70627-20-2

Usage

Uses

Used in Organic Synthesis:
4-(2-Fluorobenzyloxy)benzaldehyde is used as a building block for the synthesis of various organic compounds due to its unique structure and reactivity. Its fluorine-substituted benzyl ether group allows for versatile chemical transformations, making it a valuable intermediate in the preparation of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(2-Fluorobenzyloxy)benzaldehyde is used as a key intermediate in the development of new drugs. Its unique structure and reactivity enable the synthesis of novel drug candidates with potential therapeutic applications. FBOB has been studied for its potential role in the development of drugs targeting various diseases and conditions.
Used in Material Science:
4-(2-Fluorobenzyloxy)benzaldehyde is also utilized in the field of material science for the development of new materials with specific properties. Its fluorine-substituted benzyl ether group can be incorporated into the design of advanced materials, such as polymers, coatings, and sensors, to impart desired characteristics.
Safety and Handling:
4-(2-Fluorobenzyloxy)benzaldehyde must be handled and stored according to standard chemical safety guidelines to ensure the safety of users and the environment. Proper protective equipment, such as gloves and eye protection, should be worn during handling, and the compound should be stored in a well-ventilated area, away from heat and direct sunlight.

InChI:InChI=1/C14H11FO2/c15-14-4-2-1-3-12(14)10-17-13-7-5-11(9-16)6-8-13/h1-9H,10H2

Upstream product

• 446-48-0 o-fluorobenzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 446-51-5 2-fluorobenzyl alcohol 
• 459-57-4 4-fluorobenzaldehyde 
• 345-35-7 2-fluorobenzyl chloride 

Downstream Products

• 955105-83-6 2-{(2,6-dioxocyclohexyl)[4-(2-fluorobenzyloxy)phenyl]methyl}cyclohexane-1,3-dione 
• 955105-87-0 2-{(4,4-dimethyl-2,6-dioxocyclohexyl)[4-(2-fluorobenzyloxy)phenyl]methyl}-5,5-dimethylcyclohexane-1,3-dione 
• 447456-63-5 13-[4-(2-fluorobenzyloxy)phenyl]-7,13-dihydro-12H-benzo[f]indeno[1,2-b]quinolin-12-one 
• 1218777-52-6 1-(3-pyridyl)-3-[4-(2-fluorobenzyloxy)phenyl]benzo[f]quinoline 
• 1000370-32-0 (S)-2-[4-(2-fluorobenzyloxy)benzylideneamino]propanamide 
• 1161738-33-5 (R)-2-[4-(2-fluorobenzyloxy)benzylideneamino]propanamide 
• 445466-16-0 1-methyl-3-[4(2-fluorobenzyloxy)phenyl]benzo[f]quinoline 
• 1131626-37-3 4-[4-(2-fluorobenzyloxy)phenyl]-2,3-dihydro-1H-cyclopenta[c]benzo[f]quinoline 

Relevant academic research and scientific papers

Difluoroketenimine: Generation from Difluorocarbene and Isocyanide and Its [3 + 2] Cycloadditions with Alkenes or Alkynes

Ketenimines have been explored as useful building blocks for the synthesis of heteroatom-containing cyclic compounds through the cycloaddition with polar multiple bonds. Herein, we report the cycloaddition of difluoroketenimine with nonpolar multiple bond

Discovery of highly potent and selective influenza virus neuraminidase inhibitors targeting 150-cavity

Encouraged by our earlier discovery of N1-selective inhibitors, the 150-cavity of influenza virus neuraminidases (NAs) could be further exploited to yield more potent oseltamivir derivatives. Herein, we report the design, synthesis and biological evaluation of a series of novel oseltamivir derivatives via the structural modifications at C5–NH2 of oseltamivir targeting 150-cavity. Among them, compound 5c bearing 4-(3-methoxybenzyloxy)benzyl group exhibited the most potent activity, which was lower or modestly improved activities than oseltamivir carboxylate (OSC) against N1 (H1N1), N1 (H5N1) and N1 (H5N1–H274Y). Specifically, there was 30-fold loss of activity against the wild-type strain H1N1. However, 5c displayed 4.85-fold more potent activity than OSC against H5N1–H274Y NA. Also, 5c demonstrated low cytotoxicity in vitro and no acute toxicity in mice. Molecular docking studies provided insights into the high potency of 5c against N1 and N1–H274Y mutant NAs. Besides, the in silico prediction of physicochemical properties and CYP enzymatic inhibitory ability of representative compounds were conducted to evaluate their drug-like properties.

