64481-25-0

Usage

InChI:InChI=1/C12H7FO4/c13-8-2-3-10-9(5-8)12(16)7(6-17-10)1-4-11(14)15/h1-6H,(H,14,15)/b4-1+

Upstream product

• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 405-51-6 4-fluorophenyl acetate 
• 69155-76-6 6-fluorochromone-3-carboxaldehyde 
• 141-82-2 malonic acid 
• 371-41-5 4-Fluorophenol 

Relevant academic research and scientific papers

Discovery of Novel Chromone Derivatives Containing a Sulfonamide Moiety as Anti-ToCV Agents through the Tomato Chlorosis Virus Coat Protein-Oriented Screening Method

A number of novel chromone derivatives containing sulfonamide moieties were designed and synthesized, and the activity of compounds against tomato chlorosis virus (ToCV) was assessed using the ToCVCP-oriented screening method. Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were established based on the dissociation constant (Kd) values of the target compounds, and compound 35 was designed and synthesized with the aid of CoMFA and CoMSIA models. The study of affinity interaction indicated that compound 35 exhibited excellent affinity with ToCVCP with a Kd value of 0.11 μM, which was better than that of the positive control agents xiangcaoliusuobingmi (0.44 μM) and ningnanmycin (0.79 μM). In addition, the in vivo inhibitory effect of compound 35 on the ToCVCP gene was evaluated by the quantitative real-time polymerase chain reaction. ToCVCP gene expression levels of the compound 35 treatment group were reduced by 67.2%, which was better than that of the positive control agent ningnanmycin (59.5%). Therefore, compound 35 can be used as a potential anti-ToCV drug in the future.

Discovery and Optimization of Chromone Derivatives as Novel Selective Phosphodiesterase 10 Inhibitors

Phosphodiesterase 10 (PDE10) inhibitors have received much attention as promising therapeutic agents for central nervous system (CNS) disorders such as schizophrenia and Huntington's disease. Recently, a hit compound 1 with a novel chromone scaffold has shown moderate inhibitory activity against PDE10A (IC50 = 500 nM). Hit-to-lead optimization has resulted in compound 3e with an improved inhibitory activity (IC50 = 6.5 nM), remarkable selectivity (>95-fold over other PDEs), and good metabolic stability (RLM t1/2 = 105 min) by using an integrated strategy (molecular modeling, chemical synthesis, bioassay, and cocrystal structure). The cocrystal structural information provides insights into the binding pattern of 3e in the PDE10A catalytic domain to highlight the key role of the halogen and hydrogen bonds toward Tyr524 and Tyr693, respectively, thereby resulting in high selectivity against other PDEs. These new observations are of benefit for the rational design of the next generation PDE10 inhibitors for CNS disorders.

Synthesis of Chromone-Containing Allylmorpholines through a Morita–Baylis–Hillman-Type Reaction

The first example of an unusual addition of chromone-substituted acrylic acid to enamines is described. The process shows high versatility concerning both enamines and chromones. The reaction is catalyzed by tertiary amines and is highly likely of Morita–

Synthesis and characterization of new N-alkylated pyridin-2(1H)-ones

A series of novel N-substituted pyridin-2(1H)-one derivatives have been synthesized by reacting (E)-ethyl 3-(6-fluoro-4-oxo-4H-chromen-3-yl)acrylate, with various alkylamines, benzylamines, diaminoalkanes, propargyl amine, 2-amino-1,3-dihydroxypropane, etc. under basic conditions, in 60-83% yield. The structures of the compounds have been established on the basis of their physical and spectral characterization data (1H and 13C NMR, UV-Vis, FT-IR, and HRMS) and further confirmed by X-ray crystallographic analysis of a representative compound. Antibacterial activity of obtained 2-pyridones have been investigated against three human pathogen bacterial strains. Most of the compounds exhibit low activity as compared to the reference.