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Furan-2-carboxylic acid, a natural product isolated and purified from the herbs of Hexagonia speciosa with anti-bacterial effect, is also an orally active selective human cathepsin K inhibitor which may have the therapeutic potential for the treatment of diseases characterized by excessive bone loss including osteoporosis.
Synonyms: Furan-2-carboxylic acid; Pyromucic acid; Kyselina 2-furoova
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Furan-2-carboxylic acid, a natural product isolated and purified from the herbs of Hexagonia speciosa with anti-bacterial effect, is also an orally active selective human cathepsin K inhibitor which may have the therapeutic potential for the treatment of diseases characterized by excessive bone loss including osteoporosis.
Synonyms: Furan-2-carboxylic acid; Pyromucic acid; Kyselina 2-furoova
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*For Research Use Only !
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Xue, Qiang ; Li, Hanxi ; Jin, Peng ; Zhou, Xukai ; Wang, Feng ;
Abstract: Traditional H2O2 photocatalysis primarily depends on photoexcited electrons and holes to drive oxygen reduction and water oxidation, respectively. However, singlet oxygen (1O2), often underappreciated, plays a pivotal role in H2O2 production. Meanwhile, photocatalytic biomass conversion has attracted attention, yet studies combining H2O2 synthesis with biomass valorization remain rare and typically yield low-value products. Herein, we report a strategy of photocatalytic valorization of furfuryl alcohol (FFA) coupled with the efficient co-production of H2O2, enabled by covalent organic frameworks (COFs) induced, 1O2-participated Achmatowicz rearrangement. This study introduces polyimide-based COF-N0-3 with tailored nitrogen content, representing an unprecedently efficient platform for 1O2 production. Remarkably, reducing the nitrogen content of the COF enhances 1O2 production, significantly boosting the H2O2 generation rate. In FFA, the primary pathway for H2O2 production is Achmatowicz rearrangement, achieving a rate ten times higher than that reliant on oxygen reduction reaction in pure water, reaching 4549 μmol g -1 h -1. Mechanism studies revealed 1O2 selectively engaged FFA, bypassing hole oxidation to trigger the Achmatowicz rearrangement, producing valuable 6-hydroxy-(2H)-pyranone with 99% conversion and 92% selectivity. This work establishes a coupling strategy for simultaneoues synthesis of H2O2 and biochemicals, offering a transformative approach to sustainable photocatalysis.
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Keywords: covalent organic frameworks ; hydrogen peroxide photosynthesis ; biomass valorization coupling ; singlet oxygen
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Purchased from AmBeed: 88-14-2 ; 35436-57-8
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CAS No. : | 88-14-2 |
Formula : | C5H4O3 |
M.W : | 112.08 |
SMILES Code : | O=C(C1=CC=CO1)O |
Synonyms : |
Furan-2-carboxylic acid; Pyromucic acid; Kyselina 2-furoova
|
MDL No. : | MFCD00003238 |
InChI Key : | SMNDYUVBFMFKNZ-UHFFFAOYSA-N |
Pubchem ID : | 6919 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride; In chlorobenzene; at 35 - 80℃; for 24h;Catalytic behavior; | In a 250ml four-necked bottle, add 20g of furoic acid, 23.2g of anisole, 100ml chlorobenzene, stirred and mixed; oil bath heated to internal temperature 35 ~ 40 C, slowly added 55.9g anhydrous aluminum trichloride; after the completion of the feed, stirring at 75-80 C for about 24 hours; cooling, concentrated distillation under reduced pressure Chlorobenzene After the distillation was completed, the temperature was lowered to room temperature, 60 ml of N,N-dimethylformamide was added to the reaction flask, and the mixture was stirred and mixed. At room temperature, 32.1 g of anhydrous aluminum trichloride was slowly and separately added; after the completion of the feeding, the oil bath was heated to The internal temperature is 135 C, and the reaction is kept for 6 hours; The water is cooled to room temperature; the reaction solution is slowly added to dilute hydrochloric acid solution for hydrolysis; extracted with ethyl acetate several times, and the ethyl acetate extract is combined, washed with water, and Ph is weakly acidic; The organic layer was concentrated under reduced pressure to recover ethyl acetate; The residue is decolorized and recrystallized with dilute alcohol water. Yielding 19.7 g of 6-hydroxy-1-naphthoic acid as a gray to pale yellow powder. Yield: 58.7%, melting point: 205.5 to 208.6 C, purity: 98.