5067-21-0

Usage

General Description

1,3-Propanedione, 1-(3-chlorophenyl)-3-(2-hydroxyphenyl)- is a chemical compound that consists of a 1,3-propanedione backbone with a 3-chlorophenyl group and a 2-hydroxyphenyl group attached. It is a ketone compound that may be used in various industrial and laboratory applications, including as a precursor in the synthesis of pharmaceuticals, agrochemicals, and fragrances. The 3-chlorophenyl and 2-hydroxyphenyl groups can impart specific chemical and physical properties to the compound, making it useful in a range of different applications. However, it is important to handle this chemical with care due to its potential hazards and toxicological properties.

Upstream product

• 4010-23-5 2-acetylphenyl 3-chlorobenzoate 
• 118-93-4 o-hydroxyacetophenone 
• 618-46-2 m-Chlorobenzoyl chloride 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 136764-63-1 3'-Chloro-3-hydroxy-2-methoxyflavanone 
• 134051-35-7 1a,7a-Dihydro-1a-(3-chlorophenyl)-7H-oxireno<1>benzopyran-7-one 
• 84634-55-9 2-(2'-hydroxyphenyl)-4-m-chlorophenyl-1,5-benzodiazepine 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease

Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.

Pharmacophore and docking-based hierarchical virtual screening for the designing of aldose reductase inhibitors: Synthesis and biological evaluation

A set of 54 studied flavonoid inhibitors of aldose reductase (ALR2) enzyme has been utilized for pharmacophore modeling and 3D-QSAR analysis using "PHASE" program of Schr?dinger software. The generated pharmacophore model (AADRR.1109) was challenged to screen "PHASE" database to identify new ALR2 inhibitors. The retrieved hits were employed for docking analysis and pharmacokinetic parameter calculation to obtain orally active molecules. To predict the activity of final retrieved hits, 3D-QSAR model was developed, and the best model was selected on the basis of various statistical parameters (Rtrain 2 0.719; Q test 2 0.647 and SD 0.663). Totally five screened molecules which showed better enhanced predicted activity were synthesized and evaluated for in vitro ALR2 inhibitory activity. All tested molecules showed ALR2 inhibitory activity (IC50) below 40 μM. Additionally, the free radical scavenging potential of synthesized molecules was also determined which played a useful role to control the progression of diabetic complications. All molecules showed good antioxidant potential, thus the designed molecules, in future, could be explored to ameliorate the development of diabetic complications.

Mild and efficient organocatalytic method for the synthesis of flavones

A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.

Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands.

Epoxidation of Flavones by Dimethyldioxirane

The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported.These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C,H analyses.Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n.Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f, as a mixture of cis and trans isomers.

Reactions of Carbonyl Compounds in Basic Solutions. Part 11. The Baker-Venkataraman Rearrangement

The detailed mechanism of the Baker-Venkataraman rearrangement has been studied.The kinetics of the rearrangement of a series of 2-acetylphenyl 3- or 4-substituted benzoates and acetylnaphthyl benzoates catalysed by a basic 'non-nucleophilic' buffer in dimethyl sulphoxide have been measured.Studies of substituent effects, kinetic isotope effects, and acidity function correlations indicate a pathway involving pre-equilibrium formation of the carbanion, followed by rate-determining intramolecular nucleophilic attack.The methanolysis of the 2-acetylphenyl benzoates catalysed by methoxide in methanolic dimethyl sulphoxide has been similary investigated.In this case the pathway appears to involve neighbouring group participation by the ketonic carbonyl group.

2-(2'-Hydroxyphenyl)-4-aryl-1,5-benzodiazepines as CNS active agents

1-Aryl-3(2'-hydroxyphenyl)-propane-1,3-diones (III) have been prepared by the Baker-Venkataraman transformation of the corresponding 2-substituted benzoyloxyacetophenones (II). The aforesaid propane-1,3-diones (III) were condensed with o-phenylene diamine