5725-79-1

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 13948-45-3 3-acetamido-4-hydroxycoumarin 
• 5876-91-5 2-(methoxymethyloxy)benzoic acid 
• 81327-41-5 5-(2-Methoxymethoxy-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 52140-71-3 4-hydroxy-3-phenylazo-cumarine 
• 20261-31-8 4-hydroxy-3-nitrocoumarin 

Downstream Products

• 1026067-78-6 C₁₈H₁₅NO₅ 
• 1026067-72-0 C₁₈H₁₅NO₆ 
• 893632-35-4 C₁₈H₁₅NO₆ 
• 90515-49-4 N-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-3,4,5-trimethoxy-benzamide 
• 1573010-32-8 N⁽¹⁾-(4-hydroxy-2-oxo-2H-chromen-3-yl)-N⁽¹⁰⁾-phenyldecanediamide 
• 1573010-35-1 N⁽¹⁾-(4-hydroxy-2-oxo-2H-chromen-3-yl)-N⁽¹⁰⁾-(4-hydroxyphenyl)decanediamide 
• 101727-50-8 N-(4-hydroxycoumarin-3-yl)benzamide 

Relevant academic research and scientific papers

Targeting adenosine receptors with coumarins: Synthesis and binding activities of amide and carbamate derivatives

Objectives With the aim of finding the structural features governing binding activity and selectivity against adenosine receptors (ARs), several 3-subtituted coumarins with amide (compounds 3-6) and carbamate (7-9) functions were synthesized. To study its possible influence on the binding activity and selectivity, a hydroxyl substituent was also introduced at position 4 of the coumarin moiety. Methods A new series of coumarins (3-9) were synthesized and evaluated by radioligand binding studies towards ARs. Key findings None of the 4-hydroxy derivatives (4, 8 and 9) showed binding affinity for any of the ARs. None of the compounds interacted with the hA2B AR (Ki > 100 000 nm). Compounds 3, 5, 6 and 7 had different activity profiles with dissimilar binding affinity and selectivity towards human A1, A 2A and A3 ARs. Conclusions The most remarkable derivative is compound 7, which presents the best affinity and selectivity for the A 3 adenosine receptor (Ki = 5500 nm).

Multifunctional 3-Schiff base-4-hydroxycoumarin derivatives with monoamine oxidase inhibition, anti-β-amyloid aggregation, metal chelation, antioxidant and neuroprotection properties against Alzheimer's disease

A series of 3-Schiff base-4-hydroxycoumarin derivatives (1-20) have been designed, synthesized and evaluated as multifunctional agents against Alzheimer's disease. In vitro studies indicated that most of the derivatives exhibited significant abilities to inhibit monoamine oxidase (MAO), self-induced and Cu2+-induced β-amyloid (Aβ1-42) aggregati006Fn, as well acting as potential biometal chelators and antioxidants. Moreover, these derivatives were capable of decreasing reactive oxygen species (ROS) and showed good neuroprotective effects in PC12 cells and could penetrate the central nervous system (CNS). In particular, compound 4 exhibited high potency to monoamine oxidase (IC50, 0.673 μM for hMAO-A, 0.711 μM for hMAO-B), good antioxidant activity (1.34 trolox equivalents by ABTS method, 45.8 μM of IC50 by DPPH method), and it also displayed a significant ability to inhibit self-induced and Cu2+-induced Aβ1-42 aggregation (60.1%, 20 μM and 45.7%, 50 μM). Taken together, these results suggested that compound 4 might be a promising lead compound with balanced properties for AD treatment.

A convergent paired electrochemical synthesis of new heterocyclic compounds. Reaction of benzoquinones with 3-Amino-4-hydroxycoumarin

Electrochemical oxidation of catechols (1) has been studied in the presence of cathodically generated 3-amino-4- hydroxycoumarin (3a) as a nucleophile in aqueous solutions, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the o-benzoquinones derived from catechols (1) participate in Michael addition reaction with 3-amino-4- hydroxycoumarin (3a) to form the corresponding new heterocyclic compounds (7) (oxidized form of coumestan derivatives). The electrochemical process consists of a multi-step including (a) cathodic reduction of 4-hydroxy-3-nitrocoumarin (3) to 3-amino-4- hydroxycoumarin (3a), (b) anodic oxidation of catechols (1) to related o-benzoquinone (2), (c) the Michael addition reaction of 3- amino-4-hydroxycoumarin (3a) to o-benzoquinone (2), and (d) anodic oxidation of formed adduct. The paired electrochemical synthesis of compounds 7a and 7b has been successfully performed in a one-pot process at carbon rods as working and counter electrodes in an undivided cell.