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: To a solution of acid 1 (1.0g, 8.9 mmol) in THF (15 mL) was added Et3N (3.1 mL, 22.2 mmol), and T3P (50% solution in EtOAc, 10.6mL, 17.7 mmol) at 0-5 C and the solution was stirred for about 10 min under a nitrogen atmosphere. Then N,O-dimethylhydroxylaminehydrochloride salt (1.1g, 13.3 mmol) was added to the reaction mixture at 0-5 C and the heterogeneous mixture was allowed to stir at room temperature till the completion of the reactionas indicated by TLC (see Table S-1). The mixture was then diluted with water(20 mL) followed by ethyl acetate (20 mL) and stirred for about 10 min. The separated organic layer was collected, washed with 5% citric acid (2 x10 mL),5% Na2CO3 (2 x 10 mL), and then brine solution. The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated under low vacuum. The crude product obtainedwas purified by flash column chromatography over silicagel (100-200 mesh) using 12-15% EtOAc / n-hexane as eluent to affordthe desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compounds 41-70 were part of a parallel set prepared in library plate format according to General Procedure L, outlined below. ; L. General Procedure for Plate Preparation-Amide Formation XXI: Resin bound deprotected biarylphenol XVII (prepared from intermediate XII, boronates XIVd and XIVe, following general procedures D-F) was distributed into a 96 well plate, 10 mg of resin (0.013 mmol) per well. To the resin 400 mul of dichloromethane was added, followed by 100 mul of DIEA, followed by 0.13 mmol (10 equiv) of heterocyclic carboxylic acid XXa-XXn was added followed by 61 mg (0.13 mmol, 10 equiv) of PyBrop. The plate was shaken at room temperature for 24 hours, then drained and washed with dichloromethane, methanol/dichloromethane, dimethylformamide, methanol/dichloromethane and dichloromethane. The compounds were cleaved with TFA/dichloromethane (600 mul, 1:1) into a 96 deep well plate and submitted for testing without further purification. (Mass spec results obtained are shown in Table 4). Carboxylic Acids Het-COOH XX: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.93 g (17.4 mmol, 69.6%) | With hydrogenchloride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; | Example 141 Synthesis of Compound 141 In 100 mL of methanol, was dissolved 5.90 g (50.0 mmol) of monomethyl malonate, and the resulting solution was mixed with 2.86 g (25 mmol) of magnesium ethoxide followed by stirring at room temperature for 4 hours. The reaction solution was concentrated and the residue was dried under reduced pressure. In 100 mL of tetrahydrofuran, was dissolved 2.80 g (25 mmol) of 2-furancarboxylic acid and the resulting solution was mixed with 4.45 g (27.4 mmol) of carbonyldiimidazole, followed by stirring for 1 hour. The reaction solution was added to a dry magnesium salt and stirred at room temperature for 19 hours. The reaction solution was concentrated; the residue was mixed with 100 mL of 1.5 N hydrochloric acid, extracted with ethyl acetate, and washed with an aqueous sodium hydrogencarbonate solution and saturated sodium chloride water. The resultant was dried over sodium sulfate anhydride, filtered, and concentrated. The residue was distilled (0.06 mmHg, 69 to 75) to give 2.93 g (17.4 mmol, 69.6%) of methyl 2-furancarbonylacetate as an anhydrous liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%). |
Tags: 2-Furoic acid | COX | Others | Natural Products-Other Structure | ATP Citrate Lyase | ACAT | Endogenous Metabolite | Tumor Development and Microenvironment Evolution | Biological Buffers | Fluorescence Labeling Reagents | Metabolic Enzyme | Immunology/Inflammation | Tumor Metabolism | By Structure | Steroids | Fluorescent Dyes | Other Inhibitors/Agonists | Small Molecule Positive Drugs | Structure | 88-14-2
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