74083-58-2

Upstream product

• 141-52-6 sodium ethanolate 
• 105-53-3 diethyl malonate 
• 108-46-3 recorcinol 
• 542-05-2 acetonedicarboxylic acid 
• 62935-73-3 methyl 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetate 
• 150-19-6 O-methylresorcine 
• 77-92-9 citric acid 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 64-17-5 ethanol 
• 62935-72-2 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetic acid 
• 6950-82-9 2-(7-hydroxy-2-oxochromen-4-yl)acetic acid 

Downstream Products

• 95113-93-2 ethyl 8-(4-phenyl-1-piperazinylmethyl)-7-hydroxycoumarin-4-acetate 
• 911290-08-9 ethyl [7-(3-chlorobenzyl)oxy-2-oxo-2H-chromen-4-yl]acetate 
• 1427204-03-2 C₁₈H₁₄ClNO₆S 
• 911290-31-8 {7-[(3-chlorobenzyl)oxy]-2-oxo-2H-chromen-4-yl}acetonitrile 
• 911290-43-2 7-(benzyloxy)-4-(2-hydroxyethyl)-2H-chromen-2-one 

Relevant academic research and scientific papers

Photophysical, DFT and molecular docking studies of Sm(III) and Eu(III) complexes of newly synthesized coumarin ligand

Herein, [M(HL)2(H2O)2]NO3·2H2O (M = Sm (III) /or Eu (III); HL = 4-(2-hydroxy benzylidene acetohyrazide)-7-hydroxy coumarin) were synthesized and characterized using several spectroscopic methods. The complexes stoichiometry with molar ratio 2L:1M were confirmed by Job's method. Tridentate ligand (HL) was coordinated to the lanthanide ions Sm(III) or Eu(III) through azomethine nitrogen atom, phenolic oxygen of hydrazide, and ketonic oxygen of the amide group. The photophysical properties of the ligand and its complexes were studied in different organic solvents and their fluorescence quantum yields were determined as well. Strong fluorescence emissions to red shifts of europium complex were observed at 580, 593, 617, 653, 693, 704 nm which were attributed to Eu(III) emission of 5D0→7F0, 5D0→7F1, 5D0→7F2, 5D0→7F3, 5D0→7F4, and 5D0→7F5, respectively. First-principles DFT calculations were performed to evaluate the optimized structure and separation energies of the HL compound, using the B3LYP/6-311++g(d,p) basis set. Molecular docking studies were carried out to predict the binding modes between the HL compound and active site of the xanthine oxidase enzyme [ECNo. (1.17.3.2) PDB ID: 1FIQ] which produced from liver patients of hepatitis C. The observed activity of the HL gave rise to the conclusion that it might exert its action through inhibition of the xanthine oxidase enzyme.

Development of an iron-selective antioxidant probe with protective effects on neuronal function

Iron accumulation, oxidative stress and calcium signaling dysregulation are common pathognomonic signs of several neurodegenerative diseases, including Parkinsońs and Alzheimer's diseases, Friedreich ataxia and Huntington's disease. Given their therapeutic potential, the identification of multifunctional compounds that suppress these damaging features is highly desirable. Here, we report the synthesis and characterization of N-(1, 3-dihy-droxy-2-(hydroxymethyl) propan-2-yl)-2-(7-hydroxy-2-oxo-2H-chromen-4-yl) acetamide, named CT51, which exhibited potent free radical neutralizing activity both in vitroand in cells. CT51 bound Fe2+ with high selectivity and Fe3+ with somewhat lower affinity. Cyclic voltammetric analysis revealed irreversible binding of Fe3+ to CT51, an important finding since stopping Fe2+/Fe3+ cycling in cells should prevent hydroxyl radical production resulting from the Fenton-Haber-Weiss cycle. When added to human neuroblastoma cells, CT51 freely permeated the cell membrane and distributed to both mitochondria and cytoplasm. Intracellularly, CT51 bound iron reversibly and protected against lipid peroxidation. Treatment of primary hippocampal neurons with CT51 reduced the sustained calcium release induced by an agonist of ryanodine receptor-calcium channels. These protective properties of CT51 on cellular function highlight its possible therapeutic use in diseases with significant oxidative, iron and calcium dysregulation.

A selective fluorescent probe for the detection of mercury (II) in aqueous media and its applications in living cells

In this Letter we present a new probe, 2-amino-3-hydroxy-2-(hydroxymethyl) propyl 2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetate (PMR), which can reversibly detect mercuric ions (Hg2+) in HEPES buffer under physiological conditions. Possible interference with other analytes was examined. PMR displays a highly selective decrease of its fluorescence at 460 nm when it reacts with Hg2+. Interestingly, the probe can also be used as a fluorescent turn-on sensor for biologically relevant thiols such as glutathione and cysteine. PMR can be used to determine mercury in living cells.

