70627-17-7

Usage

Uses

Used in Pharmaceutical Industry:
4-[(2,4-DICHLOROBENZYL)OXY]BENZALDEHYDE is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and enhance the properties of existing ones.
Used in Agrochemical Industry:
In the agrochemical sector, 4-[(2,4-DICHLOROBENZYL)OXY]BENZALDEHYDE is utilized as a component in the production of agrochemicals, potentially improving the effectiveness of pesticides and other agricultural chemicals.
Used in Organic Synthesis:
4-[(2,4-DICHLOROBENZYL)OXY]BENZALDEHYDE is used as a building block in organic synthesis, allowing for the creation of a wide range of chemical compounds for various purposes.
Used in Fragrance and Flavoring Industry:
4-[(2,4-DICHLOROBENZYL)OXY]BENZALDEHYDE is used as a component in the formulation of fragrances and flavoring ingredients due to the presence of benzaldehyde groups, which contribute to its aromatic properties.
Used in Disinfectants and Preservatives:
4-[(2,4-DICHLOROBENZYL)OXY]BENZALDEHYDE is used in the development of disinfectants and preservatives, capitalizing on the antimicrobial and antiseptic properties conferred by the chlorobenzyl group in its structure.

InChI:InChI=1/C14H10Cl2O2/c15-12-4-3-11(14(16)7-12)9-18-13-5-1-10(8-17)2-6-13/h1-8H,9H2

Upstream product

• 94-99-5 2,4-Dichlorobenzyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 20443-99-6 2,4-dichlorobenzyl bromide 

Downstream Products

• 1414806-65-7 (S,E)-2-(5-(4-(2,4-dichlorobenzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 
• 302564-39-2 C₁₅H₁₃Cl₂N₃OS 
• 1240307-31-6 1-(4-((2,4-dichlorobenzyl)oxy)benzyl)azetidine-3-carboxylic acid 
• 1334929-02-0 (E)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(4-(2,4-dichlorobenzyloxy)phenyl)prop-2-en-1-one 
• 1334928-93-6 (E)-1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-(2,4-dichlorobenzyloxy)phenyl)prop-2-en-1-one 
• 1334929-37-1 (E)-1,3-bis(4-(2,4-dichlorobenzyloxy)phenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

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.

Biological evaluation and in silico molecular docking study of a new series of thiazol-2-yl-hydrazone conglomerates

A new series of hybridized thiazol-2-yl-hydrazone derivatives having diverse substituents were designed, synthesized, and screened for their anti-inflammatory property by a carrageenan-induced paw edema method. The compounds 11a, 11b, 11c, 11d, 11e, 11g, 11m and 11p revealed significant inhibition when compared to Diclofenac sodium. Subsequently, two highly potent compounds (11d and 11e) were evaluated for their cytotoxic effect on the tumor cell line. The binding interactions of thiazol-2-yl-hydrazones with the cyclooxygenase-2 (COX-2) protein (PDB: 3LN1) displayed effective interactions with Arg-120, Tyr-385 and Tyr-355 amino acids, the main criteria of the COX-2 inhibitor. In addition, all the compounds showed moderate to good in vitro antibacterial activity. Most active benzyloxy derivatives were also tested to understand the radical scavenging efficacy by the 2,2-diphenyl-1-picrylhydrazyl method. Graphical Abstract: [Figure not available: see fulltext.].

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

Quinazoline derivatives as selective CYP1B1 inhibitors

CYP1B1 is implicated to have a role in the development of breast, ovarian, renal, skin and lung carcinomas. It has been suggested that identification of potent and specific CYP1B1 inhibitors can lead to a novel treatment of cancer. Flavonoids have a compact rigid skeleton which fit precisely within the binding cavity of CYP1B1. Systematic isosteric replacement of flavonoid ‘O’ atom with ‘N’ atom led to the prediction that a ‘quinazoline’ scaffold could be the basis for designing potential CYP1B1 inhibitors. A total of 20 quinazoline analogs were synthesized and screened for CYP1B1 and CYP1A1 inhibition in Sacchrosomes. IC50 determinations of six compounds with capability of inhibiting CYP1B1 identified quinazolines 5c and 5h as the best candidates for CYP1B1 inhibition, with IC50 values in the nM range. Further selectivity studies with homologous CYPs, belonging to the CYP1, CYP2 and CYP3 family of enzymes, showed that the compounds are likely to be free from critical drug-drug interaction liability. Molecular modelling studies were performed to rationalize the observed enzymatic inhibitions. Further biological studies in live yeast and human cells, harboring CYP1A1 and CYP1B1 enzymes, have illustrated the most potent compounds' cellular permeability and capability of potently inhibiting CYP1B1 enzyme expressed within live cells.

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.

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.

Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone

Four novel series of compounds, including the l-phenylalanine-derived C5-substituted rhodanine (6a-q, 7a-j) and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone (9a-e, 11a-e) have been designed, synthesized, characterized, and evaluated for their antibacterial activity. Some of these compounds showed significant antibacterial activity against Gram-positive bacterias, especially against the strains of multidrug-resistant clinical isolates, among which compounds 6c-e, 6g, 6i, 6j and 6q exhibiting high levels of antimicrobial activity against Staphylococcus aureus RN4220 with minimum inhibitory concentration (MIC) values of 2 μg/mL. Compound 6q showed the most potent activity of all of the compounds against all of the test multidrug-resistant clinical isolates tested. Unfortunately, however, none of the compounds were active against Gram-negative bacteria at 64 μg/mL.

Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv

A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 μg/mL

Selective and potent monoamine oxidase type B inhibitors: substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones

The synthesis and the evaluation of the monoamine oxidase A and B inhibitory activities of 21 new substituted acylhydrazones of various aromatic aldehydes and 4-(benzyloxy)acetophenone, and four substituted semicarbazones of benzaldehyde and 4-(benzyloxy)benzaldehyde, are described.The 4-(benzyloxy)phenyl group contributing to a high lipophilicity led to the most active compounds.One of these, compound 3g (IC50 = 3 nM, MAO A/MAO B selectivity > 33 000), was found to act as a revervible and probably tight-binding inhibitor.The studied acyclic hydrazones and semicarbazones are structurally related to other reversible and potent inhibitors, eg, heterocyclic compounds such as 1,3,4-oxadiazol-2(3H)-one derivatives in which the hydrazono group is intracyclic.Some of these new inhibitors might find use in the symptomatic treatment of neurodegenerative processes.MAO B inhibitor / hydrazone (aromatic acyl-) / semicarbazone (aromatic)