39079-64-6

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 
• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 103-71-9 phenyl isocyanate 
• 17422-74-1 3-Formylchromone 
• 118-93-4 o-hydroxyacetophenone 

Relevant academic research and scientific papers

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.

Synthesis of 3-(N-arylcarbamoyl)chromones from 2-hydroxyarylaminoenones and isocyanates

A new method for the synthesis of 2-unsubstituted and 2-substituted 3-(N-arylcarbamoyl)-chromones by the reaction of 3-dimethylamino-1-(2-hydroxyaryl)prop-2-en-1-ones with arylisocyanates has been proposed.

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.

Discovery of two new classes of potent monoamine oxidase-B inhibitors by tricky chemistry

The discovery of potent and selective monoamine oxidase-B inhibitors for the management of neurodegenerative diseases such as Alzheimer's and Parkinson's diseases is still a challenging endeavor. Herein, we report the discovery of two new classes of poten

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.

Structure-activity relationship study of vitamin K derivatives yields highly potent neuroprotective agents

Historically known for its role in blood coagulation and bone formation, vitamin K (VK) has begun to emerge as an important nutrient for brain function. While VK involvement in the brain has not been fully explored, it is well-known that oxidative stress plays a critical role in neurodegenerative diseases. It was recently reported that VK protects neurons and oligodendrocytes from oxidative injury and rescues Drosophila from mitochondrial defects associated with Parkinson's disease. In this study, we take a chemical approach to define the optimal and minimum pharmacophore responsible for the neuroprotective effects of VK. In doing so, we have developed a series of potent VK analogues with favorable drug characteristics that provide full protection at nanomolar concentrations in a well-defined model of neuronal oxidative stress. Additionally, we have characterized key cellular responses and biomarkers consistent with the compounds' ability to rescue cells from oxidative stress induced cell death.

Discovery of novel A3 adenosine receptor ligands based on chromone scaffold

A project focused on the discovery of new chemical entities (NCEs) as AR ligands that incorporate a benzo-γ-pyrone [(4H)-1-benzopyran-4-one] substructure has been developed. Accordingly, two series of novel chromone carboxamides placed at positions C2 (co

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

An organocatalytic rearrangement of 2-(N-alkyl-/aryl-)amino-4-oxo-4H-1- benzopyran-3-carbaldehyde

2-(Arylamino)-4-oxo-4H-1-benzopyran-3-carbaldehyde rearranges to 4-oxo-4H-1-benzopyran-3-carbanilide when treated with glycine in the presence of formalin, but under similar conditions 2-(alkylamino)-4-oxo-4H-1-benzopyran-3- carbaldehyde rearranges to 3-a

Chromone 3-phenylcarboxamides as potent and selective MAO-B inhibitors

Monoamine oxidase (MAO) is an enzyme, present in mammals in two isoforms MAO-A and MAO-B. These isoforms have a crucial role in neurotransmitters metabolism, representing an attractive drug target in the therapy of neurodegenerative diseases (MAO-B) and d