18931-61-8

Usage

Uses

Used in Organic Synthesis:
1-(4-BROMO-PHENYL)-4,4,4-TRIFLUORO-BUTANE-1,3-DIONE is used as a building block in the synthesis of various pharmaceutical compounds due to its distinctive structure and reactivity. Its presence in the synthesis process can lead to the creation of new molecules with potential therapeutic properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(4-BROMO-PHENYL)-4,4,4-TRIFLUORO-BUTANE-1,3-DIONE is utilized as a reagent in organic reactions, contributing to the development of novel drug candidates. Its unique structural features make it a valuable component in the design and synthesis of new pharmaceutical agents.
Used in the Development of Fluorinated Organic Compounds:
The trifluoromethyl groups present in 1-(4-BROMO-PHENYL)-4,4,4-TRIFLUORO-BUTANE-1,3-DIONE make it a potentially valuable molecule in the field of fluorinated organic compounds. Fluorination is a common strategy in medicinal chemistry to enhance the pharmacokinetic and pharmacodynamic properties of drug molecules, and 1-(4-BROMO-PHENYL)-4,4,4-TRIFLUORO-BUTANE-1,3-DIONE can serve as a precursor in such endeavors.
Used in Materials Science:
The unique properties of 1-(4-BROMO-PHENYL)-4,4,4-TRIFLUORO-BUTANE-1,3-DIONE also make it a candidate for applications in materials science. Its structural attributes could be leveraged to develop new materials with specific properties, such as improved stability or reactivity, for use in various industrial applications.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 99-90-1 para-bromoacetophenone 
• 1546-79-8 N-trifluoroacetylimidazole 
• 431-47-0 trifluoroacetic acid-methyl ester 

Downstream Products

• 307531-59-5 1-(4-bromophenyl)-2-diazo-4,4,4-trifluorobutane-1,3-dione 
• 219986-60-4 3-(4-bromo-phenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-pyrazole-1-carbothioic acid amide 
• 328012-22-2 6-(4-bromophenyl)-3-cyano-4-trifluoromethyl-2(1H)-pyridone 
• 343262-54-4 5-Methylsulfonyl-2-[5-(4-bromophenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]pyridine 
• 678987-59-2 4-[5-(4-bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide 
• 586333-33-7 1-phenyl-3-(trifluoromethyl)-5-(4-bromophenyl)-1H-pyrazole 

Relevant academic research and scientific papers

N-(3-((4-trifluoromethyl)-2-pyrimidinyl)aminophenyl)-2,6-difluorobenzene sulfamide derivative

The invention discloses N-(3-((4-trifluoromethyl)-2-pyrimidinyl)aminophenyl)-2,6-difluorobenzene sulfamide having an anti-tumor activity and a derivative thereof, and synthesis methods thereof. The N-(3-((4-trifluoromethyl)-2-pyrimidinyl)aminophenyl)-2,6-difluorobenzene sulfamide has a structural formula as shown in Formula I. The synthesis method disclosed by the invention comprises the followingsteps: performing nucleophilic substitution on 2,6-difluorobenzenesulfonyl chloride and m-phenylenediamine to obtain sulfonamide; enabling an amino group of N-(3-aminophenyl)-2,6-difluorobenzene sulfamide to react with cyanamide to obtain guanidine salt; then preparing a series of different substituted 1,3-diketone compounds; finally, enabling the guanidine salt to react with 1,3-diketone to forma pyrimidine ring, and ingeniously introducing the anactive group of the pyrimidine ring into a molecular structure. According to the N-(3-((4-trifluoromethyl)-2-pyrimidinyl)aminophenyl)-2,6-difluorobenzene sulfamide and the synthesis method, the antitumor multiplication inhibition activity, the solubility and the like of a compound is adjusted by changing a substituent of the pyrimidine ring, and the compound has the advantage of simple and convenient adjustment.

An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors

Integrated continuous manufacturing has emerged as a promising device for the rapid manufacturing of active pharmaceutical ingredients (APIs). We herein report a newly designed continuous flow micro-total process system platform for the rapid manufacturing of celecoxib, a selective nonsteroidal anti-inflammatory drug. This approach has been proven generally for the synthesis of several alkyl and aryl substituted pyrazoles. In order to minimize the tedious work-up process of potential reaction intermediates/products, we have developed a continuous flow extraction and separation platform to carry out the entire reaction sequence resulting in a short residence time with good yield. The present process was further extended to gram-scale synthesis of the COX-2-related API, viz. celecoxib, in the continuous flow process.

Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors

In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.

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.

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

The discovery of an ultrafast cross-coupling of alkyl- and aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [11C]-labeled PET tracer celecoxib.

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.

Liver X Receptor (LXR) partial agonists: Biaryl pyrazoles and imidazoles displaying a preference for LXRβ

A series of biaryl pyrazole and imidazole Liver X Receptor (LXR) partial agonists has been synthesized displaying LXRβ selectivity. The LXRβ selective partial agonist 18 was identified with potent induction of ATP binding transporters ABCA1 and ABCG1 in human whole blood (EC50 = 1.2 μM, 55% efficacy). In mice 18 displayed peripheral induction of ABCA1 at 3 and 10 mpk doses with no significant elevation of plasma or hepatic triglycerides at these doses, showing an improved profile compared to a full pan-agonist.

LIVER X RECEPTOR (LXR) MODULATORS

Described herein are liver X receptor (LXR) modulators and methods of utilizing LXR modulators in the treatment of LXR-associated diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.

1,5-Diketones Synthesis via Three-Component Cascade Reaction

A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.

LIVER X RECEPTOR (LXR) MODULATORS FOR THE TREATMENT OF DERMAL DISEASES, DISORDERS AND CONDITIONS

Described herein are liver X receptor (LXR) modulators and methods of utilizing LXR modulators in the treatment of dermal diseases, disorders or conditions. Also described herein are pharmaceutical compositions containg such compounds.