48 results about "4-Hydroxycoumarins" patented technology

The invention discloses a novel compound 3,3'-(3,4-dichlorobenzylidene)-bis-4-hydroxycoumarin with a strong antibacterial effect which is optimized by transforming the structure of bishydroxycoumarin compounds, and provides a preparation method thereof, wherein the chemical structure and crystal structure are obtained. The novel compound 3,3'-(3,4-dichlorobenzylidene)-bis-4-hydroxycoumarin has an antibacterial application value in preparation of a medicine resisting staphylococcus aureus (ATCC29213), methicillin-resistant staphylococcus aureus (MRSA, XJ7502), USA300 (LAC) and vancomycin-resistant staphylococcus aureus (Mu20ATCC700699).

Provided herein are methods for the biosynthesis of 4-hydroxycoumarin. In one embodiment, provided herein are genetically engineered microbes that include a metabolic pathway for the production of 4-hydroxycoumarin. Also provided are methods for using the genetically engineered microbes to produce 4-hydroxycoumarin, and using the 4-hydroxycoumarin as the starting point for the synthesis of other compounds.

A process for the preparation of 1,2-benzisoxazole-3-methane-sulfonamide without isolation of intermediates in solid form, by using 4-hydroxycoumarin as a starting compound, and water and 1,2-dichloro-ethane as solvents; and an industrially useful process for the preparation of 1,2-benzisoxazole-3-acetic acid, by reacting 4-hydroxycoumarin and hydroxylamine in water.

The invention discloses a method for catalytically preparing a 4,5-dihydropyran[c]chromene derivative, and belongs to the technical field of chemical material preparation.In the preparation reaction, the molar ratio of aromatic aldehyde to 4-hydroxycoumarin to malononitrile is 1:1:(1-1.2), the molar weight of an alkaline ionic liquid catalyst is 8%-15% of that of aromatic aldehyde, the volume dose of a 50% ethanol water solution serving as reaction solvent on a milliliter basis is 8-10 times of the molar weight of aromatic aldehyde on a millimole basis, the reflux reaction time ranges from 10 min to 28 min, after the reaction is finished, cooling is conducted to room temperature, extraction filtration is conducted, filter residues are washed with ethyl alcohol and vacuum-dried, and the 4,5-dihydropyran[c]chromene derivative is obtained.Compared with a preparation method adopting other alkaline ionic liquid catalysts, the method for catalytically preparing the 4,5-dihydropyran[c]chromene derivative has the advantages of being high in catalytic activity of the catalyst, free of treatment during the reuse process, high in raw material utilization rate, easy and convenient to operate in the whole preparation process and the like, and large-scale industrial application is convenient.

The invention relates to an additive of weed killer, wherein it is formed by 0.01-5% 4-hydroxycoumarin and 95-99.99% abies. The inventive additive can be used with weed killer, to accelerate the decomposition of left weed killer, and improve the effect of killer. The invention can eliminate bad root, low growth, etc. And the tests have proved its effect.

A specific technique of a method of synthesizing 4-hydroxycoumarin and derivatives of 4-hydroxycoumarin is as follows: taking a phenol or the derivatives of the phenol and an Meldrum's acid as the raw materials, using a thin layer method to monitor and then decompressing to remove an acetone after complete reaction; with no necessity of separating an intermediate product, directly carrying out intermolecular dehydration with an ito agent or a polyphosphoric and ring-closing reaction and finally adding water to precipitate a sedimentation, filtrating and then recrystallizing to get a final product---4-hydroxycoumarin and the derivatives of 4-hydroxycoumarin. The proportion of the phenol, the derivatives of the phenol, the Meldrum's acid, the ito agent or the polyphosphoric is 1.0mmol:1.0mmol:1-3ml or 1 to 2g. The temperature of intermolecular ring-closing reaction when adding the ito agent is 60 DEG C to 70 DEG C; the reaction time is 1 to 5 hours. The temperature of intermolecular ring-closing reaction when adding the polyphosphoric is 110 DEG C to 120DEG C; the reaction time is 3 to 7 hours. The method has the advantages of easy raw material obtaining, mild reaction condition, simple operation condition and less pollution. Furthermore, the yield varies from medium to excellence; no catalyst is needed; the method also assures a high yield ratio.

