4698-96-8

Usage

Uses

Used in Organic Synthesis:
2-((1,1’-biphenyl-4-yloxy)methyl)-oxiran is used as a building block in organic synthesis for its ability to form a variety of chemical products. Its reactive epoxide group facilitates the creation of polymers, resins, and other materials, making it a valuable component in the development of new compounds with diverse applications.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 2-((1,1’-biphenyl-4-yloxy)methyl)-oxiran is used as a potential candidate for drug development due to its unique structure and properties. Its reactivity allows for the formation of new compounds that could have therapeutic effects, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Applications:
Similarly, in agrochemicals, 2-((1,1’-biphenyl-4-yloxy)methyl)-oxiran is utilized for its potential to create new compounds with pesticidal or herbicidal properties. Its incorporation into agrochemical products can lead to the development of more effective and targeted solutions for crop protection.
Used in Polymer and Resin Production:
2-((1,1’-biphenyl-4-yloxy)methyl)-oxiran is also used in the production of polymers and resins, where its reactive nature is leveraged to create materials with specific properties. These materials can be tailored for use in various industries, including coatings, adhesives, and composites, enhancing their performance and versatility.

InChI:InChI=1/C15H14O2/c1-2-4-12(5-3-1)13-6-8-14(9-7-13)16-10-15-11-17-15/h1-9,15H,10-11H2/t15-/m0/s1

Upstream product

• 92-69-3 4-Phenylphenol 
• 106-89-8 epichlorohydrin 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 

Downstream Products

• 5741-13-9 1-([1,1'-biphenyl]-4-yloxy)-3-(isopropylamino)propan-2-ol 
• 391901-99-8 (2 S)-1-[(4-aminophenethyl)amino]-3-([1,1'-biphenyl]-4-yloxy)-2-propanol 
• 81015-20-5 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-(4-biphenyloxy)-2-propanol 
• 797814-46-1 3-(3'-(4''-phenylphenoxy)-2'-hydroxypropyl)-5,5-dimethylimidazolidine-2,4-dione 
• 127038-44-2 4-(3-(biphenyl-4-yloxy)-2-hydroxypropylthio)phenol 
• 5305-17-9 C₁₉H₂₃NO₂ 
• 5262-74-8 1-biphenyl-4-yloxy-3-morpholin-4-yl-propan-2-ol 
• 61485-61-8 VUF14176 
• 1399845-85-2 C₂₃H₂₄FNO₂ 
• 5305-36-2 1-(Biphenyl-4-yloxy)-3-diethylamino-propan-2-ol 
• 1399845-88-5 C₂₂H₂₂FNO₂ 
• 1399845-86-3 C₂₂H₂₁F₂NO₂ 
• 1399845-84-1 C₂₂H₂₃NO₂ 

Relevant academic research and scientific papers

Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents

Malignant melanoma (MM) presents as the highest morbidity and mortality type in skin cancer. Herein, inspired by the previously reported anti-melanoma effect of propranolol, a widely applied β adrenergic receptor antagonist as cardiovascular drug, we set out to exploit its potential as anti-melanoma therapy based on the drug repurposing strategy. Structural optimization of propranolol yielded 5m, which exhibits dramatically improved potency on human melanoma cell growth (1.98–3.70 μM), compared to propranolol (59.5–75.8 μM). Further investigation demonstrated that 5m could inhibit colony formation of melanoma cell line (completely abolished at 2 μM for 5m, partially inhibited at 50 μM for propranolol), induce cell apoptosis and cell cycle arrest in the G2/M phase (both observed at 1 μM). Preliminary mechanism study indicated that 5m could disrupt the cellular microtubule network, which suggested tubulin as a potential target. Docking study provided a structural insight into the interaction between 5m and tubulin. In summary, our study presents a drug repurposing case that redirects a cardiovascular agent to an anti-melanoma agent.

A facile and efficient method for synthesis of β-iodocarboxylates from terminal epoxides

A facile and efficient method has been developed for synthesis of β-iodocarboxylates in the presences of Ph3P/I2. Starting from epoxides, a series of β-iodocarboxylate compounds can be directly obtained in toluene media with excellent yields. Moreover, the method was successfully applied for the late-stage modification of natural products, such as isosteviol and vincamine derivatives, achieving the corresponding β-iodocarboxylates in good yields.

Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors

We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine-1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor.

A biphenyl type process for the preparation of a glycidyl ether (by machine translation)

The purpose of this invention is to offer a kind of through the epoxy bromo propane and couplet phenol compound under phase transfer catalyst in the reactive diluent is obtained by reacting biphenyl glycidyl ether synthesis method. Characterized in that according to the following steps : (1) the biphenol compounds and sodium carbonate according to the molar ratio of the 1 [...] 1.2 by adding to the reaction vessel, in 65-70 °C stirring under 10 hours, a supernatant liquid 2nd-step reaction. (2) a certain amount of obtained product and catalyst is added to the reaction flask, propane takes the epoxy bromine -by-drip through the constant pressure dropping funnel to the reaction flask with stirring, in 70-80 °C stirring under 4-7 hours, separating and purifying, that is, to obtain the product. The product obtained by this invention the epoxy reactive diluent, a chlorine-containing compound stabilizer, such as fabric finishing agent has wide application. Furthermore, it is also for synthesizing many industrial products: such as antistatic agent, emulsifier, plastic additives, cosmetics, an important intermediate of surface active agents and the like. (by machine translation)

Nonpeptidic propargylamines as inhibitors of lysine specific demethylase 1 (LSD1) with cellular activity

Lysine demethylases play an important role in epigenetic regulation and thus in the development of diseases like cancer or neurodegenerative disorders. As the lysine specific demethylase 1 (LSD1/KDM1) has been strongly connected to androgen and estrogen dependent gene expression, it serves as a promising target for the therapy of hormone dependent cancer. Here, we report on the discovery of new small molecule inhibitors of LSD1 containing a propargylamine warhead, starting out from lysine containing substrate analogues. On the basis of these substrate mimicking inhibitors, we were able to increase potency by a combination of similarity-based virtual screening and subsequent synthetic optimization resulting in more druglike LSD1 inhibitors that led to histone hypermethylation in breast cancer cells.

Synthesis and structure-activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for β-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC 50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier.

Novel aminoalcohol derivatives bearing 4-phenylphenol as antischistosomal drugs

There is a need to develop new antischistosomal compounds when the only available therapeutic agents praziquantel large-scale used in the world. A series of novel aminoalcohol derivatives bearing 4-phenylphenol moiety were designed and synthesized. The structures of all the newly synthesized compounds were identified by elemental analysis, 1H-NMR, 13C-NMR and LC-MS. Their biological activities were evaluated against Schistosoma japonicum in mice by an oral route. Among these compounds, in vivo, at concentrations 400mg/kg of mouse, compound 1-(biphenyl-4′-yloxy)-3-(1′-(3′, 4′-difluorophenyl)ethylamino)propan-2-ol (3j) produced the highest activity with 93.0% deparasitization. These compounds may find usefulness in the discovery and development of new antischistosomal drugs.

Analysis of β-amino alcohols as inhibitors of the potential anti-tubercular target N-acetyltransferase

The synthesis and inhibitory potencies of a novel series of β-amino alcohols, based on the hit-compound 3-[3′-(4″-cyclopent-2?- en-1?-ylphenoxy)-2′-hydroxypropyl]-5,5 dimethylimidazolidine-2,4- dione as specific inhibitors of mycobacterial N-acetyltransferase (NAT) enzymes are reported. Effects of synthesised compounds on growth of Mycobacterium tuberculosis have been determined.

SUBSTITUTED DIHYDRO AND TETRAHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF

The present invention relates to a series of substituted dihydro and tetrahydro oxazolopyrimidinones, specifically, to a series of 2-substituted-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-ones and 2-substituted-2,3,5,6-tetra-hydro-oxazolo[3,2-a]pyrimidin-7-ones of formula (I): Wherein p, n, X, Y, R1, R2, R3, R4, R5, R6, R7 and R8 are as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

Azolidines as beta-3 adrenergic receptor agonists

This invention provides compounds of Formula I having the structure wherein, A, X, Y, Z, W, R1, R2, R3, R4, R5, and R6 are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.