14736-31-3

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 4-oxo-4H-1-benzopyran-2-carboxylate is used as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Product Synthesis:
ethyl 4-oxo-4H-1-benzopyran-2-carboxylate serves as a key component in the production of a range of chemical products, highlighting its versatility in different chemical processes.
Used in Research Laboratories:
Ethyl 4-oxo-4H-1-benzopyran-2-carboxylate is employed as a reagent in research settings, particularly in drug discovery and organic synthesis, where it aids in the exploration of new chemical pathways and the creation of novel molecules.
Used in Drug Discovery:
In the field of drug discovery, ethyl 4-oxo-4H-1-benzopyran-2-carboxylate is utilized as a starting material or a building block for the design and synthesis of potential drug candidates, playing a crucial role in advancing pharmaceutical research.

InChI:InChI=1/C12H10O4/c1-2-15-12(14)11-7-9(13)8-5-3-4-6-10(8)16-11/h3-7H,2H2,1H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 95-92-1 oxalic acid diethyl ester 
• 65950-31-4 ethyl 2-hydroxy-4-oxochroman-2-carboxylate 
• 64-17-5 ethanol 
• 23866-72-0 ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate 
• 7250-94-4 o-acetoxyacetophenone 
• 60-29-7 diethyl ether 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 4940-39-0 acide chromone carboxylique-2 
• 4940-37-8 ethyl 4-(2-hydroxyphenyl)-2,4-dioxobutanoate 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 108-95-2 phenol 
• 5112-47-0 4-oxo-4H-chromene-2-carbonyl chloride 

Downstream Products

• 30982-57-1 1-[4-(2-hydroxy-phenyl)-4-oxo-2-piperidino-crotonoyl]-piperidine 
• 53603-56-8 N-(pyridin-2-yl)-4-oxo-4H-chromene-2-carboxamide 
• 93949-13-4 Chromon-carbonsaeure-(2)-di-butylamid 
• 97020-83-2 4-(2-hydroxy-phenyl)-2-isopropylamino-4-oxo-crotonic acid isopropylamide 
• 32773-96-9 N,N-diethyl-4-oxo-4H-chromene-2-carboxamide 
• 38322-77-9 4-thioxo-4H-chromene-2-carboxylic acid ethyl ester 
• 36817-92-2 5-(2-hydroxy-phenyl)-1⁽²⁾H-pyrazole-3-carboxylic acid hydrazide 
• 90915-59-6 2-amino-4-(2-hydroxy-phenyl)-4-oxo-crotonic acid amide 
• 87930-46-9 N-<3-(2-hydroxybenzoyl)-2-pyrrolidin-1-ylacryloyl>pyrrolidine 
• 121727-08-0 2-(2-hydroxybenzoyl)methinyl-3-oxo-6,7-dimethyl-1,2,3,4-tetrahydroquinoxaline 
• 121727-07-9 2-(2-hydroxybenzoyl)methinyl-3-oxo-1,2,3,4-tetrahydroquinoxaline 
• 30095-79-5 ethyl 6-nitro-4-oxo-4H-chromene-2-carboxylate 
• 24698-77-9 ethyl Chroman-2-carboxylate 
• 4940-39-0 acide chromone carboxylique-2 

Relevant academic research and scientific papers

Chromone derivatives which bind to human hair

Chromone derivatives bearing a quaternary ammonium functionality which bind to human hair were synthesised. The radical scavenging activity, according to the DPPH assay, of the chromone derivatives is considerably lower compared with flavonoids. The compounds show interesting UV absorption properties that depend on the position of a methoxy substituent. A bathochromic shift of 29 nm was observed when the methoxy group on the ammonium salts were shifted from position 7 to position 6.

Biomimetic type approach to the tricyclic core of xyloketals. Application to a short, stereocontrolled synthesis of alboatrin and first synthesis of xyloketal G

A convenient approach to the linear tetrahydrofurano benzopyran ring system of xyloketals is described. An orthoester Claisen rearrangement of a chromenol and an intra-molecular cationic cyclization are the key steps in the synthesis. A short, stereocontrolled and high yield synthesis of the phytotoxic metabolite alboatrin was achieved employing this strategy. A unique case of Lewis acid catalyzed isomerization of epi-alboatrin to alboatrin was observed. Subsequently this methodology was extended for the first total synthesis of xyloketal G, where a one pot reaction of three steps viz., acetylation, isomerization and demethylation occurred during acetylation of a mixture of nor-o-methyl xyloketal G and nor-o-methyl epi xyloketal G in presence of AlCl3 to furnish xyloketal G in very good overall yield.

Design, synthesis, and inhibitory activity of potent, photoswitchable mast cell activation inhibitors

Allergic reactions affect millions of people worldwide. The need for new and effective antiallergic agents is evident, and insight into the underlying mechanisms that lead to allergic events is necessary. Herein, we report the design, synthesis, and activity of photoswitchable mast cell activation inhibitors. In mast cell degranulation assays, these inhibitors possess significantly greater potency than an original, chromone-based antiallergic agent. Furthermore, one of the photoswitchable inhibitors shows a significant difference in inhibitory activity between its two photoisomeric forms. Further optimization could ultimately lead to a photoswitchable compound suitable for studying mechanisms involved in allergic reactions in a novel manner, with activity addressable by light and with precise spatiotemporal control over events at the molecular level.

