59507-94-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-4H-chromen-4-one is used as a pharmaceutical agent for its anti-tumor, anti-inflammatory, and anti-bacterial properties. It has been studied for its potential in the development of therapeutic agents for treating various diseases and conditions.
Used in Drug Development:
3-Amino-4H-chromen-4-one derivatives are used in drug development for their potential in treating various diseases and conditions. The unique structure and properties of 3-amino-4H-chromen-4-one make it a promising candidate for the development of new therapeutic agents.
Used in Research:
3-Amino-4H-chromen-4-one is used in research for its potential pharmaceutical and biological activities. It is being studied for its anti-tumor, anti-inflammatory, and anti-bacterial properties, as well as its potential applications in the development of therapeutic agents for various diseases and conditions.

Upstream product

• 59507-92-5 3-nitro-4H-chromen-4-one 
• 120869-41-2 1a,7a-Dihydro-1H-2-oxa-1-aza-cyclopropa[b]naphthalen-7-one 
• 155060-17-6 3-Azido-4-chromanone 
• 125418-83-9 2-(2-formylphenoxy)acetonitrile 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 1776-09-6 3-bromochroman-4-one 
• 90-02-8 salicylaldehyde 
• 106129-86-6 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 
• 1084-62-4 1-(2-hydroxy-phenyl)-3-piperidin-1-yl-propenone 
• 14386-72-2 1-(2'-hydroxyphenyl)-3-phenylmethylamino-2-propen-1-one 

Downstream Products

• 6928-56-9 3-aminoflavone 
• 67139-35-9 3-amino-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 
• 67139-36-0 3-amino-2-(4-chlorophenyl)-4H-1-benzopyran-4-one 
• 92831-09-9 3-amino-2-(4-bromophenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Photoredox-Catalyzed Cascade of o-Hydroxyarylenaminones to Access 3-Aminated Chromones

Reported herein is a photoredox-catalyzed amination of o-hydroxyarylenaminones with tert-butyl ((perfluoropyridin-4-yl)oxy)carbamate, a versatile amidyl-radical precursor developed in our laboratory. This work establishes a new cascade pathway for the ass

NHC-catalyzed green synthesis of functionalized chromones: DFT mechanistic insights and: In vitro activities in cancer cells

An efficient synthesis of 3-aminochromones and 3-alkylchromones by a N-heterocyclic carbene (NHC) catalyzed intramolecular hydroacylation reaction of corresponding salicylaldehyde derived nitriles and activated alkynes respectively in ionic liquids under microwave conditions is reported. This protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, and convenient operation using the commercially available thiazolium catalyst. The origin of the chemical reactivity of the NHC-catalyzed intramolecular hydroacylation reaction of nitriles is studied using Density Functional Theory (DFT). The results suggest that 3-aminochromone formation occurs via an acyl anion intermediate called a Breslow intermediate (INT2) through TS2. The Breslow intermediate (INT2) forms a carbon-carbon bond with the nitrile carbon to produce an imine intermediate INT3viaTS3, which further undergoes imine to amine tautomerism to give the end product. Some of the derivatives of 3-aminochromone are subjected to amine functionalization in one pot to obtain a library of compounds for anticancer activity. Among the investigated compounds, 2c (SVM-2), 4c (SVM-4) and 2d (SVM-9) show IC50 values of 5.18, 4.89 and 27.3 μM respectively in HeLa S3 cancer cells. Compound 5c (SVM-5) shows IC50 values of 13.3 and 14.2 μM in A549 and HeLa S3 cancer cells, respectively. Compounds 2c (SVM-2) and 4c (SVM-4) produce morphological changes and control the colony formation in HeLa S3 cells, which indicates that these small molecules are potential candidates for anticancer drugs.

MGLUR7 AGONIST COMPOUNDS FOR TREATING MGLUR7- REGULATED DISEASES, DISORDERS, OR CONDITIONS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof wherein Z, R1, R2, R3, R4, R5 and R6 are as defined in the specification, a process for

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.

