57543-59-6

Usage

Uses

Used in Pharmaceutical Research:
8-Methoxy-2H-chromene-3-carboxylic acid is used as a potential drug candidate for its anti-inflammatory and anti-cancer properties. Its unique chemical structure allows it to modulate various biological pathways and target specific cellular processes, offering therapeutic benefits in treating inflammatory and cancerous conditions.
Used as an Intermediate in Organic Synthesis:
8-Methoxy-2H-chromene-3-carboxylic acid serves as an intermediate in the synthesis of other organic compounds. Its versatile chemical structure enables the development of new molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Agrochemicals:
In the field of agrochemicals, 8-Methoxy-2H-chromene-3-carboxylic acid has potential applications as a bioactive compound. Its ability to modulate biological pathways and target specific cellular processes can be harnessed to develop novel agrochemicals for crop protection and pest control.
Used in Materials Science:
8-Methoxy-2H-chromene-3-carboxylic acid also has potential applications in materials science. Its unique chemical structure and properties can be utilized to develop new materials with specific characteristics, such as optical, electronic, or mechanical properties, for various industrial applications.

InChI:InChI=1/C11H10O4/c1-14-9-4-2-3-7-5-8(11(12)13)6-15-10(7)9/h2-5H,6H2,1H3,(H,12,13)

Upstream product

• 548756-56-5 tert-butyl 3-hydroxy-3-(2-hydroxy-3-methoxyphenyl)-2-methylenenpropanoate 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 83823-29-4 8-Methoxy-2H-chromene-3-carboxylic acid amide 
• 57543-69-8 8‐methoxy‐2H‐chromene‐3‐carbonitrile 

Downstream Products

• 91520-00-2 8-methoxy-3,4-dihydro-2H-1-benzopyran-3-one 
• 108088-19-3 3,4-dihydro-8-methoxy-2H-1-benzopyran-3-carboxylic acid 
• 83823-31-8 8-Methoxy-2H-chromene-3-carboxylic acid [2-(3,4-dimethoxy-phenyl)-ethyl]-amide 
• 83823-30-7 (8-Methoxy-2H-chromen-3-yl)-(4-phenyl-piperazin-1-yl)-methanone 
• 83823-34-1 8-Methoxy-2H-chromene-3-carboxylic acid diphenylamide 
• 83823-48-7 1-(8-Methoxy-chroman-3-ylmethyl)-4-phenyl-piperazine 
• 83823-41-0 1-(8-Methoxy-2H-chromen-3-ylmethyl)-4-phenyl-piperazine 

Relevant academic research and scientific papers

6- and 8-Hydroxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyrans. Dopamine Agonists with Autoreceptor Selectivity

The dopamine agonist profiles of 3,4-duhydro-3-(3-dipropylamino)-2H-1-benzopyran-6- and 8-ol (4 and 5, respectively) were examined.Both 4 and 5 exhibited greater relative affinity for receptors labeled with the dopamine agonist ligand propylnorapomorphine than for those labeled with the dopamine antagonist ligand haloperidol.Both compounds attenuated the simulation of brain dopamine synthesis caused by γ-butyrolactone (GBL) and decreased the firing rate of substantia nigra dopamine neurons in rats.This profile of activity, together with the ability of the dopamine antagonist haloperidol to reverse the inhibition of dopamine neuronal firing, indicate that both compounds are brain dopamine agonists.

DUAL AGONISTS OF FXR AND PPARδ AND THEIR USES

The present invention relates to small molecule compounds and their use as agonists of farnesoid X receptor (FXR) and/or peroxisome proliferator activated receptor delta (PPARδ). The present invention also relates to the use of said compounds in the treatment of metabolic diseases and respective methods of treatment.