A novel synthesis of chromone based unnatural α -amino acid derivatives

An efficient method for the preparation of chromone based α -amino acid derivatives by alkylation of glycinate schiff base with 3-bromomethyl chromone as well as 2-bromomethyl chromone has been described. Using this method, 2-amino-3-(4-oxo-2-chromenyl)propanoic acid and 2-amino-3-(4-oxo-3-chromenyl)propanoic acid, two novel chromone-amino acid conjugates have been prepared. Furthermore, the separation of chromone amino acid enantiomers by chiral column chromatography was accomplished. Graphical Abstract?: Synopsis: An efficient method for the preparation of chromone based α -amino acid derivatives by alkylation of glycinate schiff base with 3-bromomethyl chromone as well as 2-bromomethyl chromone has been described. These conjugates can be considered as analogues of phenyl alanine where phenyl group has been replaced by chromone moiety.[Figure not available: see fulltext.].

An efficient construction of 4-OXO-4H-chromene-2-carboxylate derivatives via one-pot cascade reaction under solvent-free conditions

An efficient synthetic strategy to chromone derivatives from commercially available diethyl acetylenedicarboxylate and phenols via a one-pot cascade reaction has been developed. Performing the reaction using pyridine and polyphosphoric acid as the catalyst at room temperature and 90°C without any solvent gave the chromone derivatives in good to high yields at one time. A possible reaction pathway was also proposed and supported by the experiment. This protocol is environmentally friendly and metal-free, with advantages including short reaction times, convenient operation, and mild reaction conditions.

Combining QSAR classification models for predictive modeling of human monoamine oxidase inhibitors

Due to their role in the metabolism of monoamine neurotransmitters, MAO-A and MAO-B present a significant pharmacological interest. For instance the inhibitors of human MAO-B are considered useful tools for the treatment of Parkinson Disease. Therefore, the rational design and synthesis of new MAOs inhibitors is considered of great importance for the development of new and more effective treatments of Parkinson Disease. In this work, Quantitative Structure Activity Relationships (QSAR) has been developed to predict the human MAO inhibitory activity and selectivity. The first step was the selection of a suitable dataset of heterocyclic compounds that include chromones, coumarins, chalcones, thiazolylhydrazones, etc. These compounds were previously synthesized in one of our laboratories, or elsewhere, and their activities measured by the same assays and for the same laboratory staff. Applying linear discriminant analysis to data derived from a variety of molecular representations and feature selection algorithms, reliable QSAR models were built which could be used to predict for test compounds the inhibitory activity and selectivity toward human MAO. This work also showed how several QSAR models can be combined to make better predictions. The final models exhibit significant statistics, interpretability, as well as displaying predictive power on an external validation set made up of chromone derivatives with unknown activity (that are being reported here for first time) synthesized by our group, and coumarins recently reported in the literature.

Synthesis and evaluation of chromone-2-carboxamido-alkylamines as potent acetylcholinesterase inhibitors

Alzheimer’s disease (AD) is considered one of the greatest global public burdens. Pathophysiology of AD is proposed to be associated with reduced levels of the neurotransmitter acetylcholine (ACh). Cholinesterase enzymes, namely acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) cleave ACh via hydrolysis. Cholinesterase inhibitors (ChEIs) are the main group of drugs currently used for the treatment of AD. Novel chromone-2-carboxamido-alkylamines (7–18) were designed, synthesized, and evaluated for cholinesterase inhibitory activity. The compounds exhibited potent AChE inhibitory activities at micromolar range (IC50 0.09–9.16 μM) and demonstrated weak BChE inhibitory activities (IC50 12.09–44.56 μM). Compound 14 (IC50 0.09 ± 0.02 μM) was the most potent AChEI in this series; it showed higher activity than the clinical used drug tacrine. Enzyme kinetic study suggested that 14 was an uncompetitive inhibitor. Molecular docking study revealed that 14 was a dual-binding site inhibitor. Compound 14 did not induce any concentration-related cytotoxic effect against SH-SY5Y cells. It also showed neuroprotective effect in the cell line. Chromone-2-carboxamido-alkylamines can be promising lead compounds for development of anti-Alzheimer’s agents.

Exclusive photodimerization reactions of chromone-2-carboxylic esters depending on reaction media

The irradiation of chromone-2-carboxylic esters resulted in the stereo- and regioselective formation of C2 chiral anti-HH dimers from the triplet excited state. On the contrary, photolysis in the solid-state gave anti-HT dimers exclusively controlled by molecular arrangement in the crystal.

Discovery of novel chromone derivatives containing a sulfonamide moiety as potential anti-TSWV agents

A number of chromone derivatives containing sulfonamide structure were designed and synthesized. Firstly, the target compounds were evaluated for anti-TSWV activities in vivo by the half-leaf method. We found that most of the compounds had good anti-TSWV activities. Among them, compound 12B had excellent anti-TSWV inactivating activity with an EC50 of 80.5 μg/mL, which was significantly better than xiangcaoliusuobingmi (765.7 μg/mL). Secondly, TSWV nucleocapsid protein (N) was expressed and purified, and the affinity between the compounds and TSWV N was tested by microscale thermophoresis (MST). Compound 12B had a good affinity for TSWV N with a Kd value of 5.02 μM, which was superior to xiangcaoliusuobingmi (29.83 μM). Finally, in order to study the mode of interaction between the compound 12B and TSWV N, we carried out molecular docking. The results indicated that compound 12B might inactivate the virus by destroying the TSWV N oligomer structure. These results lay a solid foundation for the further discovery of chromone derivatives containing sulfonamide structure with high anti-TSWV activities.

Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions

The stereocontrolled construction of biologically relevant chromanones and tetrahydroxanthones has been achieved through the addition of alkynes to benzopyrylium trilfates under the influence of copper bis(oxazoline) catalysis. Excellent levels of enantiocontrol (63–98 % ee) are achieved in the addition of a variety of alkynes to an array of chromenones with a hydrogen in the 2-position. Promising levels of enantiocontrol (54–67 % ee) are achieved in the alkynylation of chromenones with esters in the 2-position, generating tertiary ether stereocenters resembling those frequently found in naturally occurring metabolites.