N-heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: An easy access to 3-aminochromones

(Figure presented) An immense effort has been made to develop an efficient strategy for the carbon-carbon bond formation between aldehyde and nitrile intramolecularly using an N-heterocyclic carbene catalyst to derive 3-aminochromone derivatives In good to excellent yields (80-95%).

Radical chain reactions of α-azido ketones with tributyltin hydride: Reduction vs nitrogen insertion and 1,2-hydrogen shift in the intermediate N-stannylaminyl radicals

The radical chain reactions of a variety of acyclic and cyclic α-azido ketones with tributyltin hydride have been investigated. The derived N-(tributylstannyl)aminyl radicals normally undergo H-abstraction reaction yielding corresponding amines, and thence symmetrical pyrazines by subsequent self-condensation, in competition with 1,2-H-migration from the α-carbon to nitrogen leading to α-imino ketone decomposition products with loss of the chain-carrying tributyltin radical. The noteworthy occurrence of a quite uncommon radical 1,2-hydrogen-atom shift is considered to be largely due to consequent formation of a highly stable, captodative carbon-centred radical. In contrast with our previous N-stannylaminyl radicals produced from α-azido-β-keto esters, the present aminyl congeners give poor amounts (or even none) of nitrogen-inserted amides/lactams, which are envisaged to arise from intramolecular three-membered cyclisation onto the ketone moiety followed by β-scission of the resultant alkoxyl radical. It is inferred that adequate stabilisation of the eventual ring-opened carbon radical be a major factor for the successful outcome of the regiospecific nitrogen insertion process. Evidence is also presented that chemoselective attack of tris(trimethylsilyl)silyl radical to the ketone oxygen of an α-azido ketone gives rise to deazidation as a likely consequence of β-elimination of azidyl radical by the ensuing α-silyloxyalkyl radical. X-Ray crystal structure analyses of the bromo ketone 5a, the azido ketone 5b, the caprolactam 22, and the pyrazine 26 have been performed.

Base-promoted reactions of α-azido ketones with aldehydes and ketones: A novel entry to α-azido-β-hydroxy ketones and 2,5-dihydro-5-hydroxyoxazoles

The base-promoted reaction of α-azido ketones with aldehydes and ketones provides a new and simple route to either α-azido-β-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The α-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the α-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the α-azido ketone enolate.

The Reaction of S,S-Diphenylsulphilimine with Benzopyran-4-ones and Benzopyran-4-thiones

Benzopyran-4-ones unsubstituted at carbons 2 and 3 yield aziridines, amines and isoxazoles on treatment with diphenylsulphilimine.The product composition is temperature dependent, aziridines being the major products at room temperature and amines at highe

Synthesis of 4,10-Dihydro-4,10-dioxo-1H--benzopyranopyridine, 4,5-Dihydro-4,5-dioxo-1H--benzopyranopyridine and 1,5-Dihydro-1,5-dioxo-4H--benzopyranopyridine derivatives from Aminobenzopyrones

3-Aminochromone and 3-aminocoumarin were condensed with diethyl ethoxymethylenemalonate and with dimethyl acetylenedicarboxylate to give intermediates, which were thermally cyclized to give 4,10-dihydro-4,10-dioxo-1H--benzopyranopyridinecarboxylates and 1,5-dihydro-1,5-dioxo-4H--benzopyranopyridinecarboxylates. 2-Aminochromone was converted to 4,5-dihydro-4,5-dioxo-1H--benzopyranopyridinecarboxylate via an intermediate condensation product with diethyl ethoxymethylenemalonate.These esters were hydrolyzed to the corresponding carboxylic acids (21, 30, 36, 50, and 60).Attempts to prepare 4,5-dihydro-4,5-dioxo-1H--benzopyranopyridinecarboxylates from 4-aminocoumarin were unsuccessful.