Synthesis and Spectroscopic Properties of Fluorinated Coumarin Lysine Derivatives

The site-selective incorporation of fluorescent amino acids into proteins has emerged as a valuable alternative to expressible protein reporters. For successful application, a robust and scalable, yet flexible, route to non-natural amino acids is required. This work describes an improved synthesis of coumarin-conjugated lysine derivatives where fluorinated variants are accessed. These analogues can be utilized at low pH and should find application probing biological processes that operate under acidic conditions.

Discovery, biological evaluation, and structure-activity and -selectivity relationships of 6′-substituted (E)-2-(benzofuran-3(2H)-ylidene)-N- methylacetamides, a novel class of potent and selective monoamine oxidase inhibitors

The use of selective inhibitors of monoamine oxidase A (MAO-A) and B (MAO-B) holds a therapeutic relevance in the treatment of depressive disorders and Parkinson's disease (PD), respectively. Here, the discovery of a new class of compounds acting as monoamine oxidase inhibitors (MAO-Is) and bearing a 6′-substituted (E)-2-(benzofuran-3(2H)-ylidene)-N-alkylacetamide skeleton is reported. 6′-Sulfonyloxy derivatives exhibited outstanding affinities to MAO-A (7.0 nM 50 49 nM, much higher than moclobemide) and a pronounced MAO-A/B selectivity. The corresponding 6′-benzyloxy derivatives showed potent MAO-B inhibition and inverted selectivity profile. The rigid E-geometry of the exocyclic double bond allowed a more efficient binding conformation compared to more flexible and less active 2-(1-benzofuran-3-yl)-N- methylacetamide isomers and 4-N-methylcarboxamidomethylcoumarin analogues. Focused structural modifications and docking simulations enabled the identification of key molecular determinants for high affinity toward both MAO isoforms. These novel MAO-Is may represent promising hits for the development of safer therapeutic agents with a potential against depression, PD, and other age-related neurodegenerative pathologies.

Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: Development and biopharmacological profiling of 7-[(3-chlorobenzyl) oxy]-4-[(methylamino)methyl]-2H-chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor

In an effort to discover novel selective monoamine oxidase (MAO) B inhibitors with favorable physicochemical and pharmacokinetic profiles, 7-[(m-halogeno)benzyloxy]coumarins bearing properly selected polar substituents at position 4 were designed, synthesized, and evaluated as MAO inhibitors. Several compounds with MAO-B inhibitory activity in the nanomolar range and excellent MAO-B selectivity (selectivity index SI > 400) were identified. Structure-affinity relationships and docking simulations provided valuable insights into the enzyme-inhibitor binding interactions at position 4, which has been poorly explored. Furthermore, computational and experimental studies led to the identification and biopharmacological characterization of 7-[(3-chlorobenzyl)oxy]-4-[(methylamino)-methyl]-2H-chromen-2-one methanesulfonate 22b (NW-1772) as an in vitro and in vivo potent and selective MAO-B inhibitor, with rapid blood-brain barrier penetration, short-acting and reversible inhibitory activity, slight inhibition of selected cytochrome P450s, and low in vitro toxicity. On the basis of this preliminary preclinical profile, inhibitor 22b might be viewed as a promising clinical candidate for the treatment of neurodegenerative diseases.

KAl(SO4)2·12H2O (alum) a reusable catalyst for the synthesis of some 4-substituted coumarins via Pechmann reaction under solvent-free conditions

A simple, efficient, and practical procedure for the Pechmann condensation using KAl(SO4)2·12H2O (alum) as a non-toxic, reusable, inexpensive, and easily available catalyst is described under solvent-free condition at 65°C. These improved reaction conditions allow the preparation of a wide variety of some new substituted coumarins in high yields (86-96%) and purity under mild reaction conditions. Compared to the classical Pechmann condensation, this new method consistently has the advantage of high yields.

SUBSTITUTED AMINOALKYL- AND AMIDOALKYL-BENZOPYRAN DERIVATIVES

This invention is related to novel aminoalkyl- and amidoalkyl- b enzopyran derivatives of the following general formula (I) wherein: the group (a) is a substituent in position 6 or 7 wherein: R is amono- or bi-cyclic (C6-C10) aryl or

Solvent-free coumarin synthesis

The synthesis of coumarins via Pechmann and Knoevenagel condensation reactions under solvent-free conditions is reported, in which waste minimization, simple operation and easier product work-up can be achieved.

Environmentally friendly synthesis of coumarin derivatives employing heterogeneous catalysis

Zeolite H-BEA and other solid acids have been shown to be effective catalysts for the production of coumarin derivatives from activated phenols and acids or esters possessing an additional alkylation function, or β-keto esters (Pechmann reaction). These heterogeneous catalysts eliminate the production of acidic waste streams associated with conventional (Lewis) acid catalysts. Zeolite H-BEA proved to be the preferred catalyst.