76193-67-4

Basic information

• Product Name: 4-BENZYLOXY-BENZALDEHYDE OXIME
• Synonyms: N-{[4-(benzyloxy)phenyl]Methylidene}hydroxylaMine;Benzaldehyde,4-(phenylMethoxy)-, oxiMe;(E)-N-{[4-(benzyloxy)phenyl]methylidene}hydroxylamine
• CAS NO: 76193-67-4
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.26
• Mol File: 76193-67-4.mol

Chemical Properties

• Boiling Point: 371.5°C at 760 mmHg
• Flash Point: 178.5°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 3.55E-06mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: 4-BENZYLOXY-BENZALDEHYDE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-BENZALDEHYDE OXIME(76193-67-4)
• EPA Substance Registry System: 4-BENZYLOXY-BENZALDEHYDE OXIME(76193-67-4)

Safety Data

• Hazardous Substances Data: 76193-67-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Benzyloxy-benzaldehyde oxime is utilized as a reagent in organic synthesis for the preparation of a range of nitrogen-containing compounds. Its unique structure allows for the creation of diverse chemical entities, making it a valuable component in the synthesis process.
Used in Pharmaceutical Applications:
Due to its anti-inflammatory and analgesic properties, 4-benzyloxy-benzaldehyde oxime is considered a potential candidate for pharmaceutical development. Its ability to alleviate pain and reduce inflammation positions it as a promising substance for the treatment of various conditions.
Used in Agriculture and Pest Control:
4-Benzyloxy-benzaldehyde oxime has demonstrated activity as an insecticide, indicating its potential use in agricultural and pest control industries. This property makes it a candidate for developing new and effective pest management solutions to protect crops and maintain agricultural productivity.

InChI:InChI=1/C14H13NO2/c16-15-10-12-6-8-14(9-7-12)17-11-13-4-2-1-3-5-13/h1-10,16H,11H2/b15-10+

Upstream product

• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 699-06-9 4-hydroxybenzaldehyde oxime 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 106328-89-6 N-Acetoxy-N-(4-benzyloxy-benzyl)-acetamide 
• 883749-85-7 [3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol 
• 1020849-68-6 1-(4-benzyloxyphenyl)-4-(nitromethyl)benzene 
• 1449421-94-6 3-(4-(benzyloxy)phenyl)-5,6-dimethylbenzo[d]isoxazole-4,7-diol 
• 1242296-33-8 carbamic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester 
• 167098-81-9 3-[4-(benzyloxy)phenyl]-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide 
• 1210761-18-4 ethyl 3-(4-(benzyloxy)phenyl)isoxazole-5-carboxylate 
• 698348-95-7 C₁₄H₁₁NO₂ 
• 1204423-98-2 [3-(4-Benzyloxyphenyl)-4-methylisoxazol-5-yl]methanol 
• 161975-22-0 4-(benzyloxy) benzothioamide 
• 76193-68-5 2-(4-benzyloxybenzyl)-1,4-dihydro-6-methoxy-7-benzyloxy-3-(2H)-isoquinolone 

Relevant articles and documents

Design, synthesis, in vitro and in silico evaluation of new 3-phenyl-4,5-dihydroisoxazole-5-carboxamides active against drug-resistant mycobacterium tuberculosis

A new series of 3-phenyl-4,5-dihydroisoxazole-5-carboxamides were designed, synthesized, and evaluated for their potency against Mtb H37Rv. Designed molecules were synthesized by one-pot cycloaddition reaction in good to excellent yields. Anti-Tubercular evaluation of all synthesized derivatives identified 6k to be highly potent (MIC 1 μg/mL) against Mtb and drug-resistant strains. All potent derivatives were found to be non-toxic when tested against Vero cells. Also, in silico studies were employed to explore the binding patterns of designed compounds to target Mycobacterial membrane protein Large-3. All derivatives exhibited excellent binding patterns with the receptor. The excellent in silico Absorption, Distribution, Metabolism, and Excretion properties and druggability parameters positions these molecules as promising lead candidates for the future development of new drugs to treat drug-resistant Tuberculosis.

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles

A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.

Synthesis of novel 2H-chromene-3-carboxylate isoxazole/isoxazoline derivatives via 1,3-dipolar cycloaddition reaction (NOAC)

Synthesis of novel (3-phenylisoxazol-5-yl)methyl-2H-chromene-3-carboxylates (7a–7d) and (3-phenyl-4,5-dihydroisoxazol-5-yl)methyl-2H-chromene-3-carboxylates (8a–8p) by 1,3-dipolar cycloaddition, and nitrile oxide and alkyne cycloaddition (NOAC) is presented. The products are characterised by IR, 1H and 13C NMR, and ESI-MS data.

Design and synthesis of neolamellarin a derivatives targeting heat shock protein 90

In this study, we designed and synthesized a novel family of neolamellarin A derivatives that showed high inhibitory activity toward heat shock protein 90 (Hsp90), a kinase associated with cell proliferation. The 3,4-bis(catechol)pyrrole scaffold and the benzyl group with methoxy modification at N position of pyrrole are essential to the Hsp90 inhibitory activity and cytotoxicity of these compounds. Western blot analysis demonstrated that these compounds induced dramatic depletion of the examined client proteins of Hsp90, and accelerated cancer cell apoptosis. Docking simulations suggested that the binding mode of 9p was similar to that of the VER49009, a potent inhibitor of Hsp90. Further molecular dynamics simulation indicated that the hydrophobic interactions as well as the hydrogen bonds contributed to the high affinity of 9p to Hsp90.

Synthesis of new dithiolethione and methanethiosulfonate systems endowed with pharmaceutical interest

Here we report synthetic methodology affording in the most efficient way the rapid preparation of new dithiolethiones (DTTs) and methanethiosulfonates (MTSs). These were evaluated as STAT3 inhibitors since these electrophilic systems could react with thio

Pharmaceutical composition for inhibiting apoptosis of neuron or neurodegeneration

Provided is a pharmaceutical composition for inhibiting apoptosis of neurons or neurodegeneration. The pharmaceutical composition effectively prevents or treats diseases related to apoptosis of neurons or neurodegeneration.

Design, synthesis, and evaluation of hydroxamic acid derivatives as promising agents for the management of Chagas disease

Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5-dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g) was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to 1 μM). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.