35924-44-8

Upstream product

• 89228-62-6 N-hydroxy-6-methoxy-2-oxo-2H-1-benzopyran-3-carboxamide 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 141-82-2 malonic acid 
• 2033-24-1 cycl-isopropylidene malonate 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 133031-78-4 dipotassium 2,4-dimethoxybenzylidenemalonate 
• 150-76-5 4-methoxy-phenol 
• 105-53-3 diethyl malonate 
• 682805-95-4 2,4-dimethoxybenzylidenemalonic acid 
• 7324-86-9 ethyl 3-(2,4-dimethoxyphenyl)-2-ethoxycarbonyl-2-propenoate 
• 17580-69-7 2-hydroxy-5-methoxybenzaldehyde oxime 
• 41459-71-6 ethyl 6-methoxycoumarin-3-carboxylate 
• 117646-10-3 5-(2',5'-dimethoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 1366125-55-4 C₁₈H₁₆O₄S 

Relevant academic research and scientific papers

Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method

The invention relates to a method for synthesizing coumarin-3-carboxylic acid compounds by a one-pot two-step method. The structural formula of the coumarin-3-carboxylic acid compounds is shown in the description, wherein R1 is H , Cl , Br, NO2 , CH3 and HO . According to the synthesis process of the coumarin-3-carboxylic acid compounds, malonic acid, acetone and substituted salicylaldehyde serve as raw materials, iodine serves as a catalyst, acetic anhydride serves as a solvent, a series of coumarin-3-carboxylic acid compounds are synthesized through a one-pot cascade reaction, and the efficiency and the yield are greatly improved compared with a fractional step method.

Green synthesis method of coumarin-3-carboxylic acid compound

The invention relates to a green synthesis method of a coumarin-3-carboxylic acid compound. The synthesis process of the coumarin-3-carboxylic acid compound is as follows: R1 is H, Cl, Br, NO2, CH3 and HO. A series of coumarin-3-carboxylic acid compounds are synthesized in one step without a catalyst by taking R1-substituted salicylaldehyde and Meldrum's acid as raw materials and water as a reaction medium, the process steps are simple, the method has universality, reaction liquid can be repeatedly added for reaction, no waste or waste liquid is generated, the yield of a target product is greater than 54.3%, and the method is an environment-friendly green synthesis method.

3 - Coumarin formic acid compound and application thereof as antibacterial agent for preparing plant pathogenic bacteria

The invention relates to a compound with simple structure for inhibiting growth activity of phytopathogens, specifically relates to a 3-coumarin formic acid compound and application of the 3-coumarin formic acid compound as an antibacterial agent for preparing the phytopathogens, and discloses application of the 3-coumarin formic acid compound as the antibacterial agent for preparing the phytopathogens. The two 3-coumarin formic acid compounds has the following characteristics of molecular structure: the formulas are as shown in the specification, wherein R is hydrogen, methyl, methoxyl, hydroxyl, halogen and nitryl. The in vitro inhibitory activity of twenty-eight synthetic target compounds on four common plant pathogenic fungi such as apple decay pathogenic bacteria, apple ring spot pathogenic bacteria, maize curvularia pathogenic bacteria and potato dry rot pathogenic bacteria is measured by adopting a hypha linear growth rate method, so that the condition that all compounds have different inhibiting effects on supplied experimental bacteria is found.

Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin

Antioxidants have been the subject of intense research interest due to their numerous health benefits. In this work, a series of new conjugates of hydroxytyrosol and coumarin were synthesized and evaluated for their free radical scavenging, toxicity and antioxidant mechanism in vitro. The all target compounds 14a–t exhibited better radical scavenging activity than BHT, hydroxytyrosol, and coumarin in both DPPH radical and ABTS+ radical cation scavenging assays. The structure-activity relationships study indicated that the number and position of hydroxyl groups on the coumarin ring were vital to a good antioxidant capacity. Furthermore, the most promising compound 14q showed less toxicity in hemolysis assay and weaker antiproliferative effects than BHT against normal WI-38 and GES cells, and enhanced viability of H2O2-induced HepG2 cells. Additionally, 14q decreased the apoptotic percentage of HepG2 cells, reduced the ROS produce and LDH release, and improved GSH and SOD levels in H2O2-treated HepG2 cells. Lastly, 14q exhibited more stability than hydroxytyrosol in methanol solution. These results revealed that conjugations of hydroxytyrosol and coumarin show better antioxidant capacity, and are the efficacious approach to finding novel potential antioxidant.

Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity

A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.