The invention provides a 4-hydroxycoumarin-containing cadmium-inserted fluorescent material and a synthesis method thereof, and relates to the field of fluorescent materials. The 4-hydroxycoumarin-containing cadmium-inserted fluorescent material has a molecular formula of {[Cd(4,4'-bpp)2(H2O)2].2(4-Hcm-).H2O}n, is a light yellow crystal, is synthesized by a solution method and has high purity. At a room temperature, the {[Cd(4,4'-bpp)2(H2O)2].2(4-Hcm-).H2O}n produces bright blue-fluorescence under the irradiation of ultraviolet rays, and has a quantum yield of 12% and strength obviously higher than strength of dissociative fluorescent molecules and a main metal organic framework. The synthesis method is a novel method, has simple processes, low equipment requirements and a low cost. The 4-hydroxycoumarin-containing cadmium-inserted fluorescent material is in a crystal state, has high purity, good heat stability and good regulation performances, can be used as a novel fluorescent material and can be used for manufacture of a fluorescent luminescent device.

The invention discloses a 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton, and a synthesis method and an application thereof. The structural formula of the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton is shown in the description; and in the structural formula, R<1> is any one of a methyl group and an ethyl group, R<2> is one of the hydrogen atom, a methylgroup and halogens, and R<3> is any one of the hydrogen atom and the halogens. The synthesis method of the bioactive skeleton comprises the following steps: mixing an ortho-aminobenzaldehyde compoundwith a 4-hydroxycoumarin compound in a solvent according to a molar ratio of 1:(1-2), and performing a reaction at 70-90 DEG C to obtain the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone compound. The synthesis method is a method for efficiently synthesizing the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone compound in the green ethanol solvent by the one-step reaction without using a catalyst, and realizes a hydrogen transfer reaction in which the natural product molecule 4-hydroxycoumarin participating for the first time in order to synthesize the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone compound.

The invention provides a phosphate salt plant growth conditioning agent, which comprises the following components by weight percentage: potassium 5-nitro guaiacol phosphate 0.1-98%, potassium o nitrophenol phosphate 0-97%, potassium p nitrophenol phosphate 0-97%, potassium 2,4-dinitrophenol phosphate 0-97%, potassium 4-hydroxycoumarin phosphate 0-97% and potassium triacontanol phosphate 0-97%. The plant-growth regulator can be used for agriculture and forestry production by soaking seed, dressing seed or sprinkling leaf, and has the effects for promoting rooting, accelerating maturation, increasing yield and alleviating drug damage with convenient usage, safety and other characteristics.

The invention discloses a high performance rodenticide composed of 3-p-bromobiphenyl-1, 2, 3, 4-tetralol, pinellia ternate and 4-hydroxycoumarin. The rodenticide of the invention has reasonable formula, good using effect and low production cost.

The invention discloses ionic liquid-promoted one-pot method for synthesizing 4H-pyranocoumarin derivatives. The method comprises the steps of performing a reaction under stirring for 0.5-12 h by using 4-hydroxycoumarin, one aromatic aldehyde compound and malononitrile as reaction substrates and a functionalized ionic liquid as a catalyst at room temperature to obtain one target product 4H-pyranocoumarin derivative. According to the method provided by the invention, the ionic liquid catalyst used in the method is simple and convenient to prepare, and the raw materials have good biocompatibility, and are cheap and easy to obtain; the one-pot method for preparing the 4H-pyranocoumarin derivatives has mild reaction conditions, does not need to add auxiliary agents such as a solvent, and has high atomic economy; the reaction system is non-corrosive to equipment, and has no special requirements for a reactor; the operation and post-treatment process of the catalytic system are simple, and the ionic liquid catalyst can be conveniently recycled; therefore, the method is a preferred method for industrial synthesis of the 4H-pyranocoumarin derivatives.

The invention relates to a pyran[2,3-b] quinoline derivative as well as a synthesis process and application thereof in tumor prevention. According to the synthesis process, multiple components are adopted to react, namely, a compound of chemical formula II, malononitrile and 4-hydroxycoumarin as raw materials, are subjected to three-component reactions in the presence of a solvent under catalysisof a solvent and the microwave radiation, then a target compound is synthesized at one step, that is, the pyran[2,3-b] quinoline derivative (formula I). The pyran[2,3-b] quinoline derivative has the advantages that multi-component reactions are carried out in the synthesis process, the pyran[2,3-b] quinoline derivative is synthesized from the three raw materials by using a 'one pot boiling' method, the derivative is a quite stable compound, and the compound has a relatively good in-vitro propagation inhibition function on a human liver tumor cell system HepG2.

