59067-46-8

Usage

Uses

Used in Organic Synthesis:
4-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE is used as a key intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, facilitating the formation of desired products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE is used as a reagent in the synthesis of certain drugs and other fine chemicals. Its presence in these processes is crucial for the development of new medications and the improvement of existing ones.
Used in Chemical Reactions:
4-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE is employed as a reagent in a variety of chemical reactions, including oxidation, reduction, and condensation processes. Its versatility in these reactions makes it a valuable tool in the field of chemistry.
Safety Precautions:
It is important to handle 4-[(4-chlorobenzyl)oxy]benzaldehyde with care, as it may be toxic and harmful if ingested, inhaled, or comes into contact with the skin. Proper safety measures should be taken to minimize exposure and ensure the well-being of those working with 4-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE.

InChI:InChI=1/C14H11ClO2/c15-13-5-1-12(2-6-13)10-17-14-7-3-11(9-16)4-8-14/h1-9H,10H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 
• 99-96-7 4-hydroxy-benzoic acid 

Downstream Products

• 74649-82-4 ethyl 2-fluoro-3-<4-(4-chlorobenzyloxy)phenyl>acrylate 
• 85259-26-3 2-<4-(4-chlorobenzyloxy)phenyl>-2-hydroxyacetonitrile 
• 63608-10-6 4-(4-chlorobenzyloxy)benzyl alcohol 
• 1392418-65-3 C₂₄H₁₅ClF₃NO₄ 
• 1392418-47-1 C₃₀H₁₉ClF₃NO₄ 
• 1414806-63-5 (S,E)-2-(5-(4-(4-chlorobenzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 
• 1448816-02-1 C₅H₁₁NO*C₂₃H₂₁ClN₂O₅S 
• 896088-50-9 8-{4-[(4-chlorobenzyl)oxy]phenyl}-3-(2,4-dimethoxyphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile 
• 1448816-10-1 N-methylmorpholinium 4-[(4-chlorobenzyl)oxy]phenyl-3-cyano-6-oxo-1,4,5,6-tetrahydro-pyridine-2-thiolate 

Relevant academic research and scientific papers

Design, synthesis, biological evaluation and in silico study of benzyloxybenzaldehyde derivatives as selective aldh1a3 inhibitors

Aldehyde dehydrogenase 1A3 (ALDH1A3) has recently gained attention from researchers in the cancer field. Several studies have reported ALDH1A3 overexpression in different cancer types, which has been found to correlate with poor treatment recovery. Theref

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.

Synthesis and biological evaluation of tryptophan-derived rhodanine derivatives as PTP1B inhibitors and anti-bacterial agents

Several series of novel tryptophan-derived rhodanine derivatives were synthesized and identified as potential competitive PTP1B inhibitors and antibacterial agents. Among the compounds studied, 10b was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.36 ± 0.02 μM). In addition, the compounds also showed potent inhibition against other PTPs, especially CDC25B. Molecular docking analysis demonstrated that compounds 7c and 10b could occupy both the catalytic site and the adjacent pTyr binding site simultaneously. The compounds also showed higher levels of activity against gram-positive strains, the gram-negative strain Escherichia coli 1924, and multidrug-resistant gram-positive bacterial strains. Compounds 7c, 8c, 9e, 10a, and 10c had comparable or more potent antibacterial activity than the positive controls.

Sophoridine pyrrole, indole derivative and preparation method and application thereof

The invention relates to a sophoridine pyrrole, indole derivative. The invention discloses a chemical structure of the compound and further discloses a preparation method of the compound. In vitro anti-tumor activity researches show that anti-tumor drugs

Nitrogen-containing heterocyclic amide derivative and use thereof

The present invention discloses a nitrogen-containing heterocyclic amide derivative and use thereof, and in particular, the present invention relates to a novel class of nitrogen-containing heterocyclic amide derivatives and pharmaceutical compositions co

Novel cinnamic acid–tryptamine hybrids as potent butyrylcholinesterase inhibitors: Synthesis, biological evaluation, and docking study