Evaluation of trypanocidal and antioxidant activities of a selected series of 3-amidocoumarins

Background: Neglected diseases are becoming more prevalent due to globalization. This has inspired active research in the development of new drugs for the treatment of parasitic diseases such as Chagas disease. Objectives: With the aim of finding new tryp

Highly selective light-up Al3+ sensing by a coumarin based Schiff base probe: Subsequent phosphate sensing DNA binding and live cell imaging

A coumarin based simple fluorescent “turn-on” probe, 4-Hydroxy-3-[(2-hydroxy-5-methoxybenzylidene)-amino]-chromen-2-one (HMC), to detect metal ion based on the chelation enhanced fluorescence (CHEF), was synthesized by condensing 3-amino-4-hydroxycoumarin and 2-hydroxy-5-methoxybenzaldehyde. It was found to be highly selective and sensitive sensor for Al3+ in 90% aqueous methanol (MeOH: 0.01?M HEPES Buffer; 9:1; v/v) at pH 7.4 in fluorescence spectroscopy. Fluorescence intensity enhancement along with 10?nm blue shift was observed only in the presence of Al3+. The HMC binds Al3+ in 1:1 stoichiometry with a binding constant, Ka?=?(9.9?±?0.04)?×?103?M?1 and the detection limit was calculated to be as low as 1.62?μM. The binding mode of interaction with Al3+ and the chelate complex formation was supported with the help of a 1H NMR spectroscopy titration, ESI–MS and also by theoretical studies. Moreover, the HMC·Al3+ ensemble subsequently detected the biologically important phosphate ions and nucleotides via fluorescence quenching. The live cell imaging study indicated that HMC is highly efficient in the detection of exogenous Al3+ in living cell.

A coumarin based Schiff base probe for selective fluorescence detection of Al3?+ and its application in live cell imaging

A new coumarin based Schiff base compound, CSB-1 has been synthesized to detect metal ion based on the chelation enhanced fluorescence (CHEF). The cation binding properties of CSB-1 was thoroughly examined in UV–vis and fluorescence spectroscopy. In fluorescence spectroscopy the compound showed high selectivity toward Al3?+ ion and the Al3?+ can be quantified in mixed aqueous buffer solution (MeOH: 0.01?M HEPES Buffer; 9:1; v/v) at pH?7.4 as well as in BSA media. The fluorescence intensity of CSB-1 was enhanced by ~?24 fold after addition of only five equivalents of Al3?+. The fluorescence titration of CSB-1 with Al3?+ in mixed aqueous buffer afforded a binding constant, Ka?=?(1.06?±?0.2)?×?104?M??1. The colour change from light yellow to colourless and the appearance of blue fluorescence, which can be observed by the naked eye, provides a real-time method for Al3?+ sensing. Further the live cell imaging study indicated that the detection of intracellular Al3?+ ions are also readily possible in living cell.

New Coumarin Derivatives as Anti-Breast and Anti-Cervical Cancer Agents Targeting VEGFR-2 and p38α MAPK

Breast and cervical cancers are the most common gender-specific cancers affecting women worldwide. In this investigation, we highlighted the synthesis, VEGFR-2 and p38α MAPK inhibitory activity of new series of fluorinated coumarin-based derivatives featuring a variety of bioactive chemical moieties attached or fused to the coumarin nucleus at the 3 and/or 4 position. The bioactive inhibitors were further assessed for their anti-proliferative effect against human MCF-7 breast cancer and HeLa cervical cancer cell lines, respectively. Most of the tested compounds showed potent preferential inhibition effects against human VEGFR-2 and remarkable anticancer activities in the human breast cancer cell line MCF-7. Compounds 29, 24, and 2 displayed the highest inhibitory activity against VEGFR-2 (94% inhibition) and they were the most potent anticancer agents toward MCF-7 cancer cells with IC50 values of 7.90, 8.28, and 8.30 μg/mL, respectively. Compound 13 inhibited p38α MAPK phosphorylation with a significant reduction in % cell viability against HeLa cancer cells at 10 and 30 μM. Docking experiments carried out on VEGFR-2 and p38 MAPK crystallographic structures revealed that the active compounds bind to the active sites through H-bonds, arene–cation, and hydrophobic π–π interactions. QSAR analysis demonstrated considerable correlation coefficient (R2 = 0.76969) and root mean square error (RMSE = 0.10446) values. Also, the residual values between the experimental pIC50 and predicted pIC50 are very close, indicating the reliability of the established QSAR model.

Pseudo three-component approach to coumarin-annulated azepines: Synthesis of coumarin[3,4-: B] azepines

A series of coumarin-annulated azepines were synthesized via acid-catalyzed condensation of 3-amino-4-hydroxycoumarin with two equivalents of substituted acetophenones in toluene with moderate to good yields. A plausible mechanism for this pseudo three-component reaction was proposed.

4 - hydroxy coumarin - 3 - sheaff alkali derivatives and their use for treating Alzheimer's disease

The invention relates to the field of medicinal chemistry, in particular to a 4-hydroxycoumarin-3-Schiff base compound (I). Pharmacodynamic experiments prove that the compound is a multifunctional monoamine oxidase (MAO) inhibitor, has better effects of i

Development of novel adenosine receptor ligands based on the 3-amidocoumarin scaffold

With the aim of finding new adenosine receptor (AR) ligands presenting the 3-amidocoumarin scaffold, a study focusing on the discovery of new chemical entities was carried out. The synthesized compounds 1-8 were evaluated in radioligand binding (A1/