59276-88-9

Upstream product

• 2555-20-6 8-methoxy-2-oxo-2H-chromene-3-carboxylic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1588925-76-1 methyl (E)-3-(2,3-dimethoxyphenyl)-2-(4-methoxyphenyl)propenoate 
• 1588925-73-8 (E)-3-(2,3-dimethoxyphenyl)-2-(4-methoxyphenyl)propenoic acid 
• 104-01-8 4-Methoxyphenylacetic acid 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 696-62-8 para-iodoanisole 
• 95332-01-7 2-hydroxy-4',8-dimethoxyisoflav-3-ene 
• 42945-78-8 2-(4-methoxy-phenyl)-1-morpholin-4-yl-ethanethione 

Downstream Products

• 24051-96-5 8-hydroxy-3-(4'-hydroxy)phenylcoumarin 
• 10475-19-1 7-methoxy-2-(4-methoxyphenyl)benzofuran 

Relevant academic research and scientific papers

Structure-Based Optimization of Coumarin hA3 Adenosine Receptor Antagonists

Adenosine receptors participate in many physiological functions. Molecules that may selectively interact with one of the receptors are favorable multifunctional chemical entities to treat or decelerate the evolution of different diseases. 3-Arylcoumarins

Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones

A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

A transition-metal-free fast track to flavones and 3-arylcoumarins

A highly regioselective and transition-metal free one-pot arylation of chromenones with arylboronic acids has been achieved employing K2S2O8. The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.

Synthesis and Evaluation of Coumarin-Resveratrol Hybrids as 15-Lipoxygenaze Inhibitors

A series of coumarin-resveratrol hybrids, 3-arylcoumarin derivatives 3a-u, were synthesized through the intermolecular condensation reaction of various salicylaldehydes and phenylacetic acids in the presence of 1,4-diazabicyclo[2.2.2]octane under solvent-free conditions. All the synthesized compounds were screened for their inhibitory potency against soybean 15-lipoxygenase. Among them, three compounds (3c, 3j, and 3q) showed good enzyme-inhibitory activities. GRAPHICAL ABSTRACT.

Synthesis of 3-arylcoumarins by FeCL3-promoted cyclization of orto-methoxy-substituted (E)-2,3-diphenylpropenoic acids or their methyl esters

3-Arylcoumarins were conveniently synthesized in excellent yields by an iron(III) chloride-promoted tandem reaction using methoxy-substituted (E)-2,3-diphenylpropenoic acids or their methyl esters. The structure of 3-(4-methoxyphenyl)coumarin was establis

3-Arylcoumarins: Synthesis and potent anti-inflammatory activity

Chronic inflammation is the persistent and excessive immune response and can lead to a variety of diseases. Aiming to discover new compounds with anti-inflammatory activity, we report herein the synthesis and biological evaluation of 3-arylcoumarins. Thirty five 3-arylcoumarins were prepared through Perkin condensation and further acid-promoted hydrolysis if necessary. In lipopolysaccharide-activated mouse macrophage RAW264.7 cells, 6,8-dichloro-3-(2-methoxyphenyl)coumarin (16) and 6-bromo-8-methoxy-3-(3-methoxyphenyl)coumarin (25) exhibited nitric oxide production inhibitory activity with the IC50 values of 8.5 μM and 6.9 μM, respectively, providing a pharmacological potential as anti-inflammatory agents.

Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins

In the present work we synthesized a series of hydroxy-3-arylcoumarins (compounds 1-9), some of them previously described as MAO-B selective inhibitors, with the aim of evaluating their antioxidant properties. Theoretical evaluation of ADME properties of all the derivatives was also carried out. From the ORAC-FL, ESR and CV data it was concluded that these derivatives are very good antioxidants, with a very interesting hydroxyl, DPPH and superoxide radicals scavenging profiles. In particular compound 9 is the most active and effective antioxidant of the series (ORAC-FL = 13.5, capacity of scavenging hydroxyl radicals = 100%, capacity of scavenging DPPH radicals = 65.9% and capacity of scavenging superoxide radicals = 71.5%). Kinetics profile for protection fluorescein probe against peroxyl radicals by addition of antioxidant molecule 9 was also performed. Therefore, it can operate as a potential candidate for preventing or minimizing the free radicals overproduction in oxidative-stress related diseases.

MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, invitro Study, and Docking Calculations

Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3-arylcoumarin derivatives were previously described as interesting selective MAO-B inhibitors. Preserving the trans-stilbene structure, a series of 2-arylbenzofuran and corresponding 3-arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO-A and MAO-B. In general, both types of derivatives were found to be selective MAO-B inhibitors, with IC50 values in the nano- to micromolar range. 5-Nitro-2-(4-methoxyphenyl)benzofuran (8) is the most active compound of the benzofuran series, presenting MAO-B selectivity and reversible inhibition (IC50=140nM). 3-(4′-Methoxyphenyl)-6-nitrocoumarin (15), with the same substitution pattern as that of compound 8, was found to be the most active MAO-B inhibitor of the coumarin series (IC50=3nM). However, 3-phenylcoumarin 14 showed activity in the same range (IC50=6nM), is reversible, and also severalfold more selective than compound 15. Docking experiments for the most active compounds into the MAO-B and MAO-A binding pockets highlighted different interactions between the derivative classes (2-arylbenzofurans and 3-arylcoumarins), and provided new information about the enzyme-inhibitor interaction and the potential therapeutic application of these scaffolds.

Palladium-catalyzed decarboxylative cross-coupling reactions: A route for regioselective functionalization of coumarins

A straightforward, regioselective, and step-economical ligand-free palladium-catalyzed decarboxylative functionalization of coumarin-3-carboxylic acids is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows for construction of various biologically important π-electron extended coumarins.

A New Synthesis of 3-Arylcoumarins: Synthesis of Coumestan

Reaction of thioacetomorpholides with POCl3 furnishes complexes which on reaction with salicylaldehydes afford 3-arylcoumarins (1a-h).The arylcoumarin (1h) has been converted into coumestan (5).