588702-80-1

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3-dihydro-benzofuran-5-carboxylate is utilized as a key building block in the creation of diverse organic compounds. Its unique structure allows for its incorporation into complex molecules, facilitating the development of new chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Methyl 2,3-dihydro-benzofuran-5-carboxylate serves as an intermediate in the synthesis of drugs. Its presence in drug molecules can contribute to the desired therapeutic effects, including its noted antioxidant and antitumor properties, which are crucial for the development of medications targeting cancer and other diseases.
Used in Agrochemicals:
Methyl 2,3-dihydro-benzofuran-5-carboxylate is also applied in the agrochemical industry, where it is used as a component in the synthesis of various agrochemical products. Its role in these products can be attributed to its ability to enhance the effectiveness of pesticides, herbicides, and other agricultural chemicals, thereby supporting crop protection and yield enhancement.
Used in Antioxidant Applications:
Given its antioxidant properties, Methyl 2,3-dihydro-benzofuran-5-carboxylate is used to protect against oxidative stress. This application is relevant across various industries, including pharmaceuticals and cosmetics, where antioxidants are essential for maintaining the stability and efficacy of products, as well as for promoting health and wellness.
Used in Antitumor Research:
The antitumor potential of Methyl 2,3-dihydro-benzofuran-5-carboxylate positions it as a subject of interest in cancer research. It is studied for its possible role in the development of new therapeutic agents that could combat tumor growth, making it a valuable asset in the advancement of oncology treatments.

Upstream product

• 90843-31-5 1-(2,3-dihydrobenzofuran-5-yl)ethanone 
• 67-56-1 methanol 
• 55745-70-5 2,3-dihydro-benzofuran-5-carbaldehyde 
• 108763-47-9 5-(methoxycarbonyl)benzo[b]furan 
• 42113-13-3 methyl 4-hydroxy-3-methylbenzoate 
• 76429-73-7 2,3-dihydrobenzofuran-5-carboxylic acid 

Downstream Products

• 321195-99-7 2,3-dihydro-1-benzofuran-5-carbohydrazide 
• 90721-27-0 benzofuran-5-carboxylic acid 
• 108763-47-9 5-(methoxycarbonyl)benzo[b]furan 

Relevant academic research and scientific papers

Selective Hydrogenation of Benzofurans Using Ruthenium Nanoparticles in Lewis Acid-Modified Ruthenium-Supported Ionic Liquid Phases

Ruthenium nanoparticles immobilized on a Lewis-acid-functionalized supported ionic liquid phase (Ru?SILP-LA) act as effective catalysts for the selective hydrogenation of benzofuran derivatives to dihydrobenzofurans. The individual components (nanoparticles, chlorozincate-based Lewis-acid, ionic liquid, support) of the catalytic system are assembled using a molecular approach to bring metal and acid sites in close contact on the support material, allowing the hydrogenation of O-containing heteroaromatic rings while keeping the aromaticity of C6-rings intact. The chlorozincate species were identified to be predominantly [ZnCl4]2- anions using X-ray photoelectron spectroscopy and are in close interaction with the metal nanoparticles. The Ru?SILP-[ZnCl4]2- catalyst exhibited high activity, selectivity, and stability for the catalytic hydrogenation of a variety of substituted benzofurans, providing easy access to biologically relevant dihydrobenzofuran motifs under continuous flow conditions.

Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles

The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.

Imidazole-containing condensed tricyclic compound and application thereof

The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.

Tricyclic and fused-cyclic ALK (anaplastic lymphoma kinase) inhibitors

The invention belongs to the technical field of medicines, and particularly relates to tricyclic and fused-cyclic ALK (anaplastic lymphoma kinase) inhibitors represented in a general formula (I), pharmaceutically acceptable salts, esters and solvates of the tricyclic and fused-cyclic ALK inhibitors or stereoisomers of the tricyclic and fused-cyclic ALK inhibitors, wherein definitions of R, R, R, R, a ring A and a ring B are shown in the specification. The invention further relates to a preparation method of the compounds, pharmaceutic preparations and pharmaceutic composition which contain the compounds, as well as an application of the compounds, the pharmaceutically acceptable salts, esters and solvates of the compounds or the stereoisomers of the compounds in preparation of drugs for treating and/or preventing cancer related diseases mediated by ALK.

Design, synthesis and structure-activity relationships of 1,3,4-oxadiazole derivatives as novel inhibitors of glycogen synthase kinase-3β

Glycogen synthase kinase-3β (GSK-3β) is implicated in abnormal hyperphosphorylation of tau protein and its inhibitors are expected to be a promising therapeutic agents for the treatment of Alzheimer's disease. Here we report design, synthesis and structure-activity relationships of a novel series of oxadiazole derivatives as GSK-3β inhibitors. Among these inhibitors, compound 20x showed highly selective and potent GSK-3β inhibitory activity in vitro and its binding mode was determined by obtaining the X-ray co-crystal structure of 20x and GSK-3β.

2-{3-[4-(Alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole derivatives as novel inhibitors of glycogen synthase kinase-3β with good brain permeability

Glycogen synthase kinase 3β (GSK-3β) inhibition is expected to be a promising therapeutic approach for treating Alzheimer's disease. Previously we reported a series of 1,3,4-oxadiazole derivatives as potent and highly selective GSK-3β inhibitors, however,

NOVEL OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE

This invention relates to novel oxadiazolyl-diazabicyclononane derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors and modulators of the monoamine receptors and transporters. Due to their pharmacological profile the compounds of the invention may be useful for the treatment ofdiseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5- carboxamide, an agonist of the α7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: Synthesis and structure-activity relationship

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide (14, PHA-543,613), a novel agonist of the α7 neuronal nicotinic acetylcholine receptor (α7 nAChR), has been identified as a potential treatment of cognitive deficits in schizophrenia. Compound 14 is a potent and selective a7 nAChR agonist with an excellent in vitro profile. The compound is characterized by rapid brain penetration and high oral bioavailability in rat and demonstrates in vivo efficacy in auditory sensory gating and, in an in vivo model to assess cognitive performance, novel object recognition.

COMPOUNDS HAVING BOTH α7 NICOTINIC AGONIST ACTIVITY AND 5HT3 ANTAGONIST ACTIVITY FOR TREATMENT OF CNS DISEASES

The invention discloses compounds that are selective α7 nAChR agonists and 5-HT3 antagonists. The compounds are useful for treating many CNS diseases.

Azabicyclic compounds for the treatment of disease

The invention provides compounds of Formula I: 1wherein Azabicyclo is 2These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals in which α7 is known to be involved.