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Relevant academic research and scientific papers

Syntheses and evaluation of daphnetin derivatives as novel G protein-coupled receptor inhibitors and activators

A series of daphnetin (7,8-dihydroxycoumarin) derivatives 1–22 were synthesized including sixteen new compounds (1–5, 7–14, 18, 21 and 22) and six known compounds (6, 15–17, 19 and 20). Their pharmacological activities on G protein-coupled receptors (GPCRs) were evaluated by double antibody sandwich ELISA (DAS-ELISA) in vitro. Daphnetin derivatives with various substitution patterns/groups were obtained from inhibitors to activators on GPCRs. Derivatives 2–5, 8, 15, 16 and 18–20 possessed moderate activation potency on GPCRs. Among them, derivatives 3–5, 16 and 19 presented significant activation potency on GPCRs with EC50 values in the range of 1.18–1.91 nM. Derivatives 6, 11, 14 and 18 showed significant inhibitory potency on GPCRs with IC50 values in the range of 1.26–1.38 nM. Moreover, the structure-activity relationships (SARs) of daphnetin derivatives were discussed in detail. The new daphnetic-based GPCRs activators and inhibitors have potentials as future drug candidates for the treatment of metabolic diseases.

Inhibitor daphnetin derivative and application and pharmaceutical composition thereof

The invention provides an inhibitor daphnetin derivative and application and a pharmaceutical composition thereof. The daphnetin derivative (1-13) or the pharmaceutically acceptable salt or solvent compound thereof is shown as the following formula. The p

Introduction of poly(4-vinylpyridinium) perchlorate as a new, efficient, and versatile solid acid catalyst for one-pot synthesis of substituted coumarins under ultrasonic irradiation

Poly(4-vinylpyridinium) perchlorate, is a supported, recyclable, eco-benign catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. The catalyst was studied by FT-IR, X-ray diffraction, scanning electron microscope, thermo-gravimetric and energy dispersion X-ray analyses. All the products were extensively characterized by 1H NMR, FT-IR, MS and melting point analyses. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times without loss of activity.

Ultrasound-assisted one-pot synthesis of substituted coumarins catalyzed by poly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst

Poly(4-vinylpyridinium) hydrogen sulfate solid acid was found to be efficient catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times.

Succinimide-N-sulfonic acid catalyzed synthesis of bis(indolyl)methane and coumarin derivatives under mild conditions

A mild and simple procedure is described for the synthesis of bis(indolyl)methane and coumarin derivatives using succinimide-N-sulfonic acid as an efficient, cheap, and reusable catalyst under mild conditions.

Ultrasound-assisted Pechmann condensation of phenols with β-ketoesters to form coumarins, in the presence of bismuth(III) chloride catalyst

Ultrasound was found to synergistically accelerate the condensation of phenol with β-ketoesters in the presence of BiCl3. In the absence of ultrasound, under the same conditions, the reaction was found to be slow. Thus, the reaction can be carried out in the presence of ultrasound at room temperature (28-30°C), with a considerable reduction of reaction time, with high yield and high purity of coumarins. Copyright Taylor & Francis Group, LLC.

A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst

Seventeen examples are resolved, most of them in good to excellent yields, using the cheap WD catalyst. Substituted coumarins are synthesized from phenols and β-ketoesters by the Pechmann reaction, using a Wells-Dawson heteropolyacid (H6P2W18O62? 24H2O) as catalyst by a solvent-free procedure. This one requires low reaction times, 130°C temperature and as little as 1 mol % of Wells-Dawson acid, obtaining good to excellent yields of coumarins. The catalyst showed to be reusable with no differences in the yields. The results are compared with those of the reactions performed in toluene solution. The presented synthetic procedure is a convenient, clean and fast alternative for synthesizing 4-substituted coumarins (17 examples).

Synthesis of coumarin by Yb(OTf)3 catalyzed Pechmann reaction under the solvent-free conditions

Yb(OTf)3 is used as an alternative to conventional acid catalysts in the Pechmann condensation reaction of phenols with β-keto esters leading to the formation of coumarin derivatives. This new method has the advantage of high yields, solvent-free conditions, short reaction times and reusability of the catalyst with no loss of yield. Ytterbium triflate catalyzed Pechmann reaction applied to synthesis of coumarin derivatives is simple and environmentally friendly process.

Synthesis of coumarins catalyzed by eco-friendly W/ZrO2 solid acid catalyst

Synthesis of substituted coumarins via reactions of resorcinol and substituted resorcinol with ethyl acetoacetate and ethyl α-methylacetoacetate (Pechmann reaction) are reported, in which the production of environmentally harmful waste streams is minimized by the use of a novel solid acid catalyst.