28821-18-3

Usage

Uses

Used in Pharmaceutical Applications:
7-(ethylamino)-4-methyl-2-benzopyrone is used as a therapeutic agent for its potential health benefits in treating various diseases, such as cancer and neurodegenerative disorders. Its antioxidant and anti-inflammatory properties contribute to its potential as a promising pharmaceutical candidate.
Used in Skincare Industry:
In the skincare industry, 7-(ethylamino)-4-methyl-2-benzopyrone is used as an ingredient in sunscreens due to its ability to absorb UV radiation, providing protection against harmful ultraviolet rays and reducing the risk of skin damage and premature aging.
Used in Antimicrobial Applications:
7-(ethylamino)-4-methyl-2-benzopyrone is used as an antimicrobial agent against certain strains of bacteria and fungi, making it a potential candidate for use in various antimicrobial products, such as creams, ointments, and disinfectants.
Used in Cosmetic Industry:
In the cosmetic industry, 7-(ethylamino)-4-methyl-2-benzopyrone is used as an ingredient in various cosmetic products, such as creams, lotions, and serums, due to its potential antioxidant and anti-inflammatory properties, which can contribute to skin health and appearance.

InChI:InChI=1/C12H13NO2/c1-3-13-9-4-5-10-8(2)6-12(14)15-11(10)7-9/h4-7,13H,3H2,1-2H3

Upstream product

• 91-44-1 7-diethylamino-4-methylcoumarin 
• 26093-31-2 7-amino-4-methylcoumarin. 
• 621-31-8 3-(ethylamino)phenol 
• 141-97-9 ethyl acetoacetate 
• 75-03-6 ethyl iodide 
• 7159-96-8 ethyl N-(3-hydroxyphenyl)carbamate 
• 591-27-5 m-Hydroxyaniline 
• 101973-09-5 7-[N-(p-toluenesulfonyl)amino]-4-methylcoumarin 
• 58632-48-7 (4-methyl-2-oxo-2H-1-benzopyran-7-yl)carbamic acid ethyl ester 
• 1346523-56-5 7-[ethyl-(4-methanesulfonylphenyl)amino]-4-methylcoumarin 

Downstream Products

• 1264299-02-6 C₂₀H₂₀BrNO₃ 
• 1264299-01-5 C₁₉H₁₈BrNO₂ 
• 1346523-59-8 4-{[ethyl-(4-methylcoumarin-7-yl)amino]methyl}benzoic acid methyl ester 
• 1346523-61-2 4-{[ethyl-(4-methylcoumarin-7-yl)amino]methyl}benzoic acid 
• 1441046-64-5 4-(7-(ethylamino)-4-methyl-2-oxo-2H-chromen-3-yl)-benzaldehyde 
• 1017606-29-9 C₁₉H₁₆INO₃ 

Relevant academic research and scientific papers

Discovery of Potent Coumarin-Based Kinetic Stabilizers of Amyloidogenic Immunoglobulin Light Chains Using Structure-Based Design

In immunoglobulin light-chain (LC) amyloidosis, transient unfolding or unfolding and proteolysis enable aggregation of LC proteins, causing potentially fatal organ damage. A drug that kinetically stabilizes LCs could suppress aggregation; however, LC sequences are variable and have no natural ligands, hindering drug development efforts. We previously identified high-throughput screening hits that bind to a site at the interface between the two variable domains of the LC homodimer. We hypothesized that extending the stabilizers beyond this initially characterized binding site would improve affinity. Here, using protease sensitivity assays, we identified stabilizers that can be divided into four substructures. Some stabilizers exhibit nanomolar EC50 values, a 3000-fold enhancement over the screening hits. Crystal structures reveal a key π-πstacking interaction with a conserved tyrosine residue that was not utilized by the screening hits. These data provide a foundation for developing LC stabilizers with improved binding selectivity and enhanced physicochemical properties.

Discovery of coumarin-based selective aldehyde dehydrogenase 1A1 inhibitors with glucose metabolism improving activity

Overexpression of aldehyde dehydrogenase 1A1 (ALDH1A1) is associated with the occurrence and development of obesity and insulin resistance. Herein, a series of coumarin-based ALDH1A1 inhibitors were designed, synthesized and evaluated. Among them, compounds 10, 14 and 26 exhibited potent inhibitory activity against ALDH1A1 and high selectivity over ALDH1A2, ALDH1A3, ALDH2 and ALDH3A1. Optimized compound 10 showed markedly improved pharmacokinetic characters and ADME profiles comparing to the lead compound 1. In vitro study demonstrated that 10 alleviated palmitic acid-induced impairment of glucose consumption in HepG2 cells.

BENZOPYRANE AND IMIDAZOLE DERIVATIVES USEFUL FOR THE STABILIZATION OF AMYLOIDOGENIC IMMUNOGLOBULIN LIGHT CHAINS

In immunoglobulin light chain amyloidosis (AL), the unique antibody light chain (LC) protein that is secreted by monoclonal plasma cells in each patient misfolds and/or aggregates, a process leading to organ degeneration. For treating AL patients, such as those with substantial cardiac involvement who have difficulty tolerating existing chemotherapy regimens, provided herein are small molecule compounds of Formula Ia, Formula Ib, and Formula II that are kinetic stabilizers of the native dimeric structure of full-length LCs, which compounds can slow or stop the amyloidogenicity cascade at its origin.

