37074-39-8

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-methylacetophenone is used as a reactant for the preparation of benzimidazolones, which are selective peroxisome proliferator activated receptor gamma (PPARγ) modulators. These modulators play a crucial role in regulating cellular differentiation, inflammation, and lipid metabolism, making them potential therapeutic agents for the treatment of various diseases, including diabetes, obesity, and cardiovascular disorders.
In the synthesis of benzimidazolones, 4-chloro-3-methylacetophenone serves as a starting material, which undergoes a series of chemical reactions to form the desired active compounds. The introduction of the chlorine and methyl groups at specific positions on the benzene ring contributes to the modulation of the compound's biological activity and selectivity towards PPARγ.
Furthermore, the reactivity of 4-chloro-3-methylacetophenone allows for the development of novel chemical entities with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects. This makes it an essential component in the ongoing research and development of new drugs targeting PPARγ and other related pathways.

Upstream product

• 95-49-8 2-methylchlorobenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 201230-82-2 carbon monoxide 
• 594-27-4 tetramethylstannane 
• 65610-03-9 4-chloro-3-methyl phenacyl chloride 
• 7697-29-2 4-chloro-3-methylbenzoic acid 
• 917-54-4 methyllithium 

Downstream Products

• 103038-95-5 2-(4-chloro-3-methylphenyl)-1,2-propene 
• 7697-29-2 4-chloro-3-methylbenzoic acid 
• 2845-85-4 4-chloroisophthalic acid 
• 102877-28-1 1-(4-chloro-3-methyl-phenyl)-ethanol 
• 803633-66-1 4-Chlor-α-isopropylamino-3-methyl-acetophenon 
• 186682-37-1 2-[1-(4-Chloro-3-methyl-phenyl)-eth-(E)-ylidene]-3-cyclohex-1-enyl-succinic acid 1-ethyl ester 
• 205178-80-9 2-Bromo-1-(4-chloro-3-methylphenyl)ethan-1-one 
• 475471-20-6 4-(4-chloro-3-methylphenyl)-2,4-dioxobutyric acid ethyl ester 
• 861965-07-3 1-(4-chloro-3-methylphenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one 
• 877994-55-3 5-(4-chloro-3-methyl-phenyl)-1H-pyrazole-3-carbonyl chloride 
• 113342-32-8 5-(4-chloro-3-methylphenyl)-1-H-pyrazole-3-carboxylic acid 
• 192702-07-1 5-(4-chloro-3-methyl-phenyl)-1-[(4-methylphenyl)methyl]-1H-pyrazole-3-carboxylic acid 
• 192703-20-1 1-(4-methylbenzyl)-5-(4-chloro-3-methylphenyl)pyrazole-3-carboxylic acid chloride 
• 475471-21-7 N-[(1S)-endo-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl]-5-(4-chloro-3-methyl-phenyl)-1-H-pyrazole-3-carboxamide 

Relevant academic research and scientific papers

Biaryl Benzylamine Derivatives

The present invention relates to biaryl-benzylamine compounds, to processes for their production, to their use as pharmaceuticals and to pharmaceutical compositions comprising them.

Molecular modeling, structure-activity relationships and functional antagonism studies of 4-hydroxy-1-methyl-4-(4-methylphenyl)-3-piperidyl 4-methylphenyl ketones as a novel class of dopamine transporter inhibitors

We previously disclosed the discovery of 4-hydroxy-1-methyl-4-(4-methylphenyl)-3-piperidyl 4-methylphenyl ketone (3) as a novel class of dopamine transporter (DAT) inhibitors and showed that (±)-3 has a significant functional antagonism against cocaine in vitro. Our previous preliminary structure-activity relationship study led to identification of a more potent DAT inhibitor [(±)-4] but this compound failed to show any significant functional antagonism. To search for more potent analogues than 3 but still displaying significant functional antagonism, further SARs, molecular modeling studies and in vitro pharmacological evaluation of this novel class of DAT inhibitors were performed. Sixteen new analogues were synthesized in racemic form and evaluated as DAT inhibitors. It was found that seven new analogues are reasonably potent DAT inhibitors with Ki values of 0.041-0.30 and 0.052-0.16μM in [3H]mazindol binding and inhibition of DA reuptake. Chiral isomers of several potent DAT inhibitors were obtained through chiral HPLC separation and evaluated as inhibitors at all the three monoamine transporter sites. In general, the (-)- isomer is more active than the (+)-isomer in inhibition of DA reuptake and all the (-)-isomers are selective inhibitors at the DAT site. Evaluation of cocaine's effect on dopamine uptake in the presence and absence of (+)-3 and (-)-3 showed that (-)-3 is responsible for the functional antagonism obtained with the origin lead (±)-3 in binding and inhibition of DA reuptake, appeared to have improved functional antagonism as compared to (±)-3. Copyright

Practical synthesis of acetophenones from phenoltriflates

A new practical method for the preparation of acetophenone from aryl triflates is reported. The acyl group is installed by a mixture of SnMe4, Pd(0) and CO (balloon), using a three-component procedure.