26974-15-2

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
3-(TRIFLUOROMETHYL)-5-P-TOLYL-1H-PYRAZOLE is used as a key intermediate in the synthesis of new bioactive compounds. Its trifluoromethyl group is known to improve the biological activity of molecules, making it a valuable component in the creation of innovative drugs with enhanced therapeutic properties.
Used in Drug Design and Optimization:
In the pharmaceutical industry, 3-(TRIFLUOROMETHYL)-5-P-TOLYL-1H-PYRAZOLE serves as a structural and chemical feature for the design and optimization of new drugs. The p-tolyl group allows for further modification and fine-tuning of the compound's properties, enabling researchers to develop drugs with improved efficacy, selectivity, and safety profiles.

InChI:InChI=1/C11H9F3N2/c1-7-2-4-8(5-3-7)9-6-10(16-15-9)11(12,13)14/h2-6H,1H3,(H,15,16)

Upstream product

• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 104-87-0 4-methyl-benzaldehyde 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 720-94-5 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione 
• 4392-54-5 4-aminosulfonylphenylhydrazine 
• 701-34-8 4-bromo-benzenesulfonic acid amide 
• 53764-99-1 4,4,4-trifluoro-1-(3-methylbenzene)butane-1,3-dione 
• 2236129-81-8 trifluoroacetaldehyde N-triftosylhydrazone 
• 766-97-2 4-n-methylphenylacetylene 
• 122-00-9 para-methylacetophenone 
• 753-90-2 trifluoroethylamine 
• 96107-01-6 (E)-1,1,1,-trifluoro-4-(p-tolyl)but-3-en-2-one 

Downstream Products

• 1290697-33-4 5-(p-tolyl)-1H-pyrazole-3-carbonitrile 
• 169590-42-5 4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide 
• 853793-24-5 N,N-dibenzyl-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide 
• 515845-18-8 1-phenyl-5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazole 

Relevant academic research and scientific papers

Fragmenlt Recombination Design, Synthesis, and Safener Activity of Novel Ester-Substituted Pyrazole Derivatives

Fenoxaprop-p-ethyl (FE), a type of acetyl-CoA carboxylase (ACCase) inhibitor, has been extensively applied to a variety of crop plants. It can cause damage to wheat (Triticum aestivum) even resulting in the death of the crop. On the prerequisite of not reducing herbicidal efficiency on target weed species, herbicide safeners selectively protect crops from herbicide injury. Based on fragment splicing, a series of novel substituted pyrazole derivatives was designed to ultimately address the phytotoxicity to wheat caused by FE. The title compounds were synthesized in a one-pot way and characterized via infrared spectroscopy, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. The bioactivity assay proved that the FE phytotoxicity to wheat could be reduced by most of the title compounds. The molecular docking model indicated that compound IV-21 prevented fenoxaprop acid (FA) from reaching or acting with ACCase. The absorption, distribution, metabolism, excretion, and toxicity predictions demonstrated that compound IV-21 exhibited superior pharmacokinetic properties to the commercialized safener mefenpyr-diethyl. The current work revealed that a series of newly substituted pyrazole derivatives presented strong herbicide safener activity in wheat. This may serve as a potential candidate structure to contribute to the further protection of wheat from herbicide injury.

One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis

An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.

Synthetic method of celecoxib

The invention provides a synthetic route and a preparation method of celecoxib. According to the method, hydrazine hydrate which is low in price and easy to obtain is used as a raw material in the first-step reaction, green and environment-friendly water is used as a solvent, the synthesis yield is high, and aftertreatment is easy and convenient, in the second-step reaction, a compound shown as the formula IV is prepared through aromatic nucleophilic substitution reaction (SNAr), so that the use of a heavy metal catalyst is avoided, the selectivity is high, the generation of byproducts of position isomerism is reduced, and the yield is relatively high. The method has the advantages of simple operation, convenient separation and purification of each step, high yield and good product quality, and can be used for large-scale industrial preparation of the celecoxib.

Pyrazole derivative compound, and preparation method and application thereof

The invention belongs to the technical field of medicine synthesis, and particularly relates to a pyrazole derivative compound, and a preparation method and an application thereof. The polysubstitutedpyrazole compound disclosed by the invention has a structure represented by a formula (I), wherein R1, R2 and R3 in the formula are respectively defined in the specification. The invention also relates to an agricultural composition containing the compound or the pharmaceutically acceptable salt thereof. The prepared compound has good safener activity, can well relieve the toxicity of herbicidesto crops after being used, and is beneficial to the growth of crops. Compared with similar compounds, the compound provided by the invention shows good detoxification effect and safety.

Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene

A general and practical strategy for 3-trifluoromethylpyrazole synthesis is reported that occurs by the three-component coupling of environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP), aldehydes, and sulfonyl hydrazides. This highly regioselective three-component reaction is metal-free, catalyst-free, and operationally simple and features mild conditions, a broad substrate scope, high yields, and valuable functional group tolerance. Remarkably, the reactions could be performed on a 100 mmol scale and smoothly afforded the key intermediates for the synthesis of celecoxib, mavacoxib, SC-560, and AS-136A. Preliminary mechanism studies indicated that a 1,3-hydrogen atom transfer process was involved in this transformation.

Cycloaddition of Trifluoroacetaldehyde N-Triftosylhydrazone (TFHZ-Tfs) with Alkynes for Synthesizing 3-Trifluoromethylpyrazoles

A transition-metal-free [3 + 2] cycloaddition between trifluoroacetaldehyde N-triftosylhydrazone (TFHZ-Tfs) and alkynes is reported. This protocol provides an operationally simple and general method for the synthesis of diverse 3-trifluoromethylpyrazoles in good to excellent yields with broad substrate scope, including aryl, heteroaryl, and alkyl terminal alkynes, and electron-deficient internal alkynes. The synthetic potential of this method was further demonstrated by the synthesis of an antiarthritic drug Celecoxib in multigram scale.

Trifluoromethyl substituted pyrazole derivative as 3- well as synthesis method and application thereof (by machine translation)

The invention belongs to, the technical field. of synthesis of medical materials, 3 - and particularly, 2 - relates to a method for mixing and reacting a compound with, an, 2 - organic solvent I through Colecoxib a, method of mixing reaction with an organ

Synthetic method of novel trifluoromethyl pyrazole compound

The invention belongs to the technical field of organic synthesis chemistry, and relates to a synthetic method of a trifluoromethyl pyrazole compound. The compound can be used for synthesizing a variety of drugs, pesticides and bioactive molecules, so that synthesis and application of the compound are focused. According to the preparation method disclosed by the invention, a simple easily-available raw material acetylene compound and N-trifluoroacetaldehyde phenylsulfonyl hydrazone are used for efficiently synthesizing the three-dimensional specific trifluoromethyl pyrazole compound by one step under a condition without metal catalysis. The method disclosed by the invention has the characteristics that the raw materials are simple and easily available, the range is wide, metal catalysts are not needed, massive synthesis is achieved, the operation method is simple, the reaction is efficient, and the product has a specific three-dimensional structure; and industrial synthesis can be realized.

Design, synthesis and biological evaluation of novel hydroxamic acid based histone deacetylase 6 selective inhibitors bearing phenylpyrazol scaffold as surface recognition motif

In recent years, inhibition of HDAC6 became a promising therapeutic strategy for the treatment of cancer and HDAC6 inhibitors were considered to be potent anti-cancer agents. In this work, celecoxib showed moderate degree of HDAC6 inhibition activity and selectivity in preliminary enzyme inhibition activity assay. A series of hydroxamic acid derivatives bearing phenylpyrazol moiety were designed and synthesized as HDAC6 inhibitors. Most compounds showed potent HDAC6 inhibition activity. 11i was the most selective compound against HDAC6 with IC50 values of 0.020 μM and selective factor of 101.1. Structure-activity relationship analysis indicated that locating the linker group at 1′ of pyrazol gave the most selectivity. The most compounds 11i (GI50 = 3.63 μM) exhibited 6-fold more potent than vorinostat in HepG2 cells. Considering of the high selectivity against HDAC6 and anti-proliferation activity, such compounds have potential to be developed as anti-cancer agents.

With anti-tumor activity of phenyl hydroxamic acid compounds and use thereof (by machine translation)

The invention belongs to the field of medical technology, relates to a with anti-tumor activity of phenyl hydroxamic acid compounds, and in particular to the 3 (5) - substituted phenyl - 5 (3) - substituted pyrazole fragment phenyl hydroxamic acid compounds, and their pharmaceutically acceptable salt, hydrate, and the compound as the active ingredient of the pharmaceutical composition, and the preparation of histone deacetylase inhibitors and their use for the treatment and/or prevention of cancer. The compound of the following structure: wherein R1 Independently selected from one or more of the following substituents: halogen, (C1 - C4) alkyl, dioxo methylene; R2 Is independently selected from (C1 - C4) alkyl, halo (C1 - C4) alkyl, substituted or unsubstituted phenyl, said substituent is (C1 - C4) alkyl; n is 0 - 2 is an integer between. (by machine translation)