Acrylamide-Coumarin-Benzaldehyde as a Turn-on Fluorescent Probe Providing an Enhanced Water Solubility for Detection of Cysteine and Homocysteine

We presented an acrylamide conjugated coumarin (1) as a fluorescent probe for detection of cysteine (Cys) and homocysteine (Hcy). Probe 1 is composed of coumarin as a fluorophore, acrylamide as a reactive site to Cys/Hcy, and benzaldehyde for improvement of the water solubility. To Cys/Hcy, the acrylamide group of 1 readily undergoes Michael addition resulting in a strong fluorescence at 420 nm through an inhibition of photo-induced electron transfer (PET). The turn-on fluorescence change of 1 was observed for Cys and Hcy, but not seen for other biologically abundant thiols (e.g., glutathione, H2S), reactive oxygen and nitrogen species, anions, and metal ions. Moreover, 1 can give strong fluorescence upon the addition of Cys and Hcy in wide pH range and their limits of detection for Cys and Hcy turned out to be 17.25 and 8.69 μM, respectively.

7-substituted amino-4-methylcoumarin derivative, as well as preparation method and medical application thereof

The invention belongs to the field of medicinal chemistry, and relates to a 7-substituted amino-4-methylcoumarin derivative, as well as a preparation method and application of the 7-substituted amino-4-methylcoumarin derivative as a therapeutic agent in the medical aspect, especially as an ALDH1A1 inhibitor in the aspects of reducing blood glucose and the like.

Coumarin-based turn-on fluorescence probes for highly selective detection of Pi in cell culture and Caenorhabditis elegans

Abstract Two coumarin-based fluorescence probes, 1 and 2, containing a methoxy oxalyl group as a reaction site were developed. These two novel probes displayed an instant turn-on fluorescence response specific towards Pi without interference from ATP and PPi. A selective 23-fold increase in fluorescence for 1 (in DMSO-HEPES) and a 20-fold increase for 2 (in DMSO) were observed. The proposed sensing mechanism for these compounds is Pi-triggered acetamide bond cleavage leading to release of the blue fluorophore coumarin, which was supported by 1H NMR and mass spectrometry data. Probe 1 was successfully used to image endogenous and exogenous Pi in living cells and to trace Pi released from ATP by apyrase in Caenorhabditis elegans.

BODIPY-Coumarin Conjugate as an Endoplasmic Reticulum Membrane Fluidity Sensor and Its Application to ER Stress Models

An endoplasmic reticulum (ER) membrane-selective chemosensor composed of BODIPY and coumarin moieties and a long alkyl chain (n-C18) was synthesized. The emission ratio of BODIPY to coumarin depends on the solution viscosity. The probe is localized to the ER membrane and was applied to reveal the reduced ER membrane fluidity under ER stress conditions.

A self-calibrating bipartite viscosity sensor for mitochondria

A self-calibrating bipartite viscosity sensor 1 for cellular mitochondria, composed of coumarin and boron-dipyrromethene (BODIPY) with a rigid phenyl spacer and a mitochondria-targeting unit, was synthesized. The sensor showed a direct linear relationship between the fluorescence intensity ratio of BODIPY to coumarin or the fluorescence lifetime ratio and the media viscosity, which allowed us to determine the average mitochondrial viscosity in living HeLa cells as ca. 62 cP (cp). Upon treatment with an ionophore, monensin, or nystatin, the mitochondrial viscosity was observed to increase to ca. 110 cP.

Non-conjugated dendrimers with a porphyrin core and coumarin chromophores as peripheral units: Synthesis and photophysical properties

Three porphyrin-cored dendrimers with non-conjugated coumarins as dendrons have been synthesized and characterized. The photophysical properties of the title compounds were investigated by means of UV/Vis absorption and fluorescence spectroscopy in dilute CH2Cl2 solutions and in thin neat films. The intramolecular energy transfer from the coumarin units to the porphyrin core clearly reveals two factors influencing energy-transfer efficiency. Firstly, a better spectral overlap between the absorption spectrum of porphyrin core and the emission spectrum of the coumarin moiety results in high energy-transfer efficiency. Secondly, a long alkyl side-chain improves solubility of dendrimers, but also prevents the coumarins from self-quenching. Hence, the dendrimer with N-octyl groups possesses a higher efficiency than that with N-ethyl groups. The dendrimers emit red light with higher fluorescence quantum yields over the free porphyrin.

Anticancer drug release from a mesoporous silica based nanophotocage regulated by either a one- or two-photon process

An excellent mesoporous silica nanoparticle (MSN) based drug deliver system (DDS) was reported for regulated anticancer drug release upon the irradiation of either one- or two-photon excitation. In this system, the coumarin grafted on MSN acted as both the "phototrigger" for the drug release and fluorescence group for cell luminescence imaging. External light manipulations such as changing irradiation wavelength, intensity, and time can regulate the release of the anticancer drug precisely. Biological studies in vitro suggest that the drug carrier can effectively deliver the anticancer drug into intracellular environs and, hence, promote the drug action to kill the cancer cells upon irradiation. We envision that the good biocompatibility, cellar uptake property, and efficient photoregulated drug release will be of great benefit to future controlled release in vivo biomedical applications.