582-73-0

Basic information

• Product Name: 4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE
• Synonyms: AKOS MSC-0357;4,4,4-TRIFLUORO-1-(PYRIDINE-3-YL)BUTANE-1,3-DIONE;4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE;4,4,4-Trifluoro-1-(pyridine-3-yl)-1,3-butanedione;1-(3-Pyridyl)-4,4,4-trifluoro-1,3-butanedione;4,4,4-Trifluoro-1-(pyridin-3-yl)-1,3-butanedione;4,4,4-trifluoro-1-(3-pyridyl)-1,3-butanedione
• CAS NO: 582-73-0
• Molecular Formula: C₉H₆F₃NO₂
• Molecular Weight: 217.14
• Mol File: 582-73-0.mol

Chemical Properties

• Melting Point: 173-174°C
• Boiling Point: 276 °C at 760 mmHg
• Flash Point: 120.7 °C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 0.00792mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: 4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE(582-73-0)
• EPA Substance Registry System: 4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE(582-73-0)

Safety Data

• Hazardous Substances Data: 582-73-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE is used as a key intermediate in the synthesis of pharmaceuticals and agrochemicals for its ability to enhance the properties of these compounds.
Used in Chemical Research and Drug Development:
4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE serves as a reagent in chemical research and drug development, facilitating the discovery and creation of new chemical entities with potential therapeutic applications.
Used in Organic Chemistry:
4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE is used in the preparation of chiral ligands and catalysts, which are essential for enantioselective reactions and the production of enantiomerically pure compounds.
Used in Anti-Inflammatory and Antibacterial Applications:
Due to its potential anti-inflammatory and antibacterial properties, 4,4,4-TRIFLUORO-1-PYRIDIN-3-YLBUTANE-1,3-DIONE is being explored for use in the development of new treatments for inflammation and bacterial infections.

InChI:InChI=1/C9H6F3NO2/c10-9(11,12)8(15)4-7(14)6-2-1-3-13-5-6/h1-5,14H/b7-4-

Upstream product

• 350-03-8 methyl-3-pyridylketone 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 155557-13-4 2,2-difluoro-1-(pyridin-3-yl)ethanone 
• 1148055-42-8 C₁₆H₁₂F₃N₃OS 
• 1258207-56-5 C₁₅H₉F₃N₄O₂ 
• 940959-04-6 4-(5-pyridin-3-yl-3-trifluoromethyl-pyrazol-1-yl)-benzonitrile 
• 940959-05-7 4-(3-pyridin-3-yl-5-trifluoromethyl-pyrazol-1-yl)-benzonitrile 
• 940959-33-1 cyclohexanecarboxylic acid [5-(5-hydroxy-3-pyridin-3-yl-5-trifluoromethyl-4,5-dihydro-pyrazol-1-yl)-pyrazin-2-yl]-amide 
• 940959-03-5 4-(5-hydroxy-3-pyridin-3-yl-5-trifluorom,ethyl-4,5-dihydro-pyrazol-1-yl)-benzonitrile 

Relevant articles and documents

An SAR study of hydroxy-trifluoromethylpyrazolines as inhibitors of Orai1-mediated store operated Ca2+ entry in MDA-MB-231 breast cancer cells using a convenient Fluorescence Imaging Plate Reader assay

The proteins Orai1 and STIM1 control store-operated Ca2+ entry (SOCE) into cells. SOCE is important for migration, invasion and metastasis of MDA-MB-231 human triple negative breast cancer (TNBC) cells and has been proposed as a target for cancer drug discovery. Two hit compounds from a medium throughput screen, displayed encouraging inhibition of SOCE in MDA-MB-231 cells, as measured by a Fluorescence Imaging Plate Reader (FLIPR) Ca2+ assay. Following NMR spectroscopic analysis of these hits and reassignment of their structures as 5-hydroxy-5-trifluoromethylpyrazolines, a series of analogues was prepared via thermal condensation reactions between substituted acylhydrazones and trifluoromethyl 1,3-dicarbonyl arenes. Structure-activity relationship (SAR) studies showed that small lipophilic substituents at the 2- and 3-positions of the RHS and 2-, 3- and 4-postions of the LHS terminal benzene rings improved activity, resulting in a novel class of potent and selective inhibitors of SOCE.

