1053228-81-1

Basic information

• Product Name: N-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-carboxamide
• Synonyms: N-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-carboxamide
• CAS NO: 1053228-81-1
• Molecular Weight: 281.268
• Mol File: 1053228-81-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-carboxamide(1053228-81-1)
• EPA Substance Registry System: N-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-carboxamide(1053228-81-1)

Safety Data

• Hazardous Substances Data: 1053228-81-1(Hazardous Substances Data)

Upstream product

• 39079-62-4 chromone-3-carboxylic acid 
• 123-30-8 4-amino-phenol 

Relevant articles and documents

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.

In search for new chemical entities as adenosine receptor ligands: Development of agents based on benzo-γ-pyrone skeleton

A selected series of chromone carboxamides synthesized in our laboratory were evaluated by radioligand binding studies towards adenosine receptors. All the chromone-3-carboxamides (compounds 8-12) exhibit A2B receptor displacement percentage su

Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors

Two series of novel chromone derivatives were synthesized and investigated for their ability to inhibit the activity of monoamine oxidase. The SAR data indicate that chromone derivatives with substituents in position 3 of γ-pyrone nucleus act preferably a