18800-26-5

Usage

Chemical Properties

Clear slightly yellow liquid

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

Upstream product

• 95-57-8 2-monochlorophenol 
• 106-93-4 ethylene dibromide 

Downstream Products

• 111354-75-7 ethyl-[2-(2-chloro-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 29811-93-6 [2-(2-chloro-phenoxy)-ethyl]-heptyl-dimethyl-ammonium; bromide 
• 29811-94-7 [2-(2-chloro-phenoxy)-ethyl]-dimethyl-octyl-ammonium; bromide 
• 29811-96-9 [2-(2-chloro-phenoxy)-ethyl]-dodecyl-dimethyl-ammonium; bromide 
• 109725-92-0 [2-(2-chloro-phenoxy)-ethyl]-dimethyl-propyl-ammonium; bromide 
• 132493-60-8 butyl-[2-(2-chloro-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 132886-37-4 [2-(2-chloro-phenoxy)-ethyl]-dimethyl-pentyl-ammonium; bromide 
• 132753-65-2 [2-(2-chloro-phenoxy)-ethyl]-hexyl-dimethyl-ammonium; bromide 
• 29811-95-8 [2-(2-chloro-phenoxy)-ethyl]-decyl-dimethyl-ammonium; bromide 
• 30035-86-0 [2-(2-chloro-phenoxy)-ethyl]-dimethyl-tetradecyl-ammonium; bromide 
• 29811-97-0 [2-(2-chloro-phenoxy)-ethyl]-hexadecyl-dimethyl-ammonium; bromide 
• 496-16-2 2.3-dihydrobenzofuran 
• 38380-93-7 (2-chloro-phenyl)-vinyl ether 
• 70289-29-1 [2-(2-chloro-phenoxy)-ethyl]-methyl-amine 

Relevant academic research and scientific papers

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.].

Amino Acid Hot Spots of Halogen Bonding: A Combined Theoretical and Experimental Case Study of the 5-HT7 Receptor

A computational approach combining a structure-activity relationship library of halogenated and the corresponding unsubstituted ligands (called XSAR) with QM-based molecular docking and binding free energy calculations was used to search for amino acids frequently targeted by halogen bonding (hot spots) in a 5-HT7R as a case study. The procedure identified two sets of hot spots, extracellular (D2.65, T2.64, and E7.35) and transmembrane (C3.36, T5.39, and S5.42), which were further verified by a synthesized library of halogenated arylsulfonamide derivatives of (aryloxy)ethylpiperidines. It was found that a halogen bond formed between T5.39 and a bromine atom at 3-position of the aryloxy fragment caused the most remarkable, 35-fold increase in binding affinity for 5-HT7R when compared to the nonhalogenated analog. The proposed paradigm of halogen bonding hot spots was additionally verified on D4 dopamine receptor showing that it can be used in rational drug design/optimization for any protein target.

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.

Renin inhibitors

The invention relates to compounds having the formula: wherein the variables are as defined herein. The invention further relates to methods of making and using these compounds, and pharmaceutical compositions, kits and articles of manufacture comprise th

A practical synthesis of sarpogrelate hydrochloride and in vitro platelet aggregation inhibitory activities of its analogues

A convenient approach for the preparation of sarpogrelate hydrochloride was developed. Two series of sarpogrelate hydrochloride analogues were designed and synthesized in order to improve their platelet aggregation inhibitory activities, biological tests suggested that these compounds have platelet aggregation inhibitory activities to some extent.

Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α1d Adrenergic Receptor

In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the α1d adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three α1-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the α1d-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BMY 7378 and 69 into the putative binding sites of the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2 (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for α1d adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.

Novel synthetic strategy of N-arylated heterocycles via sequential palladium-catalyzed intra- and inter-arylamination reactions

The use of an in situ generated Pd(0) catalyst associated to N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and t-BuONa as the base for sequential intra- followed by intermolecular aryl animation is described. The method has been applied to the synthesis of N-arylated five-, six- and seven-membered nitrogen heterocycles.

A simple modification of the known preparation procedure of 2-Phenoxyethyl bromides providing high yields

A modification of preparation method was developed for synthesis of a number of 1-bromo-2-phenoxyethanes from 1,2-dibromoethanes and sodium phenolates in two-phase water-organic system with or without addition of triethylbenzylammonium chloride as phase-transfer catalyst. Addition of NaOH in two portions for transforming phenols into phenolates ensured high yields (60-80%) of phenoxylation products.