A novel series of cinnamic acid–tryptamine hybrids was designed, synthesized, and evaluated as cholinesterase inhibitors. Anticholinesterase assays showed that all of the synthesized compounds displayed a clearly selective inhibition of butyrylcholinesterase (BChE), but only a moderate inhibitory effect toward acetylcholinesterase (AChE) was detected. Among these cinnamic acid–tryptamine hybrids, compound 7d was found to be the most potent inhibitor of BChE with an IC50 value of 0.55 ± 0.04 μM. This compound showed a 14-fold higher inhibitory potency than the standard drug donepezil (IC50 = 7.79 ± 0.81 μM) and inhibited BChE through a mixed-type inhibition mode. Moreover, a docking study revealed that compound 7d binds to both the catalytic anionic site (CAS) and the peripheral anionic site (PAS) of BChE. Also, compound 7d was evaluated against β-secretase, which exhibited low activity (inhibition percentage: 38%).

Structure-guided evolution of a 2-phenyl-4-carboxyquinoline chemotype into PPARα selective agonists: New leads for oculovascular conditions

Small molecule agonism of PPARα represents a promising new avenue for the development of non-invasive treatments for oculovascular diseases like diabetic retinopathy and age-related macular degeneration. Herein we report initial structure–activity relatio

An eco-friendly synthesis of 4-aryl-substituted pyrano-fuzed coumarins as potential pharmacological active heterocycles using molybdenum oxide nanoparticles as an effective and recyclable catalyst

A green cascade three-component reaction between 4-hydroxycoumarin, malononitrile and a wide range of arylaldehydes by employing molybdenum oxide nanoparticles (MoO3 NPs) is described. By this achievement, some medicinally important products have been successfully synthesized in a one-pot under green conditions. Obtaining good to excellent yields of products, environmentally benign procedure, being easily handled, availability of starting materials, use of non-toxic solvents, and high recyclability of nano-catalysts are the most important advantages of this methodology.

Ultrasound-assisted and efficient knoevenagel condensation reaction catalyzed by silica sodium carbonate nanoparticles

An efficient and ultrasound-assisted route to the synthesis of arylidene malononitriles/methylciano- or ethylciano acetates in a one-pot reaction catalyzed by silica sodium carbonate nanoparticles (SSC NPs) is described. In this reaction, SSC NPs demonstrated high efficiency as catalyst to obtain target products. By this achievement, a wide range of α,β-unsaturated compounds as Knoevenagel condensation products with good to excellent yields are obtained from reaction between numerous arylaldehydes, and malononitrile, methyl cianoacetate or ethyl cianoacetate. Target products which prepared in high yield and high purity can be candidate as important biologically active molecules. This method is an easy, cheap, rapid and highly efficient for the synthesis of desired products. In addition, capability of catalyst to separate from reaction mixture and reuse in further runs and being compatible with green chemistry are considered as other advantages of this procedure. All products were deduced from their FT-IR and FT-NMR spectroscopic and elemental analysis data.

Synthesis and biological evaluation of dihydrotriazine derivatives as potential antibacterial agents

A series of 1,4-dihydro-1,3,5-triazine derivatives were designed and synthesized and their antibacterial and antifungal activities were evaluated. Most of the synthesized compounds showed potent inhibition of several Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains, with minimum inhibitory concentrations (MICs) in the range of 2.1–181.2?μmol/L. Compounds 7a and 7c presented the most potent inhibitory activities against Gram-positive bacteria (e.g., Staphylococcus aureus 4220), Gram-negative bacteria (e.g., Escherichia coli 1924), and the fungus Candida albicans 7535, with MICs of 2.1 or 4.1?μmol/L. Especially, compound 7a was the most potent, with an MIC of 2.1?μmol/L against four multidrug-resistant, Gram-positive bacterial strains. The cytotoxic activity of the compound 7a, 7c and 7f was assessed in HepG2 cells, and the results suggest that 1,4-dihydro-1,3,5-triazine derivatives bearing a 6-benzyloxynaphthalen moiety are interesting scaffolds for the development of novel antibacterial agents.