23975-60-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-CHLOROPHENYL)-4,4,4-TRIFLUOROBUTANE-1,3-DIONE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-CHLOROPHENYL)-4,4,4-TRIFLUOROBUTANE-1,3-DIONE is utilized as an intermediate in the production of agrochemicals. Its properties make it suitable for the creation of compounds that can be used in pest control and crop protection, thereby supporting agricultural productivity.
Used as a Precursor in Organic Reactions:
1-(2-CHLOROPHENYL)-4,4,4-TRIFLUOROBUTANE-1,3-DIONE is used as a precursor in a variety of organic reactions. Its reactivity and structural features enable it to participate in multiple chemical processes, facilitating the synthesis of a range of organic compounds.
Used in the Synthesis of Complex Chemical Compounds:
As a building block, 1-(2-CHLOROPHENYL)-4,4,4-TRIFLUOROBUTANE-1,3-DIONE is instrumental in the synthesis of more complex chemical compounds. Its integration into larger molecular structures is crucial for the development of advanced materials and specialty chemicals across various industries.

Upstream product

• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 50878-84-7 1-(2-chlorophenyl)-2-diazoethan-1-one 
• 118-91-2 ortho-chlorobenzoic acid 
• 1260243-02-4 ethyl 5-(2-chlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 

Relevant academic research and scientific papers

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.

NOVEL COMPOUNDS AS ROR GAMMA MODULATORS

The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring B, L, R1, R2, R3, R4, R5, Ra, Rb, n, m, p and q are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORγt). These compounds prevent, inhibit, or suppress the action of RORγt and are therefore useful in the treatment of RORγt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer.

A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis

This work reports the construction of cyclopentene cores from 1,6-enynes and aryl diazo ketones through two new reaction sequences involving initial gold-catalyzed cyclization of 1,6-enynes with diazo species, followed by rhodium-catalyzed skeletal rearrangement of the resulting 3-cyclopropyl-2-en-1-ones. In most instances the rhodium-catalyzed reactions afforded cyclopentene derivatives whereas several n-alkyl- or ortho-substituted phenyl ketones delivered seven-membered oxacycles. A plausible mechanism provides rationales for these two distinct products. (Figure presented.).

Synthesis, fungicidal activity and mode of action of 4-phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea

Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22) were synthesized, and their structures were confirmed by 1H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA), and compound III-3 on potato dextrose agar (PDA) indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM) and transmission electron micrography (TEM) were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

Synthesis and characterization of the titanium complexes bearing two β-enaminoketonato ligands with electron withdrawing groups/modified phenyls and their behaviors for ethylene (co-)polymerization

A series of new titanium complexes with two asymmetric bidentate β-enaminoketonato [N,O] ligands (2b-t), [PhNC(CF3)CHC(Ar)O] 2TiCl2 (2b, Ar = -C6H4F(o); 2c, Ar = -C6H4F(m); 2d, Ar = -C6H4F(p); 2e, Ar = -C6H4Cl(p); 2f, Ar = -C6H 4OMe(p); 2g, Ar = -C6H4CF3(p); 2h, Ar = -C6H4CF3(m); 2i, Ar = -C6H 4CF3(o); 2j, Ar = -C6H4Cl(o); 2k, Ar = -C6H4Br(o); 2l, Ar = -C6H4I(o); 2m, Ar = -C6H3F2(2,4); 2n, Ar = -C 6H3F2(2,6); 2o, Ar = -C6H 3F2(3,4); 2p, Ar = -C6H3F 2(3,5); 2q, Ar = -C6F5; 2r, Ar = C 6F4OMe; 2s, Ar = -C6H3Cl 2(2,6); 2t, Ar = -C6H3Cl2(2,5)), have been synthesized based on substituted acetophenones. X-Ray analyses reveal that complexes 2h, 2k, 2m, and 2n adopt distorted octahedral geometry around the titanium center, in which the two chloride ligands are situated in the cis-orientation. 2s also adopts distorted octahedral geometry, but the two chloride ligands in it are situated in the trans-orientation due to the increase of the steric effect of the phenyl derived from the acetophenone. The influence of the substituent effects on catalyst performance, including catalytic activities and the molecular weight distribution of the polymers obtained, was investigated in detail. With modified methylaluminoxane (MMAO) as a cocatalyst, complexes 2b-r and 2t are active catalysts for ethylene polymerization at room temperature, and produce high molecular weight polymers. It is observed that the catalytic activities are significantly enhanced by introducing some electron-withdrawing groups, such as -F, -Cl and -CF3, into the suitable positions of the phenyl ring close to the oxygen donor. It should be noted that complexes 2c-i, 2p, 2n and 2t are also capable of promoting the living copolymerization of ethylene with norbornene at room temperature, yielding high molecular weight copolymers with narrow molecular weight distributions (PDI = 1.05-1.30). The Royal Society of Chemistry 2010.

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.

Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors

Several chemical modifications in the N1-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro.

Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)- 3(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide (sc-58635, celecoxib)

A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC- 236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.