39079-64-6

Basic information

• Product Name: 4H-1-Benzopyran-3-carboxamide, 4-oxo-N-phenyl-
• CAS NO: 39079-64-6
• Molecular Formula: C16H11NO3
• Molecular Weight: 265.268
• Mol File: 39079-64-6.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-3-carboxamide, 4-oxo-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-3-carboxamide, 4-oxo-N-phenyl-(39079-64-6)
• EPA Substance Registry System: 4H-1-Benzopyran-3-carboxamide, 4-oxo-N-phenyl-(39079-64-6)

Safety Data

• Hazardous Substances Data: 39079-64-6(Hazardous Substances Data)

Upstream product

• 39079-62-4 chromone-3-carboxylic acid 
• 62-53-3 aniline 
• 213273-03-1 4-oxo-2-(N-phenyl)amino-4H-chromene-3-carbaldehyde 
• 39079-63-5 4-oxo-4H-1-benzopyran-3-carbonyl chloride 
• 17422-74-1 3-Formylchromone 
• 118-93-4 o-hydroxyacetophenone 
• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 103-71-9 phenyl isocyanate 

Relevant articles and documents

Synthesis and biological evaluation of chromone-3-carboxamides

The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2-hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, anti-tryponosomal and cytotoxic properties.

Discovery of New Chemical Entities for Old Targets: Insights on the Lead Optimization of Chromone-Based Monoamine Oxidase B (MAO-B) Inhibitors

The discovery of new chemical entities endowed with potent, selective, and reversible monoamine oxidase B inhibitory activity is a clinically relevant subject. Therefore, a small library of chromone derivatives was synthesized and screened toward human monoamine oxidase isoforms (hMAO-A and hMAO-B). The structure-activity relationships studies strengthen the importance of the amide spacer and the direct linkage of carbonyl group to the γ-pyrone ring, along with the presence of meta and para substituents in the exocyclic ring. The most potent MAO-B inhibitors were N-(3′-chlorophenyl)-4-oxo-4H-chromene-3-carboxamide (20) (IC50 = 403 pM) and N-(3′,4′-dimethylphenyl)-4-oxo-4H-chromene-3-carboxamide (27) (IC50 = 669 pM), acting as competitive and noncompetitive reversible inhibitors, respectively. Computational docking studies provided insights into enzyme-inhibitor interactions and a rationale for the observed selectivity and potency. Compound 27 stands out due to its favorable toxicological profile and physicochemical properties, which pointed toward blood-brain barrier permeability, thus being a valid candidate for subsequent animal studies.

COMPOSITIONS AND METHODS FOR TREATING NEUROLOGICAL DISEASES OR INJURY

Provided are compounds for the treatment of neurological diseases or injuries, including neurodegenerative diseases, stroke, trauma, epilepsy, acute and chronic kidney injuries, diabetes mellitus, and/or seizures. In some embodiments, derivatives of vitamin K are provided.