41459-71-6

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 105-53-3 diethyl malonate 
• 18224-54-9 ethyl 3,3-bis(ethylsulfanyl)acrylate 
• 3702-98-5 ethyl 4,4,4-trichloroacetoacetate 
• 150-76-5 4-methoxy-phenol 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 41459-72-7 6-methoxy-2-oxo-2H-chromene-3-carbonitrile 
• 35924-44-8 6-methoxycoumarin-3-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of 3-arylated 3,4-dihydrocoumarins: Combining continuous flow hydrogenation with laccase-catalysed oxidation

A convenient arylation of diverse 3,4-dihydrocoumarins with a number of catechols is described leading to a new class of compounds. As key step, a laccase-catalysed oxidation/Michael addition sequence is applied using commercially available laccase from Agaricus bisporus. 3,4-Dihydrocoumarins were obtained in a rapid and facile two-step sequence starting from salicylaldehydes: The corresponding coumarins were synthesised through a Knoevenagel condensation in up to 83% yield followed by a quantitative reduction performed in a flow system. Combining the reductive flow reaction with the laccase-catalysed arylation also led to successful consecutive one-pot approaches. Overall, the enzyme-catalysed arylations were carried out with yields ranging from 63 to 94%.

Synthesis, crystal structure, spectroscopic characterization and anti-fungal activity of Ethyl 2-Oxo-2H-chromene-3-carboxylateDerivatives

Ethyl 2-oxo-2H-chromene-3-carboxylate derivatives were synthesized and characterized by FT-IR, NMR, MS and X-ray crystal diffraction. Compound 3d crystallizes in the triclinic system with space group P-1. Compound 3e crystallizes in the monoclinic system with space group P21/c. The potential anti-fungal activities have been studied against five kinds of common fungi at concentrations of 200 ppm and 500 ppm. The research showed that the target compounds exhibit certain anti-fungal activity against the tested fungal strains. The inhibition rate of compound 3b was the highest against Fusarium oxysporum, up to 60.29% at 500 ppm. Compound 3b is promising to become the lead compound of pesticide in the future, which is worthy of further study.

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 facile, efficient and solvent-free titanium (IV) ethoxide catalysed knoevenagel condensation of aldehydes and active methylenes

Titanium ethoxide has been employed as a novel and efficient reagent for the Knoevenagel condensation of aldehydes with active methylenes such as diethyl malonate and ethyl cyanoacetate under solvent free conditions to afford substituted olefins in high to excellent yields. The reaction is suitable for a variety of aromatic, aliphatic and heteroaromatic aldehydes with various active methylenes. Parallel to this, microwave irradiation has been utilized to achieve improved reaction rates and enhanced yields. Herein, we illustrated a convenient method for the preparation of α,β-unsaturated compounds using both conventional and microwave irradiation methods. An efficient and solvent free Knoevenagel condensation between aldehydes and active methylenes was developed using titanium ethoxide. The procedure proved to be successful with a wide range of substrates such as aromatic, aliphatic and heterocyclic aldehydes and various active methylenes to afford substituted olefins. The reaction was also carried out under microwave irradiation to accomplish the corresponding olefins with improved reaction rates, yields and cleaner reaction profiles.We have developed an efficient and novel methodology for the synthesis of olefinic compounds by Knoevenagel condensation under solvent-free conditions using titanium ethoxide, for the first time, as a reagent as well as a solvent. This method is appropriate for the synthesis of a variety of aromatic aldehydes containing various electron-donating and withdrawing groups, aliphatic and heteroaromatic aldehydes. The significant advantages offered by this methodology could be applied to various active methylenes in order to offer the corresponding Knoevenagel products. Thus, we believe that this method delivers high conversions, cleaner reaction profiles under solvent-free reaction conditions and shorter reaction times, all of which make it a very useful and attractive approach for the preparation of a wide range of substituted olefins.

Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives

Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side

Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins

A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.

Organic–inorganic hybrid material, dichloro N,N'-(1,2-phenylene)bis(2-aminobenzamide) cobalt(II)@Al-SBA-15: an environment friendly catalyst for the synthesis of 3-benzoxazol-2-yl-chromen-2-ones

A new organic-inorganic hybrid material, CoCl2N,N'-(1,2-phenylene)bis(2-aminobenzamide)@Al-SBA-15, was synthesized by modification of Al-SBA-15 with (3-chloropropyl) trimethoxysilane (CPTMS), then the ligand was covalently attached to CPTMS@Al-SBA-15 and finally addition of CoCl2 to form the complex. The mesoporous CoCl2NN'PhBIA@Al-SBA-15 was an efficient catalyst in the preparation of 3-benzoxazol-2-yl-chromen-2-one derivatives through reaction of different coumarin-3-carboxylates and 2-aminophenol derivatives. The nanocatalyst increased rate and facility of the aforementioned reaction and had influence in the green synthesis of different 3-benzoxazol-2-yl-2H-chromen-2-one derivatives. The nanocatalyst was characterized by N2 adsorption–desorption, Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), and energy dispersive spectroscopy (EDS). Some advantages of this procedure are mild reaction condition, high yields of 3-benzoxazol-2-yl-2H-chromen-2-one, short reaction times, environmentally benign, recoverability of the catalyst and reusability without significant loss of its catalytic performance.

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.

Anti-MRSA (Multidrug resistant Staphylococcus aureus) activity of 3-substituted coumarins

Background: Infectious pathogenic bacteria are the key virulence in our daily life. Especially diseases produced by multidrug resistant Staphylococcus aureus (MRSA) still contributing in morbidity and mortality in humans. Discovery of new and safer antibi

Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?

Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumari