone, (4-bromophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, (4-chlorophenyl)(1-{2-[(naphthalen-2-yl)oxy]ethyl}piperidin-4-yl)methanone, (4-chlorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone and {1-[2-(4-bromophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, which exhibited potent protection of PC12 cells at three doses (0.1, 1.0, 10 μM). Compounds (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, (4-fluorophenyl){1-[2-(naphthalen-2-yloxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed the significant prolongation of the survival time of mice subjected to acute cerebral ischemia and decreased the mortality rate at all five doses tested (200, 100, 50, 25, 12.5 mg/kg) and had significant neuroprotective activity. In addition, (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed outstanding neuroprotection in vitro and in vivo. These compounds can be used as a promising neuroprotective agents for future development of new anti-ischemic stroke agents. Basic structure–activity relationships are also presented.

1-aryloxy ethyl piperidine-4-yl benzophenone derivative as well as preparation method and application thereof

The invention discloses a 1-aryloxy ethyl piperidine-4-yl benzophenone derivative as well as a preparation method and application thereof. The compound is a free alkali or salt with a compound of a formula (I) shown in the specification; the salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetate, tartrate, lactate or mesylate; in the formula, R1 independently represents H, halogen,alkyl, halogen-substituted alkyl, nitryl, amino, nitrile, hydroxyl, alkoxy, aryl alkoxy, heterocyclic alkoxy, aryl, substituted heterocyclic ring or substituted aryl; and R2 is independently selectedfrom H, halogen, alkyl, halogen substituted alkyl, nitryl, amino, nitrile, hydroxyl, alkoxy, aryl alkoxy, heterocyclic alkoxy, aryl, substituted heterocyclic ring or substituted aryl. The 1-aryloxy ethyl piperidine-4-yl benzophenone derivative is applied to preparation of medicines for treating cerebral arterial thrombosis.