The invention relates to an herbicide composition for sorghum fields and coix seed fields. The composition has active ingredients, which comprise three substances including atrazine, quinclorac and bentazone; 4-hydroxycoumarin is used as a safener. The herbicide composition is suitable for post-seedling weeding in sorghum fields and coix seed fields, and can effectively control herbicide-resistant barnyard grass in sorghum fields and coix seed fields, Setaria glauca, Leptochloa panacea, Digitaria ischaemum, Cyperus iria and dandelion. The herbicide composition is very safe for sorghum and coix seeds, and has enormous economic benefits and social benefits.

The invention discloses preparation and applications of a 4-hydroxycoumarin compound. The 4-hydroxycoumarin compound is prepared through following steps: under nitrogen gas protection, 2.0mmol of 4-hydroxycoumarin, 2.0mmol of a fenamic acid non-steroidal anti-inflammatory drug (mefenamic acid, flufenamic acid, and tolfenamic acid), and 2.4mmol of 1-ethyl-(3-dimethyllaminopropyl)carbodiie hydrochlide (EDCI.HCl) are mixed, 0.2mmol of a dimethylaminopyridine solution is added slowly dropwise as a catalyst, and room temperature reaction is carried out for 2h, after condensation, a silica gel column is adopted for purifying so as to obtain a finished product. The 4-hydroxycoumarin compound can be used in preparation of neuroinflammation inhibitors and drugs used for treating senile dementia.

The invention provides a fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2, and the fluorescent probe is called Co-SO2 for short. The fluorescent probe has a structure asshown in a formula (I) which is shown in the description. A synthesis method of the fluorescent probe comprises the following steps: (1) heating 7-diethylamino-4-hydroxycoumarin and POCl3 in DMF (Dimethyl Formamide) for reacting, and separating and purifying, thus obtaining the fluorescent probe. The Co-SO2 fluorescent probe provided by the invention is a simple, fast and sensitive GSH, SO2 and Cys distinguishing reagent; the fluorescent probe can specifically react with GSH, SO2 and Cys under low concentration, and is capable of resisting interference of various active oxygen, amino acid andsulfydryl-containing compounds.

The invention discloses preparation and application of 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst. P-methoxyaniline and paraformaldehyde are taken as raw materials and are subjected to reaction including hydrolysis, Mannich and the like to synthesize the 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst base derivative; the compound is taken as catalyst tocatalyze addition reaction taking 4-hydroxycoumarin and benzyl cyanide as raw materials, and one series of pyranoid ring derivative is synthesized. According to the invention, the substrate range of the pyranoid ring derivative is widened, and the application range of TB on the aspect of catalysis is widened.

The invention discloses a method for distinguishing 4-hydroxycoumarin (4-HC) and isomer 7-hydroxycoumarin (7-HC) thereof, which is characterized in that a nonlinear chemical oscillation system of H2SO4-NaBrO3- [CuL] (ClO4) 2-malic acid is used as a distinguishing solution, according to the different influences of 4-hydroxycoumarin (4-HC) and isomer 7-hydroxycoumarin (7-HC) thereof on the oscillation spectrum peak shape of the oscillation system, thereby realizing the differentiation of 4-hydroxycoumarin (4-HC) and the isomer 7-hydroxycoumarin (7-HC) thereof. The potential oscillation spectrumprovided by the invention has intuition, can conveniently and quickly distinguish 4-hydroxycoumarin (4-HC) and the isomer 7-hydroxycoumarin (7-HC) thereof, and the device is simple, has high accuracyand is easy to operate and observe.

