98386-81-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(TRIFLUOROMETHYL)CINNAMIC ACID is used as a building block for the synthesis of various drugs and biologically active compounds, due to its versatile chemical properties and potential therapeutic effects.
Used in Organic Synthesis:
2-(TRIFLUOROMETHYL)CINNAMIC ACID is used as a reagent for introducing a trifluoromethyl group into a molecule, leveraging its strong electron-withdrawing properties to enhance the molecule's characteristics and reactivity.
Used in Anti-inflammatory Applications:
2-(TRIFLUOROMETHYL)CINNAMIC ACID is studied for its potential anti-inflammatory properties, which could be beneficial in the development of treatments for various inflammatory conditions.
Used in Antioxidant Applications:
2-(TRIFLUOROMETHYL)CINNAMIC ACID is also being investigated for its antioxidant properties, which may contribute to the prevention or treatment of oxidative stress-related diseases.

InChI:InChI=1/C10H7F3O2/c11-10(12,13)8(9(14)15)6-7-4-2-1-3-5-7/h1-6H,(H,14,15)/b8-6-

Upstream product

• 141-82-2 malonic acid 
• 123486-66-8 3-<2'-(trifluoromethyl)phenyl>-2-propenal 
• 444-29-1 2-iodo(trifluoromethyl)benzene 
• 447-61-0 2-Trifluoromethylbenzaldehyde 

Downstream Products

• 1476043-86-3 (E)-N-(2-amino-4-fluorophenyl)-3-(2-(trifluoromethyl)phenyl)acrylamide 
• 1476043-87-4 (E)-5-fluoro-2-(2-(trifluoromethyl)styryl)-1H-benzo[d]imidazole 
• 1476043-88-5 (E)-N-(2-amino-4-methylphenyl)-3-(2-(trifluoromethyl)phenyl)acrylamide 
• 1476043-89-6 (E)-5-methyl-2-(2-(trifluoromethyl)styryl)-1H-benzo[d]imidazole 
• 1476043-90-9 (E)-N-(2-amino-4-chlorophenyl)-3-(2-(trifluoromethyl)phenyl)acrylamide 
• 1476043-91-0 (E)-5-chloro-2-(2-(trifluoromethyl)styryl)-1H-benzo[d]imidazole 
• 1476043-92-1 (E)-N-(2-amino-4-methoxyphenyl)-3-(2-(trifluoromethyl)phenyl)acrylamide 
• 1476043-93-2 (E)-5-methoxy-2-(2-(trifluoromethyl)styryl)-1H-benzo[d]imidazole 
• 1476043-67-0 (E)-N-(2-aminophenyl)-3-(2-trifluoromethylphenyl)acrylamide 
• 1476043-68-1 (E)-2-(2-(trifluoromethyl)styryl)-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.

The potential role of the 5,6-dihydropyridin-2(1: H)-one unit of piperlongumine on the anticancer activity

Piperlongumine (PL), a potent anticancer agent from the plant long pepper (Piper longum), contains the 5,6-dihydropyridin-2(1H)-one heterocyclic scaffold and cinnamoyl unit. In this paper, we synthesized a series of PL analogs and evaluated their cytotoxicity against cancer cells for the sake of exploring which pharmacophore plays a more potent role in enhancing the anticancer activities of PL. These results illustrated that the position effect, not the electronic effect, of substituents plays a certain role in the cytotoxicity of PL and its analogs. More important, the 5,6-dihydropyridin-2(1H)-one unit, a potent pharmacophore in enhancing the antiproliferative activities of PL, could react with cysteamine and lead to ROS generation, and then bring about the occurrence of ROS-induced downstream events, followed by cell cycle arrest and apoptosis. This work suggests that introducing a lactam unit containing Michael acceptors may be a potent strategy to enhancing the anticancer activity of drugs. This journal is

Developing piperlongumine-directed glutathione S-transferase inhibitors by an electrophilicity-based strategy

We report a case of successful design of glutathione S-transferase (GST) inhibitors via a natural product-inspired and electrophilicity-based strategy. Based on this strategy, a novel piperlongumine analog (PL-13) bearing a para-trifluoromethyl group and an α-chlorine on its aromatic and lactam rings, respectively, surfaced as a promising GST inhibitor, thereby overcoming cisplatin resistance in lung cancer A549 cells.

Hydroxamic acids block replication of hepatitis c virus

Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase

Novel imatinib amide derivatives (a1-28, b1-9) were synthesized and evaluated for their biological activities. All compounds were characterized by 1H NMR, MS and elemental analysis. Among all the derivatives, compounds a4, a10, a21, b1 and b2 displayed the most significant ability of inhibiting K562 cell proliferation with the IC50 values of 0.67, 0.66, 0.65, 0.59 and 0.62 μM, respectively, indicating that these compounds were potent inhibitors of Bcr-Abl in leukemic K562 cells, comparable to the reference compound imatinib. Molecular docking study was performed to position compounds a21 and b1 into the active site of Abl to determine the probable binding modes

Design, synthesis and biological evaluation of cinnamic acyl shikonin derivatives

Inducing apoptosis is an important and promising therapeutic approach to overcome cancer. Here, we described a series of novel synthesized compounds, cinnamic acyl shikonin derivatives (1b-19b), which were synthesized starting from shikonin and cinnamic acids, which exhibit anticancer activity via inducing apoptosis in vitro. Our flow cytometry results showed that compound 8b((E)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent -3-enyl-3-(3-(trifluoromethyl) phenyl)acrylate) (IC50=0.69, 0.65, 1.62 μm for human SW872-s, A875 and A549 cell lines, respectively) exhibited conspicuous anticancer activities and has low cell toxicity in vitro. Therefore, we considered that compound 8b is potentially to be a candidate of anticancer agent. The proliferation inhibitory effect of compound 8b was associated with its apoptosis-inducing effect by activating caspase-3, caspase-7, caspase-9, and PARP. When the level of cleaved caspase-3, cleaved caspase-7, cleaved caspase-9, and cleaved PARP are rise, apoptosis of cancer cells will be induced.

PHARMACEUTICALLY ACTIVE BENZOXAZOLE, BENZTHIAZOLE AND BENZIMIDAZOLE ACID DERIVATIVES

Compounds of formula (I): wherein R1, R2 and R3 are independently, hydrogen, halogen, CF3, OR6, NR7R8, NR8COR10, NR8SO2R10 or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NR7R8; R4 is NR8CONR8R9, NR8COR9, NR8SO2R9, or W-CONR8R9, where W is a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; and R5 is Formula (A) methods for their synthesis, pharmaceutical compositions comprising them and their use in medicine, in particular for the treatment of cancer.

Phenyl-substituted alkenylcarboguanidides carrying perfluoroalkyl groups, a process for their preparation, their use as a medicament or diagnostic agent, and also a medicament containing them

Phenyl-substituted alkenylcarboguanidides carrying perfluoroalkyl groups, a process for their preparation, their use as a medicament or diagnostic agent, and also a medicament containing them. Phenyl-substituted alkenylcarboguanidides carrying perfluoroalkyl groups, of the formula I in which the substituents have the meanings stated in the description, and their pharmaceutically suitable salts, are described. They are obtained by reacting a compound II with guanidine, in which R(1) to R(5) and R(A), R(B), R(C) and R(D) have the stated meaning, and L is a leaving group which easily undergoes nucleophilic substitution. Compounds I are excellent cardiovascular therapeutic agents.