One-pot synthesis of difluoromethyl ketones by a difluorination/fragmentation process

Difluoromethyl ketones are an under-studied class of ketones which have great potential as useful building blocks for materials and drug design. Here we report a simple and convenient synthesis of this class of compounds via a one-pot difluorination/fragm

Pyrazolo[1,5a]pyrimidines as a new class of FUSE binding protein 1 (FUBP1) inhibitors

The transcriptional regulator FUSE binding protein 1 (FUBP1) is aberrantly upregulated in various malignancies, fulfilling its oncogenic role by the deregulation of critical genes involved in cell cycle control and apoptosis regulation. Thus, the pharmaceutical inhibition of this protein would represent an encouraging novel targeted chemotherapy. Here, we demonstrate the identification and initial optimization of a pyrazolo[1,5a]pyrimidine-based FUBP1 inhibitor derived from medium throughput screening, which interferes with the binding of FUBP1 to its single stranded target DNA FUSE. We were able to generate a new class of FUBP1 interfering molecules with in vitro and biological activity. In biophysical assays, we could show that our best inhibitor, compound 6, potently inhibits the binding of FUBP1 to the FUSE sequence with an IC50value of 11.0 μM. Furthermore, hepatocellular carcinoma cells exhibited sensitivity towards the treatment with compound 6, resulting in reduced cell expansion and induction of cell death. Finally, we provide insights into the corresponding SAR landscape, leading to a prospective enhancement in potency and cellular efficacy.

Substituted pyrazoles as novel sEH antagonist: Investigation of key binding interactions within the catalytic domain

A novel series of pyrazole sEH inhibitors is reported. Lead optimization efforts to replace the aniline core are also described. In particular, 2-pyridine, 3-pyridine and pyridazine analogs are potent sEH inhibitors with favorable CYP3A4 inhibitory and microsomal stability profiles.

Interactions of aroyl- and heteroaroyltrifluoroacetones with thiobenzoylhydrazine

The interaction of aroyl(heteroaroyl)trifluoroacetones with thiobenzoylhydrazine may occur at both carbonyl groups. Reaction at the trifluoroacetyl group is facilitated by terminal substituents in the 1,3-dicarbonyl part, which leads can effectively conjugate with the adjacent carbonyl group. The products of condensation at the trifluoroacetyl group are 2-[2-aryl(heteroaroyl)-2-oxoethyl]-5-phenyl-2-trifluoromethyl-2,3-dihydro-1,3, 4-thiadiazoles, while condensation at the aroyl(heteroaroyl)group gave 3-aryl(heteroaryl)-5-hydroxy-1-thiobenzoyl-5-trifluoromethyl-4, 5-dihydro-1H-pyrazoles, which are not prone to tautomeric transformations in solution. 2008 Springer Science+Business Media, Inc.

SUBSTITUTED PYRAZOLE COMPOUNDS USEFUL AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS

Disclosed are compounds active against soluble epoxide hydrolase (sEH), compositions thereof and methods of using and making same.

Reaction of aroyl- and hetaroyltrifluoroacetones with acylhydrazines: Regioselectivity and tautomerism of the condensation products

Acylhydrazines react with 1,3-diketones of the general formula CF 3COCH2COR (where R is an aryl or hetaryl group) at both carbonyl groups. The reaction at the trifluoroacetyl group is favored by donor substituents in the aromatic ring of the 1,3-diketone or by the 2-furyl and, especially, 2-thienyl group as a hetaryl substituent, as well as by elevated temperature. The condensation products at the carbonyl group contiguous to the aryl or hetaryl ring have the structure of 5-hydroxy-4,5-dihydropyrazoles and do not undergo tautomeric transformations in solution. The condensation products at the trifluoroacetyl group have either 5-hydroxy-4,5-dihydropyrazole or hydrazone structure and give rise to ring-chain tautomeric equilibrium in solution. Electron-withdrawing substituents in the aromatic ring of the 1,3-dicarbonyl fragment and CDCl3 as solvent favor formation of the cyclic tautomer. The state of the tautomeric equilibrium is weakly sensitive to structural variations in the hydrazine component.

Synthesis and SAR/3D-QSAR studies on the COX-2 inhibitory activity of 1,5-diarylpyrazoles to validate the modified pharmacophore

Diverse analogs of 1,5-diarylpyrazoles having 3-hydroxymethyl-4-sulfamoyl (SO2NH2)/methyl sulfonyl (SO2Me)-pheny group at N1 were synthesized and evaluated for their in vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The SAR study mainly involved the variations at positions C-3, C-5 and N1 of the pyrazole ring. Several small hydrophobic groups at/around position-4 of C-5 phenyl, viz. 3,4-dimethylphenyl analog 9, 3-methyl-4-methylsulfanylphenyl analog 14 and 2,3-dihydrobenzo[b] thiophenyl analog 17, exhibited impressive COX-2 inhibitory potency. In general, the sulfonamide analogues with a CHF2 at C-3 were found to be more potent than those having a CF3 group. The three dimensional quantitative structure activity relationship comprising comparative molecular field analysis (3D-QSAR-CoMFA) afforded the models with high predictivity which further validated the acceptance of hydroxymethyl (CH2OH) group in the hydrophilic pocket of the COX-2 enzyme.

PYRAZOLO AND IMIDAZO-PYRIMIDINE DERIVATIVES

The present invention relates to novel pyrazolo- and imidazo-pyrimidine derivatives of formula (I) wherein A, D, E, L, M, Q, R1, R2 and R3 are as defined in the description and claims and to processes for their preparation, pharmaceutical compositions containing said derivatives and their use in the prevention and treatment of diseases.