Evolution of a 4-Benzyloxy-benzylamino Chemotype to Provide Efficacious, Potent, and Isoform Selective PPARα Agonists as Leads for Retinal Disorders

Peroxisome proliferator-activated receptor alpha (PPARα) is expressed in retinal Müller cells, endothelial cells, and in retinal pigment epithelium; agonism of PPARα with genetic or pharmacological tools ameliorates inflammation, vascular leakage, neurodegeneration, and neovascularization associated with retinal diseases in animal models. As such, PPARα is a promising drug target for diabetic retinopathy and age-related macular degeneration. Herein, we report proof-of-concept in vivo efficacy in an streptozotocin-induced vascular leakage model (rat) and preliminary pharmacokinetic assessment of a first-generation lead 4a (A91). Additionally, we present the design, synthesis, and evaluation of second-generation analogues, which led to the discovery of 4u and related compounds that reach cellular potencies 2,700-fold selectivity for PPARα over other PPAR isoforms. These studies identify a pipeline of candidates positioned for detailed PK/PD and pre-clinical evaluation.

AMIDE DERIVATIVES AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, formula (I) wherein R1. X, m. R2, Y, R3, Z, n, R4. A and B are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

NOVEL COMPOUNDS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1, X, m, R2, Y, R3, Z, n, R4, A and B are as defined in the specification, processes for their prep

Synthesis and analysis of anticonvulsant activities of new 4-[2-(4-alkoxybenzylamino)ethyl]-2H-1,2,4-triazol-3(4H)-one derivatives

The present study involved the design and synthesis of new substituted 4-[2-(4-alkoxybenzylamino) ethyl]-2H-1,2,4-triazol-3(4H)-one derivatives (8a-w) starting from 1,2-ethanediamine. The final compounds were screened for their in vivo anticonvulsant activities and neurotoxicities by maximal electroshock (MES) and rotarod tests, respectively. Among the compounds studied, 4-[2-(4-butoxybenzylamino)ethyl]-2H-1,2,4-triazol-3(4H)-one hydrochloride (8b) was found by intraperitoneal administration in mice to be the most potent compound with a median effective dose (ED50) value of 33.2 mg/kg and a high protective index (PI) value of 11.4. Compound 8b showed significant oral activity against MES-induced seizures in mice with an ED50 value of 83.1 mg/kg and a PI of 18.1. The results demonstrated that compound 8b possessed better anticonvulsant activity and higher safety than the marketed drug carbamazepine.

PROCESS FOR THE PRODUCTION OF 2-[4-(3- OR 2-FLUOROBENZYLOXY)BENZYLAMINO]PROPANAMIDES WITH HIGH PURITY DEGREE

A process for obtaining therapeutically active 2-[4-(3- and 2-(flurobenzyloxy)benzylamino]propanamides, and their salts with pharmaceutically acceptable acids with high purity degree, in particular, with a content of dibenzyl derivatives impurities lower

New PPARγ ligands based on 2-hydroxy-1,4-naphthoquinone: Computer-aided design, synthesis, and receptor-binding studies

FlexX-based molecular docking study was employed to identify 2-hydroxy-1,4-naphthoquinone as a new 'acidic head group' for the design of a novel series of PPARγ ligands. To provide the proof of concept, designed molecules were synthesized and evaluated in a standard radioligand-binding assay. Out of eight molecules, four were found to bind to the murine PPARγ with IC50 ranging from 0.2 to 56.2 μM as compared to standard pioglitazone, with IC50 of 0.7 μM.

PROCESS FOR THE PRODUCTION OF 2- [4 - ( 3- AND 2-FLU0R0BENZYL0XY) BENZYLAMIN0] PROPAN AMIDES

A process for obtaining therapeutically active 2-[4-(3- and 2- (fluorobenzyloxy)benzylamino]propanamides and their salts with pharmaceutically acceptable acids with high purity degree, in particular, with a content of dibenzyl derivatives impurities lower

Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof

This invention is related to carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones represented by Formula I: or a pharmaceutically acceptable salt or prodrug thereof, wherein: Y is oxygen or sulfur; R1, R21, R22 and R23 are independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl; or R22 and R23, together with the N, form a heterocycle; A1 and A2 are independently aryl, heteroaryl, saturated or partially unsaturated carbocycle or saturated or partially unsaturated heterocycle, any of which is optionally substituted; X is one or O, S, NR24, CR25R26, C(O), NR24C(O), C(O)NR24, SO, SO2 or a covalent bond; where R24, R25 and R26 are independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl. The invention also is directed to the use of carbocycle and heterocycle substituted semicarbazones and thiosemicarbazones for the treatment of neuronal damage following global and focal ischemia, for the treatment or prevention of neurodegenerative conditions such as amyotrophic lateral sclerosis (ALS), for the treatment and prevention of otoneurotoxicity and eye diseases involving glutamate toxicity and for the treatment, prevention or amelioration of pain, as anticonvulsants, and as antimanic depressants, as local anesthetics, as antiarrhythmics and for the treatment or prevention of diabetic neuropathy and urinary incontinence.