54696-05-8

Usage

Chemical Properties

white to cream crystalline powder

Preparation

Obtained by reaction of benzyl chloride with 4-hydroxyacetophenone in the presence of KOH in acetonitrile. Then, the mixture was refluxed for 3 h.

InChI:InChI=1/C15H14O2/c1-12(16)14-7-9-15(10-8-14)17-11-13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 100-44-7 benzyl chloride 
• 99-93-4 4-Hydroxyacetophenone 
• 100-39-0 benzyl bromide 
• 13031-43-1 4-acetyloxyacetophenone 
• 149683-53-4 4-(tert-butyldimethylsilyloxy)acetophenone 
• 7601-90-3 perchloric acid 
• 946-80-5 (benzyloxy)benzene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 75-52-5 nitromethane 
• 75-36-5 acetyl chloride 
• 4254-67-5 2-bromo-1-(4-benzyloxyphenyl)-1-ethanone 
• 99-90-1 para-bromoacetophenone 
• 100-51-6 benzyl alcohol 

Downstream Products

• 53090-45-2 ethyl 3-[4-(benzyloxy)phenyl]-3-oxopropanoate 
• 66742-43-6 [1-(4-Benzyloxy-phenyl)-ethyl]-(3-ethoxy-propyl)-amine 
• 38110-32-6 (E)-3-(4-Benzyloxy-phenyl)-but-2-enoic acid methyl ester 
• 4254-67-5 2-bromo-1-(4-benzyloxyphenyl)-1-ethanone 
• 106281-26-9 α-(p-benzyloxyphenyl)-α-methylfurfuryl alcohol 
• 142472-13-7 1-(4-benzyloxyphenyl)-3-phenyl-1,3-propanedione 
• 76937-64-9 1-(4-Benzyloxy-2-methoxy-phenyl)-3-(4-benzyloxy-phenyl)-propane-1,3-dione 
• 99481-22-8 2-<4-(4-benzyloxyphenyl)-3-pentenyl>-2-methyl-1,3-dioxolane 
• 122399-83-1 3-(4-benzyloxybenzoyl)-2-hydroxypropionic acid 
• 63365-56-0 1-(4-(benzyloxy)phenyl)-2-chloroethanone 
• 99-93-4 4-Hydroxyacetophenone 
• 157953-15-6 1-(4-benzyloxy-3-iodophenyl)ethanone 
• 51345-81-4 1-<4-(benzyloxy)phenyl>-3-piperidinopropan-1-one 
• 51345-83-6 1-<4-(benzyloxy)phenyl>-3-morpholinopropan-1-one 

Relevant academic research and scientific papers

Europium complex of 5-(4-dodecyloxyphenyl)2,2’-bipyridine-6’-carboxylic acid

Based on ‘1,2,4-triazine’ methodology, a new lanthanide(III) ligand, 5-(4-dodecyloxyphenyl)-2,2’-bipyridine-6’-carboxylic acid, was synthesized, and its luminescent europium(III) complex was prepared. The solubility in organic solvents for both the ligand

Simple heteroaryl modifications in the 4,5-diarylisoxazol-3-carboxylic acid scaffold favorably modulates the activity as dual mPGES-1/5-LO inhibitors with in vivo efficacy

Microsomal prostaglandin E2 synthase-1 (mPGES-1), 5-lipoxygenase (5-LO) and 5- lipoxygenase-activating protein (FLAP) are key for biosynthesis of proinflammatory lipid mediators and pharmacologically relevant drug targets. In the present study, we made an attempt to explore the role of small heteroaromatic fragments on the 4,5-diarylisoxazol-3-carboxylic acid scaffold, which are selected to interact with focused regions in the active sites of mPGES-1, 5-LO and FLAP. We report that the simple structural variations on the benzyloxyaryl side-arm of the scaffold significantly influence the selectivity against mPGES-1, 5-LO and FLAP, enabling to produce multi-target inhibitors of these protein targets, exemplified by compound 18 (IC50 mPGES-1 = 0.16 μM; IC50 5-LO = 0.39 μM) with in vivo efficacy in animal model of inflammation. The computationally modeled binding structures of these new inhibitors for three targets provide clues for rational design of modified structures as multi-target inhibitors. In conclusion, the simple synthetic procedure, and the possibility of enhancing the potency of this class of inhibitors through structural modifications pave the way for further development of new multi-target inhibitors against mPGES-1, 5-LO and FLAP, with potential application as anti-inflammatory agents.

Discovery of Resorcinol-Based Polycyclic Structures as Tyrosinase Inhibitors for Treatment of Parkinson’s Disease

Tyrosinase is involved in the synthesis of neuromelanin in the substantia nigra, which is closely correlated with the pathogenesis of Parkinson’s disease. Herein, we identified S05014 (l-Tyr, IC50 = 6.25 ± 1.43 nM; l-Dopa, IC50 = 0.6

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Apoptosis: A target for anticancer therapy with novel cyanopyridines

One of the many methods of treating cancer is to terminate the uncontrolled growth of cancer cells. So, aiming the apoptotic pathway is an exciting approach to finding new anticancer agents. A novel series of cyanopyridines was designed and synthesized for antiproliferative evaluation. 2-Amino-6-(4-(benzyloxy)phenyl)-4-(4-(dimethylamino)phenyl) nicotinonitrile 10f was the most potent inhibitor against the growth of PC-3, and HepG-2 cancer cell lines with IC50 values of 2.04 uM (selectivity index, SI = 78.63, 43, respectively). Also, 10f was safe against the growth of normal human diploid lung fibroblasts cell line (WI-38) with an IC50 value of 160.04 uM. Its analogs, 10b, 10d, 10g, and 11b, were also active against the growth of PC-3, and HepG-2 while against MCF-7 cell line, they displayed good cytotoxic activity compared to the reference standard 5-FU. Remarkably, mechanistic studies indicated that compounds 10b, 10d, 10f, 10g, and 11b stimulated the level of active caspase 3 and boosted the BAX/BCL2 ratio 20–95 folds in comparison to the control. Our results have also indicated that 10b, 10d, 10f, 10g, and 11b exhibited a very potent inhibitory activity against PIM-1 kinase enzyme, where the IC50 values unraveled very potent molecules in the micromolar range (0.47–1.27 μM). Further investigations have shown that 10f, the most potent PIM-1 kinase inhibitor, induced a cell cycle arrest at the G2/M phase. Moreover, in silico evaluation of ADME properties indicated that all the cyanopyridine compounds are orally bioavailable with no permeation to the blood brain barrier.

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.

HETEROCYCLIC COMPOUNDS AS MUTANT IDH INHIBITORS

The present disclosure relates generally to compounds useful in treatment of conditions associated with mutant isocitrate dehydrogenase (mt-IDH), particularly mutant IDH1 enzymes. Specifically, the present invention discloses compound of formula (IA), which exhibits inhibitory activity against mutant IDH1 enzymes. Method of treating conditions associated with excessive activity of mutant IDH1 enzymes with such compound is disclosed. Uses thereof, pharmaceutical composition, and kits are also disclosed.

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.