7471-76-3

Basic information

• Product Name: 7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one
• Synonyms: 7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one
• CAS NO: 7471-76-3
• Molecular Formula: C₁₂H₁₁BrO₃
• Molecular Weight: 283.11794
• Mol File: 7471-76-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 415.6°Cat760mmHg
• Flash Point: 205.2°C
• Appearance: /
• Density: 1.499g/cm³
• Vapor Pressure: 4.06E-07mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one(7471-76-3)
• EPA Substance Registry System: 7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one(7471-76-3)

Safety Data

• Hazardous Substances Data: 7471-76-3(Hazardous Substances Data)

Usage

General Description

7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one is a chemical compound with a complex molecular structure. It belongs to the class of organic compounds known as coumarins, which are aromatic compounds containing a benzene ring fused to a 2-pyrone. This particular compound is characterized by the presence of a bromoethoxy group attached to the 7th carbon of the chromen-2-one ring, as well as a methyl group at the 4th carbon. It exhibits potential pharmacological properties and may be used in medicinal chemistry for the development of novel drugs. Additionally, it may also have applications in the field of organic synthesis and chemical research.

InChI:InChI=1/C12H11BrO3/c1-8-6-12(14)16-11-7-9(15-5-4-13)2-3-10(8)11/h2-3,6-7H,4-5H2,1H3

Upstream product

• 107332-83-2 3-(2-bromoethoxy)phenol 
• 141-97-9 ethyl acetoacetate 
• 108-46-3 recorcinol 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 106-93-4 ethylene dibromide 

Downstream Products

• 914772-91-1 7-{2-[4-(4-methoxybenzoyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one 
• 914772-90-0 4-methyl-7-{2-[4-(4-methylbenzoyl)piperazin-1-yl]ethoxy}-2H-chromen-2-one 
• 914772-92-2 7-{2-[4-(2,5-dichlorophenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one 
• 1314133-65-7 7-{2-[4-(3-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one 
• 1314133-64-6 7-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one 
• 914772-87-5 7-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one 
• 914772-88-6 4-methyl-7-{2-[4-(4-methylphenyl)piperazin-1-yl]ethoxy}-2H-chromen-2-one 
• 914772-86-4 4-methyl-7-[2-(4-phenylpiperazin-1-yl)ethoxy]-2H-chromen-2-one 
• 678547-08-5 7-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one 
• 155272-61-0 7-<2-(1-imidazolyl)ethyloxy>-4-methylbenzopyran-2-one 

Relevant articles and documents

Synthesis of uracil–coumarin conjugates as potential inhibitors of virus replication

A series of 1-[(bromophenoxy)alkyl]uracil–coumarin conjugates has been obtained through the preparation of starting 1-[(bromophenoxy)alkyl]uracil derivatives, followed by their treatment with 7-(ω-bromoalkoxy)-4-methyl-2H-chromen-2-ones. Two of the synthesized uracil–coumarin conjugates demonstrated a pronounced inhibitory activity against HCMV and VZV replication in vitro.

Photodegradable coumarin-derived amphiphilic dendrons for DNA binding: Self-assembly and phototriggered disassembly in water and air-water interface

In this article, we demonstrate the self-assembly and photoresponive behavior of a novel coumarin-based amphiphilic dendron in both aqueous solution and air-water interface. The dendritic structure, namely C-IG1, was composed of a lipophilic cholesterol and hydrophilic poly(amido amine) (PAMAM) dendron, and the amphiphilic counterpart is interconnected by a photolabile coumarin carbonate ester, enabling the photoinduced degradation of the amphiphiles in protic solvents via SN1-like mechanism. A Nile red solubilization fluorescence assay suggests a low critical aggregation concentration for the micelle formation of C-IG1 in aqueous solutions (3.9 × 10?5 M); the Langmuir analysis further indicates that C-IG1 possesses significant compressibility in air-water interface, eventually forming homogeneous monolayers with a final molecular area (A0) of 36 ?2. Notably, the micelles and Langmuir monolayer are quite stable until photo-triggered dissociation based on the photocleavage of C-IG1 amphiphile activated by 365-nm incident light. Moreover, the transition in interfacial morphology of the Langmuir monolayer during the assembly and photodegradation processes also can be visually analyzed by incorporating Nile red probes with in situ monitoring through fluorescence microscopy. The thin film deposited on a glass substrate by the Langmuir-Blodgett technique also shows a photoresponsive behavior based on the change in the contact angles of a water droplet on the surface upon light stimulation. The binding affinity of C-IG1 and cyclic DNA determined by the fluorescence quenching analysis of the coumarin reporter suggests a ground-state macromolecular complexation process occurring through polyvalent interactions between the pseudodendrimers and biomacromolecules. The ethidium bromide displacement assay further indicates thus dendriplex formation at low nitrogen-to-phosphorous value (N/P 1) and confirms that the decomplexation accompanied by DNA release can be achieved through an active phototriggered route under spatiotemporal control.

Design, synthesis and biological evaluation of new coumarin-dithiocarbamate hybrids as multifunctional agents for the treatment of Alzheimer's disease

A series of new coumarin-dithiocarbamate hybrids were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's Disease (AD). The biological assays indicated that most of them showed potent inhibition and excellent selectivity towards acetylcholinesterase (AChE), and could inhibit self-induced β-amyloid (Aβ) aggregation. Especially, compound 4n presented the highest ability to inhibit AChE (IC50, 0.027 μM for hAChE) and good inhibition of Aβ aggregation (40.19% at 25 μM). Kinetic and molecular modeling studies revealed that 4n was a mixed-type inhibitor, which could interact simultaneously with the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. In addition, it also possessed specific metal-chelating ability, good BBB permeability and low toxicity on SH-SY5Y neuroblastoma cells. Moreover, compound 4n did not exhibit any acute toxicity in mice at doses up to 1000 mg/kg, and could reverse the cognitive dysfunction of scopolamine-induced AD mice. As far as we know, 4n was the first reported dithiocarbamate derivative with multifunctional activity. Its excellent profiles in vitro and effectivity in vivo highlight this structurally distinct compound as a potential lead compound in the research of innovative multifunctional drugs for AD.

Coumarin derivatives of - dithiocarbamate and synthesis method thereof

The invention discloses a coumarin-dithiocarbamate derivative and a synthesizing method thereof. The synthesizing method of the derivative comprises the following steps: 1) utilizing concentrated sulfuric acid as a catalyst, taking resorcinol and ethyl acetoacetate and putting into a first organic solvent to react to obtain an intermediate 2; 2) taking the intermediate 2 and dibromoalkane, puttinginto a second organic solvent and performing reaction under the condition that a pH is larger than or equal to 8 to obtain an intermediate 3; 3) taking the intermediate 3, carbon disulfide and secondary amine, putting into a third organic solvent and performing reaction under the condition that a pH is larger than or equal to 8 to obtain a corresponding target compound crude product. The synthesizing method disclosed by the invention has the advantages of simpleness and easiness in operation, high yield and stable quality; the synthesized coumarin-dithiocarbamate derivative has better acetylcholine esterase inhibiting activity; a lead compound is provided for developing novel AD treating medicine.