55579-73-2

Usage

Uses

Used in Medicinal Chemistry:
5-(2-Trifluoromethyl-phenyl)-cyclohexane-1,3-dione is used as a building block for the synthesis of bioactive molecules, contributing to the development of new pharmaceutical compounds.
Used in Organic Synthesis:
5-(2-TRIFLUOROMETHYL-PHENYL)-CYCLOHEXANE-1,3-DIONE serves as a reagent in organic synthesis, facilitating the creation of various chemical compounds with potential applications across different industries.
Used as a Precursor in Pharmaceutical Compound Preparation:
5-(2-Trifluoromethyl-phenyl)-cyclohexane-1,3-dione is utilized as a precursor in the preparation of pharmaceutical compounds, aiding in the advancement of drug discovery and development processes.
Used in Drug Discovery and Development:
5-(2-TRIFLUOROMETHYL-PHENYL)-CYCLOHEXANE-1,3-DIONE's enhanced lipophilicity and metabolic stability, due to the presence of the trifluoromethyl group, make it a valuable tool in drug discovery and development, potentially leading to the creation of more effective and stable pharmaceuticals.

InChI:InChI=1/C13H11F3O2/c14-13(15,16)12-4-2-1-3-11(12)8-5-9(17)7-10(18)6-8/h1-4,8H,5-7H2

Upstream product

• 76293-37-3 2-trifluoromethylbenzalacetone 
• 105-53-3 diethyl malonate 
• 447-61-0 2-Trifluoromethylbenzaldehyde 

Downstream Products

• 55579-51-6 7-chloro-10-hydroxy-1-oxo-3-(2-trifluoromethylphenyl)-1,2,3,4-tetrahydro-9(10H)-acridone 
• 144128-62-1 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-3-(2-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one 
• 144155-04-4 7-Chloro-3-(2-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione 

Relevant academic research and scientific papers

Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC50 of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS.

PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE CYCLIC ENAMINONE DERIVATIVES

A process for the production of optically active cyclic enaminone derivatives characterized by aminating one of the carbonyl groups of a cyclic 1,3-diketone derivative having a symmetry plane to obtain an optically isomeric mixture of chiral cyclic enamin

Synthesis and Antimalarial Properties of 1-Imino Derivatives of 7-Chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and Related Structures

To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates.Among structural modifications prepared, including N10-alkyl and C2-substituted analogs, removal of the C9 oxygen, and introduction of an imino side chain at C9, the imines of the N10-H acridinediones were the most active compounds obtained.The imino derivative of7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.