71682-97-8

Usage

InChI:InChI=1/C9H5F2NO/c10-7-2-1-6(5-8(7)11)9(13)3-4-12/h1-2,5H,3H2

Upstream product

• 76903-88-3 3,4-difluorobenzoyl chloride 
• 75-05-8 acetonitrile 
• 144267-96-9 ethyl 3,4-difluorobenzoate 
• 40706-98-7 3,4-difluorophenacyl bromide 
• 367-11-3 ortho-difluorobenzene 
• 369-33-5 3',4'-difluoroacetophenone 
• 143-33-9 sodium cyanide 

Downstream Products

• 1139743-02-4 2-amino-4-(3,4-difluorophenyl)thiazole-5-carbonitrile 

Relevant academic research and scientific papers

Polysubstituted heterocyclic derivative, preparation method thereof and application of polysubstituted heterocyclic derivative in medicine

The invention provides a polysubstituted heterocyclic derivative, a preparation method thereof and application of the polysubstituted heterocyclic derivative in medicine, and belongs to the technical field of medicinal chemistry. The polysubstituted heterocyclic derivative is a compound shown in a general formula I or II, a pharmaceutically acceptable salt or a solvate of the compound, and the compound can inhibit mRNA demethylase on the protease level and is used for treating diseases related to mRNA demethylase functions.

A Pd-catalyzed asymmetric allylic substitution cascade: Via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans

A Pd-catalyzed asymmetric allylic substitution cascade of allylic meso-dicarbonates with 3-oxo-nitriles has been developed for the synthesis of chiral bicyclic dihydrofurans bearing two vicinal carbon stereocenters. The reaction proceeds via an asymmetric desymmetrization process with the desired products being obtained in high yields and with up to 97% ee. The reaction was performed on a gram-scale and the corresponding bicyclic dihydrofurans could undergo several transformations. The methodology provides an efficient synthetic route to biologically active chiral bicyclic dihydrofurans derivatives.

Discovery and Optimization of Potent, Cell-Active Pyrazole-Based Inhibitors of Lactate Dehydrogenase (LDH)

We report the discovery and medicinal chemistry optimization of a novel series of pyrazole-based inhibitors of human lactate dehydrogenase (LDH). Utilization of a quantitative high-throughput screening paradigm facilitated hit identification, while structure-based design and multiparameter optimization enabled the development of compounds with potent enzymatic and cell-based inhibition of LDH enzymatic activity. Lead compounds such as 63 exhibit low nM inhibition of both LDHA and LDHB, submicromolar inhibition of lactate production, and inhibition of glycolysis in MiaPaCa2 pancreatic cancer and A673 sarcoma cells. Moreover, robust target engagement of LDHA by lead compounds was demonstrated using the cellular thermal shift assay (CETSA), and drug-target residence time was determined via SPR. Analysis of these data suggests that drug-target residence time (off-rate) may be an important attribute to consider for obtaining potent cell-based inhibition of this cancer metabolism target.

Potential antiarthritic agents. II. Benzoylacetonitriles and β-aminocinnamonitriles

Benzoylacetonitrile and β-aminocinnamonitrile are shown to possess potent intiinflammatory activity in the rat adjuvant arthritis model. In a series of phenyl-substituted analogues, only o-, m-, and p-fluorobenzoylacetonitrile and m- and p-fluoro-β-aminocinnamonitrile retained activity. Additionally, β-amino-2- and β-amino-3-thiopheneacrylonitrile and β-oxo-2- and β-oxo-3-thiophenepropionitrile exhibited similar activity. These agents are not believed to be acting via prostaglandin synthetase inhibition. The metabolic profile of benzoylacetonitrile is also described.

Cis-2-benzoyl-3-hydroxy-2-alkenonitriles as anti-inflammatory agents

This disclosure describes new compounds and compositions of matter useful as anti-inflammatory agents and as inhibitors of the progressive joint deterioration characteristic of arthritic disease and the methods of meliorating inflammation and of inhibiting joint deterioration in mammals therewith, the novel active ingredients of said compositions of matter being certain substituted cis-2-benozyl-3-hydroxy-2-alkenonitriles and/or the pharmacologically acceptable cationic salts thereof.