223420-30-2

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONE is used as a potential pharmaceutical compound for its possible biological and chemical reactivity, which may contribute to the development of new drugs or therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, 6-CHLORO-4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONE may be utilized as a precursor or active ingredient in the development of new pesticides, herbicides, or other agricultural chemicals, due to its unique chemical structure.
Used in Material Science:
6-CHLORO-4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONE could be employed in material science for the synthesis of new materials with specific properties, such as improved stability, reactivity, or other characteristics that may be beneficial in various applications.

Upstream product

• 95-88-5 4-Chlororesorcinol 
• 223420-33-5 6-bromo-4-(chloromethyl)-7-hydroxy-2H-chromen-2-one 
• 638-07-3 ethyl (2-chloroaceto)acetate 

Downstream Products

• 1011625-29-8 C₁₈H₁₃ClN₂O₃S 

Relevant academic research and scientific papers

A new synthetic protocol for coumarin amino acid

The hydrochloride of the racemic amino acid (2-(7-hydroxycoumarin-4-yl) ethyl)glycine, which can serve as a fluorescent probe in proteins, and two halogen derivatives of it, were synthesized by using a new synthetic protocol in five steps. It is less costly and relatively easy to prepare this kind of fluorescent amino acid with the new synthetic method. Furthermore, it can be applied to synthesize other derivatives of the coumarin amino acid with some specific properties.

Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin

Sialin, encoded by the SLC17A5 gene, is a lysosomal sialic acid transporter defective in Salla disease, a rare inherited leukodystrophy. It also enables metabolic incorporation of exogenous sialic acids, leading to autoantibodies against N-glycolylneuraminic acid in humans. Here, we identified a novel class of human sialin ligands by virtual screening and structure-activity relationship studies. The ligand scaffold is characterized by an amino acid backbone with a free carboxylate, an N-linked aromatic or heteroaromatic substituent, and a hydrophobic side chain. The most potent compound, 45 (LSP12-3129), inhibited N-acetylneuraminic acid 1 (Neu5Ac) transport in a non-competitive manner with IC50 ≈ 2.5 μM, a value 400-fold lower than the KM for Neu5Ac. In vitro and molecular docking studies attributed the non-competitive character to selective inhibitor binding to the Neu5Ac site in a cytosol-facing conformation. Moreover, compound 45 rescued the trafficking defect of the pathogenic mutant (R39C) causing Salla disease. This new class of cell-permeant inhibitors provides tools to investigate the physiological roles of sialin and help develop pharmacological chaperones for Salla disease.

Coumarin-Caged Compounds of 1-Naphthaleneacetic Acid as Light-Responsive Controlled-Release Plant Root Stimulators

Six coumarin-caged compounds of 1-naphthaleneacetic acid (NAA) comprising different substituents on the coumarin moiety were synthesized and evaluated for their photophysical and chemical properties as light-responsive controlled-release plant root stimulators. The 1H NMR and HPLC techniques were used to verify the release of NAA from the caged compounds. After irradiation at 365 nm, the caged compounds exhibited the fastest release rate at t1/2 of 6.7 days and the slowest release rate at t1/2 of 73.7 days. Caged compounds at high concentrations (10-5 and 10-6 M) significantly stimulate secondary root germination while free NAA at the same level is toxic and leads to inhibition of secondary root germination. The cytotoxicity of the caged compounds against fibroblasts and vero cells were evaluated, and the results suggested that, at 10-5-10-6 M, caged compounds exhibited no significant cytotoxicity to the cells. Thus, the caged compounds of NAA in this study could be of great benefit as efficient agrochemicals.

Chasing ChEs-MAO B Multi-Targeting 4-Aminomethyl-7-Benzyloxy-2H-Chromen-2-ones

A series of 4-aminomethyl-7-benzyloxy-2H-chromen-2-ones was investigated with the aim of identifying multiple inhibitors of cholinesterases (acetyl- and butyryl-, AChE and BChE) and monoamine oxidase B (MAO B) as potential anti-Alzheimer molecules. Starting from a previously reported potent MAO B inhibitor (3), we studied single-point modifications at the benzyloxy or at the basic moiety. The in vitro screening highlighted triple-acting compounds (6, 8, 9, 16, 20) showing nanomolar and selective MAO B inhibition along with IC50 against ChEs at the low micromolar level. Enzyme kinetics analysis toward AChE and docking simulations on the target enzymes were run in order to get insight into the mechanism of action and plausible binding modes.

CAGED COMPOUND AND COMPOSITE

PROBLEM TO BE SOLVED: To provide a caged compound. SOLUTION: The compound is represented by formula (I) or (II) (where Z's are the same or different and each represent a biotinyl group or a maleimide group; Y represents a divalent linker group; Ar represents an optionally substituted arylene group or an optionally substituted heteroarylene group; and Ar1 represents an optionally substituted aryl group or an optionally substituted heteroaryl group). COPYRIGHT: (C)2015,JPOandINPIT

Synthesis and properties of 4-(3-aminothieno-[2,3-b]pyridin-2-yl)coumarins

Substituted 4-[(3-cyanopyridin-2-yl)thiomethyl]coumarins have been synthesized by the alkylation of 2-mercapto-4,6-dimethylnicotinonitrile with 4-chloromethylcoumarins. Substituted 4-(3-amino-thieno[2,3-b]pyridin-2-yl) coumarins have been obtained by a subsequent intramolecular condensation of the methylene and cyano groups. 6H-Chromeno[4,3-d]thieno[3,2-b:5,4-b']dipyridin-6- ones were isolated as a result of the interaction of these compounds with aldehydes, and their aminomethyl derivatives were synthesized.

PROTECTING GROUPS WITH INCREASED PHOTOSENSITIVITIES

Protecting groups derived from a halogenated coumarin group, a quinoline-2-one group, a xanthene group, a thioxanthene group, a selenoxanthene group, or an anthracene group are described. The protecting groups is photolabile and can be removed by irradiating the group with light, such as flash photolysis with ultraviolet radiation or pulsed infrared radiation.