The invention relates to a preparation method of chiral warfarin and chiral warfarin derivatives. The invention aims to provide a preparation method which is simple to operate, has low cost and is is suitable for industrial production. The preparation method comprises the following steps: 1) performing alcohol-aldehyde reaction in a mixed solvent of ethanol and water, wherein the volume ration ofethanol to water in the mixed solvent is 5:2-3 and the dosing molar ratio of substituted benzaldehyde to acetone is 1:2; the aqueous solution is maintained to be alkaline in the reaction process; after the reaction, the product is separated and purified to obtain light yellow solid which is the intermediate product substituted benzalacetone; and 2) in the reaction solvent, performing 1,4-additionreaction between the substituted benzalacetone and 4-hydroxycoumarin under the joint action of chiral catalyst, acetic acid and auxiliary catalyst, wherein the dosing molar ratio of substituted substituted benzalacetone to 4-hydroxycoumarin is 1:1.5-1.6, and the acetic acid is 1-10 times as much as 4-hydroxycoumarin; adjusting the pH value to 7 after the reaction to obtain the chiral warfarin andderivative products of the chiral warfarin.

The invention discloses 3,3'-(3,5-difluorobenzylidene)-bis-4-hydroxycoumarin and application thereof. According to the invention, 3,3'-(3,4-dichlorobenzylidene)-bis-4-hydroxycoumarin is prepared and is found to have good in-vitro and in-vivo activity and exert strong inhibitory effect on leukemia tumor cells; and 3,3'-(3,4-dichlorobenzylidene)-bis-4-hydroxycoumarin is low in toxicity and good in safety.

The invention relates to the technical field of medical treatment. Theanine is a characteristic amino acid of tea, can be used for inhibiting cell growth and invasion of human pancreatic cancer, cervical cancer, gastric cancer, breast cancer and other cancers as well as remarkably inhibiting growth of tumors in a body, and has an inhibition effect superior to anti-cancer medicines such as cyclophosphamide. The action mechanism relates to down-regulation of receptors closely related to inhibition of tumor growth, invasion and transfer, signal transduction regulated protein, kinase level and combination of nuclear factors and DNA, as well as upper regulation of factors such as cancer-inhibiting protein and cell cycle inhibition protein; and the theanine can be used for directly inhibiting the activity of histone deacetylase and histone methyltransferase EZH2 and combination of inflammatory factor NF-kappa B and DNA. Furthermore, the theanine can be synergized with 6-fluoro-4-hydroxycoumarin (X) to improve inhibition on tumor cell growth and invasion by times, and has the activity superior to that of cyclophosphamide and the like. The theanine and synthesis with X can be applied to prevention and treatment of tumors, inflammations, cardiovascular diseases, immunodeficiency and other diseases.

The invention relates to an additive of weed killer, wherein it is formed by 0.01-5% 4-hydroxycoumarin and 95-99.99% abies. The inventive additive can be used with weed killer, to accelerate the decomposition of left weed killer, and improve the effect of killer. The invention can eliminate bad root, low growth, etc. And the tests have proved its effect.

The invention relates to a preparation method of tecarfarin. The method comprises the steps of adopting formylbenzoic acid and 4-hydroxycoumarin as substrates, carrying out addition reaction, and condensing with 1,1,1,3,3,3-hexafluoro-tert-butanol to obtain the end product tecarfarin. According to the method, esterolysis impurities caused by condensation reaction carried out at high temperature in the prior art is avoided, the purity and the yield are greatly improved, and the method is simple to operate, convenient to post-process, and suitable for industrial production.

The invention provides a new Tecarfarin preparation method, which comprises: carrying out acyl chlorination on 4-carboxybenzaldehyde, carrying out condensation with 1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol to form an ester, and carrying out a reaction on the obtained ester intermediate and 4-hydroxycoumarin under the catalysis of proline and under a alkyl 2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate reducing condition to prepare the target product Tecarfarin. According to the present invention, the method has advantages of high controllability of each reaction, mild reaction condition,simple post-treatment, significantly improved yield of the target product, and good industrial application prospects; and with the method, the starting raw material has characteristics of easy obtaining and low price so as to substantially reduce the whole production cost.

The invention discloses a 3-(2-furan)-4-hydroxycoumarin compound, preparation method thereof and application of anti-plant fungus. The formula is shown in description, wherein R1, R2, R3 and R4 independently represent any of H, methyl, methoxy, ethoxy, fluorine, chlorine and bromine, 3-(2- Hydroxyphenyl)-3-Oxopropanoate ester compounds, K10 montmorillonite and 2.5-Dimethoxy-2.5-dihydrofuran is heated and subjected to coupling reaction, sodium hydroxide is added, and refluxed in ethanol solution, followed by separation and purification, the pure product of the compound is obtained. The synthesis method has the advantages of no solvent, cheap raw materials and K10 montmorillonite catalysis, simple and convenient process, simple operation, high product yield, low production cost and the like,and the obtained compound has good anti-plant fungal effect and can be developed into a novel pesticide with anti-plant fungi.