Bifunctional Br?nsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective Cα-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones

The catalytic asymmetric synthesis of both α-substituted and α,α-disubstituted (quaternary) β-tetralones through direct α-functionalization of the corresponding β-tetralone precursor remains elusive. A designed Br?nsted base-squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α-monosubstituted β-tetralones to nitroalkenes. Under these reaction conditions, not only enolization, and thus functionalization, occurs at the α-carbon atom of the β-tetralone exclusively, but adducts including all-carbon quaternary centers are also formed in highly diastereo- and enantioselective manner.

Synthesis of novel 2H-chromene-3-carboxylate isoxazole/isoxazoline derivatives via 1,3-dipolar cycloaddition reaction (NOAC)

Synthesis of novel (3-phenylisoxazol-5-yl)methyl-2H-chromene-3-carboxylates (7a–7d) and (3-phenyl-4,5-dihydroisoxazol-5-yl)methyl-2H-chromene-3-carboxylates (8a–8p) by 1,3-dipolar cycloaddition, and nitrile oxide and alkyne cycloaddition (NOAC) is presented. The products are characterised by IR, 1H and 13C NMR, and ESI-MS data.

Design and synthesis of chiral 2H-chromene-N-imidazolo-amino acid conjugates as aldose reductase inhibitors

Aldose reductase (ALR2) inhibitors provide a viable mode to fight against diabetic complications. ALR2 exhibit plasticity in the active site vicinities and possible shifts in the nearby two supporting alpha helices. Therefore, a novel series of amino acid conjugates of chromene-3-imidazoles (13–15) were designed and synthesized based on natural isoflavonoids. The compounds were identified on the basis of spectral (1H NMR,13C NMR and MS) data and tested in vitro for ALR2 inhibitory activity with an IC50value ranges from 0.031 ± 0.082 μM to 4.29 ± 0.55 μM. Our in silico and biochemical studies confirmed that 15e has the best inhibition activity among the synthesized compounds with a high selective index against the Aldehyde reductase (ALR1). Supplementation of 15e to STZ induced rats decreased the blood glucose levels and delayed the progression of cataract in a dose-dependent manner. The present study thus provides novel series of compounds with a promising inhibitor to prevent or delay the cataract progression.

Strong base- or acid-mediated chemoselectivity shifts in the synthesis of 2H-chromene or coumarin derivatives from common Baylis-Hillman adducts

Abstract Reaction of tert-butyl 3-(2-hydroxyphenyl)-2-methylenepropanoate esters with aqueous KOH provides convenient and chemoselective one-pot access to 2H-chromene-3-carboxylic acids, the overall transformation involving tandem conjugate addition, hydrolysis and elimination steps. The methodology complements the chemoselective, acid-catalysed route to 3-substituted coumarins from the same substrates by switching the regioselectivity of cyclisation.

Rational design and synthesis of novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazole derivatives as an anti-angiogenesis and anti-cancer agent

Based on earlier proven pharmacophore analogues of cancer a novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazoles (13-16) were rationally designed and synthesized by the reaction of chromene-3-carboxylic acids (10a-d) with substituted acyl bromides in the presence of TEA followed by refluxing with NH4OAc in toluene. Compounds 13-16 were screened in vitro for the inhibition of KRAS/Wnt and their anti-angiogenesis properties. Compound 16f has been identified as a potent anti-angiogenesis molecule, which can be considered as a new lead structure. The molecular docking analysis displayed the higher binding affinity of 16f with KRAS, Wnt and VEGF.

Novel 2-aminotetralin and 3-aminochroman derivatives as selective serotonin 5-HT7 receptor agonists and antagonists

The understanding of the physiological role of the G-protein coupled serotonin 5-HT7 receptor is largely rudimentary. Therefore, selective and potent pharmacological tools will add to the understanding of serotonergic effects mediated through t

Chromene and Chroman 3-Carboxamides and Some Related Compounds as a New Class of Centrally Acting Agents

A number of chromene-3-carboxamides (7), 3-Aminochromans (11) and 3-aminomethylchromans (9) have been synthesized.Chromene-3-carboxamides have been found to exhibit strong central muscle relaxant activity compared to mephesin.