23568-85-6

Usage

Uses

Used in Pharmaceutical Industry:
3'-CYANO-2,2,2-TRIFLUOROACETOPHENONE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block in the development of new drugs with potential therapeutic applications.
Used in Biochemical Research:
In the field of biochemistry, 3'-CYANO-2,2,2-TRIFLUOROACETOPHENONE serves as a useful reagent in the preparation of 3,5-disubstituted and 1,3,5-trisubstituted benzamides. These benzamides have potential reversible inhibitory functions against HRV protease 3C, an enzyme involved in viral replication. By inhibiting this enzyme, the compound may contribute to the development of antiviral drugs.
Used in Chemical Synthesis:
3'-CYANO-2,2,2-TRIFLUOROACETOPHENONE is also utilized as a key intermediate in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemistry, and other specialized fields. Its unique combination of functional groups makes it a valuable component in the development of novel molecules with specific properties and applications.

InChI:InChI=1/C9H4F3NO/c10-9(11,12)8(14)7-3-1-2-6(4-7)5-13/h1-4H

Upstream product

• 13531-48-1 methyl 3-cyanobenzoate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 807329-97-1 TurboGrignard 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 69113-59-3 3-iodobenzonitrile 

Downstream Products

• 35462-62-5 3-(2,2,2-Trifluoro-1-trifluoromethyl-ethyl)-benzonitrile 
• 1021874-08-7 3-(trifluoroacetyl)benzamide 

Relevant academic research and scientific papers

One-Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α-Aryl-α-Trifluoromethyl Alcohols

A novel straightforward one-pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α-aryl-α-trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2-trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one-pot process: the iPrMgCl·LiCl-mediated iodine/magnesium-exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2-trifluoroethyl trifluoroacetate; and the reduction of in-situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α-aryl or α-heteroaryl-α-trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.

New anti-viral drugs for the treatment of the common cold

Human Rhinovirus (HRV) is the most important aetiologic agent of common cold in adults and children. HRV is a single-stranded, positive sense RNA virus and, despite the high level of conservation among different serotypes, sequence alignment of viral protease 3C with mammalian protease reveals no homology. Thus, protease 3C is an optimal target for the development of anti-HRV agents. In the present work we investigated the design, the synthesis and the development of new potential reversible inhibitors against HRV protease 3C. Docking studies on the crystallized structure of HRV2 protease 3C led us to the design and the synthesis of a series of 3,5 disubstituted benzamides able to act as analogues of the substrate. We also developed 1,3,5 trisubstituted benzamides where aromatic substitutions on the aryl ring led us to investigate the importance of π-π interaction on the stabilization of protease 3C-inhibitor complex. All structures were tested for enzymatic inhibition on HRV14 protease 3C. Results highlighted the inhibitory activity of compounds 13, 14, and 20 (91%, 81%, and 85% at 10 μM, respectively), with the latter exhibiting an ID50 (dose that inhibits 50% of the viral cytopathic effect) on HRV-14 = 25 μg/ml.