The invention relates to the field of organic synthesis and particularly relates to a preparation method of 3-hydroxy-3-(4-hydroxy-2-oxo-2-hydrogen-chromene-3-yl)indolin-2-one (I). An isatin derivative and a 4-hydroxycoumarin derivative as raw materials undergo a reaction under co-catalysis of a phase transfer catalyst and microwave to produce a compound I. The preparation method has the advantages of mild conditions, simple operation and high yield.

The invention provides a fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2, and the fluorescent probe is called Co-SO2 for short. The fluorescent probe has a structure asshown in a formula (I) which is shown in the description. A synthesis method of the fluorescent probe comprises the following steps: (1) heating 7-diethylamino-4-hydroxycoumarin and POCl3 in DMF (Dimethyl Formamide) for reacting, and separating and purifying, thus obtaining the fluorescent probe. The Co-SO2 fluorescent probe provided by the invention is a simple, fast and sensitive GSH, SO2 and Cys distinguishing reagent; the fluorescent probe can specifically react with GSH, SO2 and Cys under low concentration, and is capable of resisting interference of various active oxygen, amino acid andsulfydryl-containing compounds.

The invention relates to a preparation method of chiral warfarin and chiral warfarin derivatives. The invention aims to provide a preparation method which is simple to operate, has low cost and is is suitable for industrial production. The preparation method comprises the following steps: 1) performing alcohol-aldehyde reaction in a mixed solvent of ethanol and water, wherein the volume ration ofethanol to water in the mixed solvent is 5:2-3 and the dosing molar ratio of substituted benzaldehyde to acetone is 1:2; the aqueous solution is maintained to be alkaline in the reaction process; after the reaction, the product is separated and purified to obtain light yellow solid which is the intermediate product substituted benzalacetone; and 2) in the reaction solvent, performing 1,4-additionreaction between the substituted benzalacetone and 4-hydroxycoumarin under the joint action of chiral catalyst, acetic acid and auxiliary catalyst, wherein the dosing molar ratio of substituted substituted benzalacetone to 4-hydroxycoumarin is 1:1.5-1.6, and the acetic acid is 1-10 times as much as 4-hydroxycoumarin; adjusting the pH value to 7 after the reaction to obtain the chiral warfarin andderivative products of the chiral warfarin.

The invention relates to a method for rapidly detecting a residual quantity of a 4-hydroxycoumarin rodenticide by using a distributed solid phase extraction. The method comprises pre-treating the detected samples by using the distributed solid phase extraction method, and detecting by using an ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS / MS), wherein the sample pre-treatment comprises fully dispersing samples with chloralkane, alcohol and ester solvents, adding proper fillers such as anhydrous sodium acetate, anhydrous magnesium sulfate, etc., performing vortex ultrasonic, centrifuging, taking a supernatant, adding a purifying agent for complete purification, and detecting the centrifuged and purified liquid with UPLC-MS / MS; separating conditions of the UPLC-MS / MS comprises using a C18 reversed phase chromatography, and having a column temperature being 30-60 DEG C, an injection volume being 2-10 [mu]l, and a flow velocity of a mobile phase being 0.15-0.60 ml / min; and detection conditions of the tandem mass spectrometry MS / MS comprises using an electrospray ion source, a negative ionization mode to ionize and a multiple reaction monitoring mode. The method provided by the invention has characteristics of quick extraction and purification, high method selectivity, strong chromatogram specificity and little interference.

The invention discloses a 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and a synthetic method thereof. The synthetic method utilizes multiple components for reaction, and takes 4-hydroxycoumarin, substituted phenylglyoxal and substituted aniline as raw materials, and through reaction of the three components under the action of a catalyst and microwave radiation, the 3-indolyl substituted 4-hydroxycoumarin derivative is obtained through one-step synthesis. The 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative is a brand-new compound of which the molecules contain benzazole and coumarin skeleton and has good bioactivity and a potential application value. Compared with the prior art, the synthetic method has the advantages of short reaction time, simple condition, high yield, high atom economy, convergence, easiness in operation and the like.