51786-56-2

Upstream product

• 504-15-4 orcinol 
• 105-45-3 acetoacetic acid methyl ester 
• 5396-89-4 benzyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 75-77-4 chloro-trimethyl-silane 
• 141-97-9 ethyl acetoacetate 
• 64-19-7 acetic acid 

Downstream Products

• 703-29-7 1-(2,4-dihydroxy-6-methylphenyl)ethanone 
• 182954-12-7 7-hydroxy-4,5-dimethyl-8-nitrosocoumarin 
• 1637476-92-6 4,5-dimethyl-2-oxo-2H-1-benzopyran-7-yl phenylcarbamate 

Relevant academic research and scientific papers

Microwave-assisted Pechmann reaction on P2O5/molecular sieves. Application to the preparation of 4-substituted coumarins

4-Substituted coumarins were efficiently and rapidly synthesised via Pechmann condensation of phenols with ethyl acetoacetate catalyzed by P2O5/molecular sieves in satisfactory yields.

Synthesis, computational studies and antiproliferative activities of coumarin-tagged 1,3,4-oxadiazole conjugates against MDA-MB-231 and MCF-7 human breast cancer cells

A novel library of coumarin tagged 1,3,4 oxadiazole conjugates was synthesized and evaluated for their antiproliferative activities against MDA-MB-231 and MCF-7 breast cancer cell lines. The evaluation studies revealed that compound 9d was the most potent molecule with an IC50 value of 50 = 7.07 μM), in Estrogen Negative (ER?) cells than Estrogen Positive (ER+) cells. Structure–activity relationship (SAR) studies revealed that conjugates bearing benzyl moieties (9b, 9c and 9d) had superior activities compared to their alkyl analogues. The most potent compound 9d showed ～1.4 times more potent activity than tamoxifen against MCF-7 cell line; while the introduction of sulfone unit in compounds 11a, 11b and 11c resulted in significant cytotoxicity against both MCF-7 and MDA-MB-231 cell lines. These results were further supported by docking studies, which revealed that the stronger binding affinity of the synthesized conjugates is due to the presence of sulfone unit attached to the substituted benzyl moiety in their pharmacophores.

B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions

Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]

Synthesis of coumarin derivatives in a microfluidic flow system employing the Pechmann condensation: A case study

For the synthesis of coumarin derivatives using the Pechmann condensation scheme, an acidic ionic liquid catalyst, abbreviated as [EBsImH][HSO4], was prepared from the ring opening of 1,4-butanesultone by 1-ethylimidazole, followed by the addition of 1 equiv. H2SO4(c). The [EBsImH][HSO4]-catalyzed Pechmann condensation reactions proceeded smoothly in a batch setup, with recyclable [EBsImH][HSO4] showing great catalytic activity. The acidic ionic liquid catalyst [EBsImH][HSO4] was recovered from EtOAc/H2O extraction of the product mixture, where the H2O layer was worked up and dried for reuse in consecutive runs of the Pechmann condensation reactions, maintaining >85% conversion for four times. The catalytic reactions were also carried out in a microfluidic flow setup. The flow parameters, the reactant molar amounts, and the additional H2SO4 as a modifying acid catalyst were optimized in the current case study. A minimum conversion rate of 2.8 g/hr of coumarin derivatives was demonstrated.

Synthesis, Cytotoxicity and Antimicrobial Evaluation of New Coumarin-Tagged β-Lactam Triazole Hybrid

A series of coumarin-tagged β-lactam triazole hybrids (10a–10o) were synthesized and tested for their cytotoxic activity against MDA-MB-231 (triple negative breast cancer), MCF-7 (estrogen receptor positive breast cancer (ER+)) and A549 (human lung carcinoma) cancer cell lines including one normal cell line, HEK-293 (human embryonic kidney). Two compounds 10b and 10d exhibited substantial cytotoxic effect against MCF-7 cancer cell lines with IC50 values of 53.55 and 58.62 μm, respectively. More importantly, compounds 10b and 10d were non-cytotoxic against HEK-293 cell lines. Structure–activity relationship (SAR) studies suggested that the nitro and chloro group at the C-3 position of phenyl ring are favorable for anticancer activity, particularly against MCF-7 cell lines. Furthermore, antimicrobial evaluation of these compounds revealed modest inhibition of examined pathogenic strains with compounds 10c and 10i being the most promising antimicrobial agents against Pseudomonas aeruginosa and Candida albicans, respectively.

N-Doped Carbon Wrapped Polyoxometalate Derived from POM-IL Hybrid: A Heterogeneous Catalyst for the Synthesis of Coumarin Derivatives under Solvent-Free Conditions

Vanadium substituted Keggin type polyoxometalate loaded N-doped carbon was prepared from polyoxometalate ionic liquid hybrid by carbonization process. The decomposition of organic part generates various functional groups leaving polyoxometalate part intact. The catalyst was characterized by elemental analysis, FTIR, MAS 13C NMR, XPS and electron microscopy studies. The presence of carboxylic acids, aromatic and hetero-aromatic groups in the catalyst was confirmed by 13C NMR. The high resolution C1s and O1s XPS analysis further confirmed the presence of these groups. Various oxidation states of nitrogen were confirmed by deconvoluted N1s XPS spectra. Pyridine adsorption study confirms the presence of Bronsted and Lewis acid sites in the catalyst. Layered structure of the catalyst was confirmed by HR TEM analysis. The hybrid material displayed excellent catalytic activity towards the synthesis of coumarin derivatives under solvent-free conditions.

Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation

2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.

α-Glucosidase Inhibition, Antioxidant and Docking Studies of Hydroxycoumarins and their Mono and Bis O-alkylated/acetylated Analogs

Background: Diabetes Mellitus (DM) is a complex metabolic disease illustrated by abnormally high levels of plasma glucose or hyperglycaemia. Accordingly, several α-glucosidase inhibitors have been developed for the treatment of diabetes and other degenerative disorders. While, a coumarin ring has the privilege to represent numerous natural and synthetic compounds with a wide spectrum of biological activities e.g. anti-cancer, anti-HIV, anti-viral, anti-malarial, anti-microbial, anti-convulsant, anti-hypertensive properties. Besides this, coumarins have also shown potential to inhibit α-glucosidase leading to a generation of new promising antidiabetic agents. However, the testing of O-substituted coumarins for α-glucosidase inhibition has evaded the attention of medicinal chemists. Methods: For O-alkylation/acetylation reactions, the hydroxyl coumarins (A-B) initially activated by K2 CO3 in dry DMF were reacted with variedly substituted haloalkanes at room temperature under nitrogen. The synthesized compounds were tested for their α-glucosidase (from Saccharomyces cerevisiae) inhibitory activity and anti-oxidant activity using DPPH radical scavenging activity. In silico docking simulations were conducted using CDocker module in DS (Accelrys) to explore the binding modes of the representative compounds in the catalytic site of α-glucosidase. Results: All the coumarin analogues (A1, B1, A2-A10, B2-B8) including their precursors (A-B) were evaluated for their in vitro α-glucosidase inhibition using acarbose as a standard inhibitor. All the mono O-alkylated coumarins (except A1) showed significant (p 50 values ranging between 11.084±0.117 to 145.24± 29.22 μg/mL. Compound 7-(benzyloxy)-4, 5-dimethyl-2H-chromen-2-one (A9) bearing a benzyl group (Ph-CH2 -) at position 7 showed a remarkable (p 50 = 11.084±0.117 μg/mL), almost four-fold more than acarbose (IC50 = 40.578±5.999 μg/mL). The introduction of –NO2 group dramatically improved the anti-oxidant activity of coumarin, while the O-alkylation/acetylation decreased the activity. Conclusion: The present study describes the synthesis of functionalized coumarins and their evaluation for α-glucosidase inhibition and antioxidant activity under in vitro conditions. Based on IC50 data, the mono O-alkylated coumarins were observed to be stronger inhibitors of α-glucosidase with respect to their bis O-alkylated analogues. Coumarin (A9) bearing O-benzyloxy group displayed the strongest α-glucosidase inhibition, even higher than the standard inhibitor acarbose. The coumarin (A10) bearing –NO2 group showed the highest anti-oxidant activity amongst the synthesized compounds, almost comparable to the ascorbic acid. Finally, in silico docking simulations revealed the role of hydrogen bonding and hydrophobic forces in locking the compounds in catalytic site of α-glucosidase.

Synthesis method of coumarin compounds

The invention relates to a synthesis method of coumarin compounds. The method particularly comprises the following steps: performing reaction for 40 to 120 minutes by taking substituted phenol and beta-keto ester as substrates and DES as a catalyst under the condition of no solvents and at the temperature of 50 to 100 DEG C to prepare the coumarin compounds. In the preparation process of the coumarin compounds, other organic solvents do not need to be added and the DES serves as a reaction catalyst and solvent. The DES can be reused and is environment-friendly, and the catalytic effect basically maintains unchanged after the DES is recovered for four times. The preparation method provided by the invention is simple in process, high in catalytic activity and high in yield; and after reaction, treatment is simple, convenient and environment-friendly.

7 - aryloxyacetic acetyloxy coumarin compound and its application in pesticide (by machine translation)

The invention provides a 7 - aryloxyacetic acetyloxy coumarin compound and its application in pesticide, preparation are as follows: 1, will contain different substituents of the resorcinol add to the reaction bottle of the concentrated sulfuric acid, stirring and dissolving, ice water bath cooling slowly dripping acetoacetate compound, then completing, ice water bath cooling under reaction 1h; reacting at room temperature 24h; violent stirring into ice water in the mixture, a yellow precipitation, filtered, the filter cake is anhydrous ethanol recrystallize to get 7 - hydroxy coumarin compound; 2, 2, 4 - dichloro acid with oxalyl dissolved in CH2 Cl2 In the solvent, dropping N, N - dimethyl formamide, room temperature reaction 2h make acyl chloride; 3, containing 7 - hydroxy coumarin compounds and acyl chloride in the organic solvent, under a certain temperature, adding catalyst, reaction after a period of time, re-crystallization to obtain the 7 - aryloxyacetic acetyloxy coumarin compound. The compounds of the invention have very high herbicidal activity. (by machine translation)