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 
• 78178-57-1 3-(4-(benzyloxy)phenyl)-3-oxopropanoic acid 
• 917-64-6 methyl magnesium iodide 
• 52805-36-4 4-benzyloxybenzonitrile 
• 13031-43-1 4-acetyloxyacetophenone 
• 149683-53-4 4-(tert-butyldimethylsilyloxy)acetophenone 
• 220820-79-1 5-[2-(4-hydroxy-phenyl)-2-methyl-[1,3]dithian-4-yl]-pentanoic acid 
• 100-51-6 benzyl alcohol 
• 7601-90-3 perchloric acid 
• 946-80-5 (benzyloxy)benzene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 36438-63-8 1-(4-[benzyloxy]phenyl)ethan-1-ol 
• 194787-92-3 N-(4-benzyloxy-phenacyl)-acetamide 
• 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 
• 95556-68-6 cis-2-Methyl-3-<4-benzyloxy-phenyl>-buten-(2)-saeure-(1)-ethylester 
• 95556-68-6 trans-2-Methyl-3-<4-benzyloxy-phenyl>-buten-(2)-saeure-(1)-ethylester 
• 106281-26-9 α-(p-benzyloxyphenyl)-α-methylfurfuryl alcohol 
• 111361-00-3 (E)-1-(4-Benzyloxy-phenyl)-3-pyridin-2-yl-propenone 
• 77503-08-3 4-(1,1-Bis-ethylsulfanyl-ethyl)-phenol 
• 154479-30-8 (E)-1-(4-(benzyloxy)phenyl)-3-(4-fluorophenyl)prop-2-en-1-one 
• 154479-31-9 (E)-1-(4-(benzyloxy)phenyl)-3-(4-chlorophenyl)prop-2-en-1-one 
• 154479-29-5 (E)-1-(4-(benzyloxy)phenyl)-3-phenylprop-2-en-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.

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.

Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.

Compound for treating diabetes and/or related disorders

The invention discloses a compound for treating diabetes and/or related disorders, specifically a method for preventing, inhibiting and/or reversing amylin amyloid fibril formation, preventing isletsof Langerhans beta-cell death, preventing and/or reversing conversion of soluble human amylin to insoluble human amylin, and preventing and inhibiting and/or reversing cytotoxic amylin fibril formation. The invention also relates to a compound for preparing drugs for preventing and/or treating amylin amyloid-associated diseases.

COMPOUNDS FOR TREATING DIABETES AND/OR RELATED CONDITIONS

Compounds useful for treating or preventing diabetes and related conditions, and for preventing, inhibiting or reversing amylin-amyloid fibril formation, preventing islets of Langerhans (Beta)-cell death, preventing or reversing the transition from soluble human amylin to insoluble human amylin, preventing and inhibiting or reversing cytotoxic amylin fibril formation. The invention relates to compounds of Formula (I) and compounds of Formula (II): (Formulae (I) and (II)).