18800-34-5

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C9H11BrO/c1-8-2-4-9(5-3-8)11-7-6-10/h2-5H,6-7H2,1H3

Upstream product

• 106-44-5 p-cresol 
• 106-93-4 ethylene dibromide 
• 1192-96-7 potassium p-cresolate 
• 15149-10-7 2-(4-methylphenoxy)ethanol 

Downstream Products

• 97375-48-9 1-(2-methoxyethoxy)-4-methylbenzene 
• 15149-11-8 1,1'-[ethane-1,2-diylbis(oxy)]bis(4-methylbenzene) 
• 26583-58-4 β-(2-methylphenoxy)ethylamine 
• 150058-40-5 N-(2-p-tolyloxy-ethyl)-phthalimide 
• 860579-11-9 2-(2-p-tolyloxy-ethyl)-acetoacetic acid ethyl ester 
• 1005-62-5 4-tolyl vinyl ether 
• 136263-92-8 1-ethoxy-2-p-tolyloxy-ethane 
• 51616-09-2 4-(β-bromoethoxy)benzoic acid 
• 806600-19-1 2-[bis-(2-p-tolyloxy-ethyl)-amino]-ethanol 
• 51344-14-0 N,N-dimethyl-2-<4-methylphenoxy>-ethylamine 
• 6974-08-9 trimethyl-(2-p-tolyloxy-ethyl)-ammonium; bromide 
• 98155-61-4 1-phenoxy-2-p-tolyloxy-ethane 
• 67746-93-4 Propyl-(2-p-tolyloxy-ethyl)-amine 
• 53995-39-4 2-(2-hydroxy-phenyl)-4-(2-p-tolyloxy-ethyl)-4H-[1,3,4]oxadiazin-5-one 

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.].

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.

Benzo[d]isothiazole-3-(2H)-one derivative, preparation method and application thereof

The invention relates to a benzo[d]isothiazole-3-(2H)-one derivative, a preparation method and application of the benzo[d]isothiazole-3-(2H)-one derivative. The compound is a free alkali or salt of acompound with a structure shown in a general formula (I). The salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetate, tartrate, lactate or mesylate; R1 independently represents "-CH2-CO-" or "-CH2-CH2-"; R2 independently represents "-CH2-CH2-O-" or "-CO-CH=CH-"; R3 independently represents hydrogen, halogens, a hydrocarbon group, a halogen-substituted hydrocarbon group, a nitro group, an amino group, a nitrile group, a hydroxyl group, an alkoxy group, an aryloxy group, a heterocycloalkoxy group, an aryl group, a substituted heterocyclic ring or a substituted aryl group. The invention also provides an application of the benzo[d]isothiazole-3-(2H)-one derivative in preparation of ischemic stroke treatment medicines.

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.

The steric hindrance controlled [2]pseudorotaxanes constructed by V-type stilbene dyes?CB[7]

In this paper, five V-type stilbene dyes (VD, 1a-1e) that had unchanged dimethylamino phenylethenyl (DMPE) arm as inclusive location with CB[7] and another arm with different steric hindrance aryloxyethyl (AE) group were designed and synthesized. Their inclusive characteristics and stability to CB[7] were studied. Fluorescence spectroscopy and 1H NMR method were used respectively to study the inclusive characteristics of 1a?CB[7], 1b?CB[7], 1c?CB [7], 1d?CB[7] and 1e?CB[7]. Fitting curves results of fluorescent titration indicated that 1:1 complexes between CB[7] and VD were constructed, and their inclusive constants were calculated respectively. The order of inclusive constants K1a?CB[7]>?K1b?CB[7]>?K1c?CB[7] >?K1d?CB[7] was consistent with the magnitude of the steric hindrance, however, 1e did not include with CB[7]. Therefore, a series of steric hindrance controlled [2]pseudorotaxanes were constructed.

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.

Design and synthesis of guanylthiourea derivatives as potential inhibitors of Plasmodium falciparum dihydrofolate reductase enzyme

A new class of compounds based on S-benzylated guanylthiourea has been designed as potential PfDHFR inhibitors using computer aided methods (molecular electrostatic potential, molecular docking). Several compounds in this class have been synthesized start

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, biological activity evaluation and molecular modeling study on the new isoconessimine derivatives as acetylcholinesterase inhibitors

New isoconessimine derivatives were synthesized from conessine (1) and evaluated as acetylcholinesterase (AChE) inhibitors. The derivatives were prepared via two reaction steps, N-demethylation and nucleophilic substitution. All of the synthesized derivatives exhibited more potential anti- acetylcholinesterase activities than conessine (1) (IC50=16 μmol·L-1) and isoconessimine (2) (IC50>300 μmol·L-1). Compound 7b (3β-[methyl-[2-(4-nitrophenoxy) ethyl]amino]con-5-enine) showed the most potent inhibitory activity with an IC50 of 110 nmol/L which is close to that of reference compound huperzine A (IC50=70 nmol/L). The mode of AChE inhibition by 7b was reversible and non-competitive. In addition, molecular modeling was performed to explore the binding mode of inhibitor 7b at the active site of AChE and the results showed that 7b could be docked into the acetylcholinesterase active site and compound 7b had hydrophobic interactions with Trp279 and Leu282. A series of 3-N-aryloxyethyl substitutional isoconessimine derivatives were synthesized and evaluated as acetylcholinesterase (AChE) inhibitors. All of the synthesized derivatives exhibited potential anti-acetylcholinesterase activities with IC50 values at micromolar to sub-micromolar range. 7b showed the most potent inhibitory activity with an IC50of 110 nmol/L. The molecular docking results showed that 7b can be well docked into the active site of acetylcholinesterase. Copyright

Synthesis and anticonvulsant evaluation of some N-substituted phthalimides

Two series of phthalimides - one possessing an N-phenoxyalkyl moiety substituted at position 3 or 4 of the phenyl ring (1-9) and the other of N-alkenyl or alkinyl phthalimides (10-18) - were synthesized, evaluated for anticonvulsant activity and had their in silico lipophilicity estimated using computer programs. The anticonvulsant activity of phthalimides containing an unsaturated substituent at the phthalimide nitrogen was superior to that of the N-phenoxyalkyl phthalimides. Alkinyl derivative 10 emerged as the most active (in MES and ScMet tests) of all the compounds tested. A correlation between anticonvulsant activity and in silico estimated lipophilicity was not observed.