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Usage

Uses

Used in Pharmaceutical Synthesis:
(Z)-1,1,1-trifluoro-4-hydroxy-4-(4-methylphenyl)-but-3-en-2-one is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique reactivity and electron-withdrawing nature facilitate the development of new medicinal compounds with improved efficacy and selectivity.
Used in Agrochemical Synthesis:
In the agrochemical industry, (Z)-1,1,1-trifluoro-4-hydroxy-4-(4-methylphenyl)-but-3-en-2-one is utilized as a building block for the creation of novel agrochemicals. Its properties allow for the design of more effective and targeted pesticides, herbicides, and other agricultural products.
Used in Organic Synthesis Research:
(Z)-1,1,1-trifluoro-4-hydroxy-4-(4-methylphenyl)-but-3-en-2-one is also used as a research tool in organic chemistry. Its distinctive structure makes it an interesting subject for studying reaction mechanisms, exploring new synthetic routes, and understanding the influence of electron-withdrawing groups on molecular properties.
Used in the Synthesis of Complex Organic Molecules:
Due to its unique structure and reactivity, (Z)-1,1,1-trifluoro-4-hydroxy-4-(4-methylphenyl)-but-3-en-2-one is employed in the synthesis of complex organic molecules. It serves as a versatile intermediate that can be further modified and functionalized to construct a wide range of organic compounds with diverse applications in various industries.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 122-00-9 para-methylacetophenone 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 678987-46-7 2-(hydroxymethyl)-4-[5-(4-methylphenyl)-3-(trifluoro-methyl)-1H-pyrazol-1-yl]benzenesulfonamide 

Relevant academic research and scientific papers

Structure–Activity Relationships of UTX-121 Derivatives for the Development of Novel Matrix Metalloproteinase-2/9 Inhibitors

Celecoxib, a nonsteroidal anti-inflammatory drug, has been reported to have antitumor and antimetastatic activities, and it has potential for application in cancer treatments. The expression of matrix metalloproteinase (MMP)-2/9 is strongly correlated wit

Synthesis and biological evaluation of salicylic acid analogues of celecoxib as a new class of selective cyclooxygenase-1 inhibitor

A series of salicylic acid analogues of celecoxib where the phenylsulfonamide moiety in the structure of celecoxib is replaced by salicylic acid moiety was synthesized and tested for in vitro cyclooxygenase (COX)-1 and COX-2 enzyme inhibition. Among the series, 5-substituted-2-hydroxy-benzoic acid analogues (7a–7h) generally showed better inhibitory activities on both enzymes than 4-substituted-2-hydroxy-ben-zoic acid analogues (12a–12h). In particular, the chloro analogue 7f which had the highest inhibitory effect (IC50=0.0057μM) to COX-1 with excellent COX-1 selectivity (SI=768) can be classified as a new potent and selective COX-1 inhibitor. The high inhibitory potency of 7f was rationalized through the docking simulation of this analogue in the active site of COX-1 enzyme.

Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Br?nsted Acids or Acidic Zeolites

The reaction of trifluoroacetyl alkynes [ArC≡C(C=O)CF3] with H2SO4 or TfOH affords products of addition of the acids to the acetylene bond. Hydrolysis of these adducts results in the formation of the corresponding 1,3-dike

2-Hydroxymethyl-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl] -1-benzenesulfonamide (DRF-4367): An orally active COX-2 inhibitor identified through pharmacophoric modulation

Analogs of 1,5-diarylpyrazoles with a novel pharmacophore at N1 were designed, synthesized and evaluated for the in-vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The variations at/around position-4 of the C-5 phenyl ring in conjunction with a CF3 and CHF2 groups at C-3 exhibited a high degree of potency and selectivity index (SI) for COX-2 inhibition. The in-vivo evaluation of these potent compounds with a few earlier ones indicated the 4-OMe-phenyl analog 6 and the 4-NHMe-phenyl analog 9 with a CF3, and the 4-OEt-phenyl analog 19 with a CHF2 group at C-3 to possess superior potency than celecoxib. In addition to its impressive anti-inflammatory, antipyretic, analgesic and anti-arthritic properties, compound 6 (DRF-4367) was found to possess an excellent pharmacokinetic profile, gastrointestinal (GI) safety in the long-term arthritis study and COX-2 potency in human whole blood assay. Thus, compound 6 was selected as an orally active anti-inflammatory candidate for pre-clinical evaluation.