22179-86-8

Usage

Uses

Used in Pharmaceutical Industry:
4-(TRIFLUOROMETHYL)BENZAMIDOXIME is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block in the synthesis of various molecules with potential therapeutic applications.
Used in Anticancer Applications:
In the field of oncology, 4-(TRIFLUOROMETHYL)BENZAMIDOXIME is used as a key intermediate in the synthesis of 5-(3-chlorothiophen-2-yl)-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazole, a potential anticancer agent. 4-(TRIFLUOROMETHYL)BENZAMIDOXIME may exhibit inhibitory effects on tumor growth and progression, making it a promising candidate for further research and development in cancer treatment.

InChI:InChI=1/C8H7F3N2O/c9-8(10,11)6-3-1-5(2-4-6)7(12)13-14/h1-4,14H,(H2,12,13)

Upstream product

• 455-18-5 4-CF₃C₆H₄CN 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 66046-34-2 4-(trifluoromethyl)benzaldehyde oxime 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 131472-28-1 4-trifluoromethylbenzamidine 
• 478488-87-8 5-(3,4,5-Trichloro-thiophen-2-yl)-3-(4-trifluoromethyl-phenyl)-[1,2,4]-oxadiazole 
• 1206808-72-1 5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol 
• 1206808-82-3 5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol 
• 1206809-03-1 1-(2,3-dichloro-4-((3-(4-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)-2-methylenebutan-1-one 
• 38980-96-0 4-(trifluoromethyl)benzimidamide hydrochloride 
• 40067-75-2 3,3'-bis-(4-trifluoromethyl-phenyl)-5,5'-m-phenylene-bis-[1,2,4]oxadiazole 
• 206882-64-6 2-(4-trifluoromethylphenyl)-4-methylpyrimidine 3-oxide 

Relevant academic research and scientific papers

Computer-aided identification, synthesis, and biological evaluation of novel inhibitors for botulinum neurotoxin serotype A

Botulinum neurotoxins (BoNTs) are among the most potent biological toxin known to humans, and are classified as Category A bioterrorism agents by the Centers for Disease Control and prevention (CDC). There are seven known BoNT serotypes (A-G) which have b

Novel O-acylated amidoximes and substituted 1,2,4-oxadiazoles synthesised from (+)-ketopinic acid possessing potent virus-inhibiting activity against phylogenetically distinct influenza A viruses

This article describes the synthesis and antiviral activity evaluation of new substituted 1,2,4-oxadiazoles containing a bicyclic substituent at position 5 of the heterocycle and O-acylated amidoximes as precursors for their synthesis. New compounds were

Synthesis, spectroscopic characterization and DNA/HSA binding studies of (phenyl/naphthyl)ethenyl-substituted 1,3,4-oxadiazolyl-1,2,4-oxadiazoles

Two new series of conjugated arylethenyl-1,3,4-oxadiazolyl-1,2,4-oxadiazoles were obtained and spectroscopically characterized in terms of UV-Vis absorption, fluorescence and interaction with CT-DNA and Human Serum Albumin (HSA) biomolecules. Phenyl- and 1-naphthyl-bearing examples were analysed, and the spectroscopic properties of its substitution series were compared, showing extensive conjugation in all compounds and absorption differences due to both the aryl-ethenyl subunit and substituted phenyl/phenylene at the 1,2,4-oxadiazole side. Strong binding interactions of the obtained compounds with CT-DNA and moderate HSA-association capability were observed spectroscopically, and further docking studies were performed. This journal is

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

INHIBITOR COMPOUNDS

The disclosure relates to heterocyclic compounds and methods for their preparation. The disclosure provides compounds that may have beneficial therapeutic activity in the treatment of a disease or condition mediated by excessive or otherwise undesirable Des1 and/or fibrotic activity.

Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds

Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

The alarming increase in multi- and extensively drug-resistant (MDR and XDR) strains of Mycobacterium tuberculosis (MTB) has triggered the scientific community to search for novel, effective, and safer therapeutics. To this end, a series of 3,5-disubstitu

Syntheses and biological activity of platinum(II) and palladium(II) complexes with phenyl-oxadiazole-ethylenediamine ligands

This work describes the synthesis, characterization, cytotoxicity and antibacterial activity of three ligands derived from phenyl-oxadiazole-ethylenediamine and their platinum(II) and palladium(II) complexes. These compounds were characterized by elemental analysis, and Raman, IR, and NMR spectroscopies. We have prepared complexes with different substituents on the aromatic ring to provide influence in the antibacterial activity and cytotoxicity. The antibacterial activity was evaluated against Gram-positive bacteria Staphylococcus aureus (ATCC 25213), Staphylococcus epidermidis (ATCC 12228) and Gram-negative bacteria Escherichia coli (ATCC 11229) and Pseudomonas aeruginosa (ATCC 27853). The cytotoxicity was evaluated in two different tumor cell lines: mouse metastatic mammary adenocarcinoma (4T1), and murine colon cancer cells (CT26WT), and a non-tumor cell Baby Hamster Kidney (BHK-21). Based on the results obtained for the antibacterial and the cytotoxic activity it is possible to conclude that the presence of metal and groups NO2 and CF3 contributed to antibacterial activity with low cytotoxicity.

Beyond direct Nrf2 activation; reinvestigating 1,2,4-oxadiazole scaffold as a master key unlocking the antioxidant cellular machinery for cancer therapy

Harnessing the antioxidant cellular machinery has sparked considerable interest as an efficient anticancer strategy. Activating Nrf2, the master switch of the cellular redox system, suppresses ROS, alleviates oxidative stress, and halts cancer progression

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py