A Primary Amide-Functionalized Heterogeneous Catalyst for the Synthesis of Coumarin-3-carboxylic Acids via a Tandem Reaction

A crystalline primary amide-based bifunctional heterogeneous catalyst, {[Cd2(2-BPXG)(Fum)2(H2O)2]·2H2O}n (1) (where, 2-BPXG = 2,2′-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl)) diacetamide and Fum = fumarate), has been developed for the one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids at room temperature via a Knoevenagel-intramolecular cyclization tandem reaction. Catalyst 1 is prepared at room temperature from a one-pot self-assembly process in 81% yield and high purity within a few hours and has a ladder-like polymeric architecture based on single-crystal X-ray diffraction. Additional characterization of 1 includes elemental analysis, infrared spectroscopy, thermogravimetric analysis, and powder X-ray diffraction. Based on the optimized conditions, it is determined that 1 is highly efficient (conditions: 2 mol % catalyst, 3 h, and 26-28 °C in methanol) for this reaction. Its recyclability up to five cycles without significant loss of activity and structural integrity is also demonstrated. Using both electron-donating and electron-withdrawing substituents on the salicylaldehyde substrate, seven different derivatives of coumarin-3-carboxylic acid were made. Additionally, the monoamine oxidase (MAO) inhibitor, coumarin-3-phenylcarboxamide, has also been synthesized from coumarin-3-carboxylic acid obtained in the catalysis process. A detailed mechanism of action is also provided.

Coumarin hybrid pyridinone amide derivative with potential anti-AD activity and preparation method and application of derivative

The invention discloses a coumarin hybrid pyridinone amide derivative and a preparation method and application thereof. The coumarin hybrid pyridinone amide derivative and pharmacologically acceptablesalt thereof are shown in the formula (I) and the formula (II), and the derivative can be used for preparing drugs for resisting the Alzheimer's disease, the Parkinson's disease or treating other diseases or symptoms by suppressing monoamine oxidase, chelating metallic iron ions, resisting A and resisting oxidation.

Coumarin-sesamol bio-based photoinitiator and preparation method thereof

The invention provides a coumarin-sesamol photoinitiator and a preparation method thereof. The initiator provided by the invention has good absorption performance under a light source with the wavelength being 200-450 nm, the absorption band covers an ultraviolet region and extends to a visible region, and the initiator can be used as an ultraviolet/visible light initiator; at the same time, the reaction conditions are mild, and the structural body is a bio-based material. The initiator provided by the invention is short in preparation route, high in purity (more than 95%), good in stability and high in sensitivity, the absorption band covers the ultraviolet region and part of the visible light region, and the initiator can be used in the field of 3D printing, and is a universal type photoinitiator with excellent performance.

Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-carboxamide-N-morpholine Hybrids as New Anti-Alzheimer Agents

A new series of coumarin-3-carboxamide-N-morpholine hybrids 5a–5l was designed and synthesized as cholinesterases inhibitors. The synthetic approach for title compounds was started from the reaction between 2-hydroxybenzaldehyde derivatives and Meldrum's acid to afford corresponding coumarin-3-carboxylic acids. Then, amidation of the latter compounds with 2-morpholinoethylamine or N-(3-aminopropyl)morpholine led to the formation of the compounds 5a–5l. The in vitro inhibition screen against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) revealed that most of the synthesized compounds had potent AChE inhibitory while their BuChE inhibitions are moderate to weak. Among them, propylmorpholine derivative 5g (N-[3-(morpholin-4-yl)propyl]-2-oxo-2H-chromene-3-carboxamide) bearing an unsubstituted coumarin moiety and ethylmorpholine derivative 5d (6-bromo-N-[2-(morpholin-4-yl)ethyl]-2-oxo-2H-chromene-3-carboxamide) bearing a 6-bromocoumarin moiety showed the most activity against AChE and BuChE, respectively. The inhibitory activity of compound 5g against AChE was 1.78 times more than that of rivastigmine and anti-BuChE activity of compound 5d is approximately same as rivastigmine. Kinetic and docking studies confirmed the dual binding site ability of compound 5g to inhibit AChE.

Coumarins and adenosine receptors: New perceptions in structure–affinity relationships

Adenosine receptor (AR) subtypes are involved in several physiological and pharmacological processes. Ligands that are able to selectively modulate one receptor subtype can delay or slow down the progression of diverse diseases. In this context, our research group focused its investigation into the discovery and development of novel, potent and selective AR ligands based on coumarin scaffold. Therefore, a series of 3-phenylcarboxamidocoumarins were synthesized and their affinity for the human AR subtypes was screened by radioligand binding assays for A1, A2A and A3 receptors and for A2B by adenylyl cyclase assay. Compound 26 was found to be the most remarkable, with a hA1/hA3 and hA2A/hA3 selectivity of 42, for the A3 AR (Ki?=?2.4?μm). Receptor-driven molecular modelling studies have provided valuable information on the binding/selectivity data of compound 26 and for the following optimization process. Moreover, compound 26 presents drug-like properties according to the general guidelines linked to the concept.