27 results about "Aminocoumarins" patented technology

The application belongs to the technical field of medicine, and relates to 3-benzylamino coumarin compounds and application thereof. Experimental results show that the compounds can significantly increase the survival rate of HUVEC cells in a high-sugar environment, and resist blood vessel injury caused by high sugar. The compounds can increase the release amount of NO in HUVEC cells damaged by high sugar, reduce the generation of malondialdehyde, and reduce the generation of tumor necrosis factor alpha.

The invention discloses a preparation method and application of an MOFs (Metal-Organic Frameworks) fluorescent probe for detecting HSO4 <->, relates to preparation and application of a coumarin functionalized MOFs fluorescent probe, and aims to solve the technical problem that the existing fluorescent probe for detecting HSO4 <-> is poor in specificity. The preparation method of the fluorescent probe comprises the following steps: adding ZIF-90 into a methanol solution containing 7-N, N '-diethylaminocoumarin-3-thiosemicarbazide imine, uniformly mixing, heating and refluxing under a stirring condition, and centrifuging, washing and drying the obtained product to obtain the 7-N, N'-diethylaminocoumarin-3-thiosemicarbazide fluorescent probe. A to-be-detected solution is added into a fluorescent probe solution, the concentration of HSO4 <-> is detected by changing fluorescence intensity before and after the to-be-detected solution is added, the linear range is 100-700 mu M, the detection limit is 0.51 mu M, and the response time is 360 s. The fluorescent test paper can also be prepared into portable fluorescent test paper, and HSO4 <-> can be detected according to color change under sunlight or an ultraviolet lamp after the fluorescent test paper is dripped into a solution to be detected. The method can be used in the field of HSO4-detection.

The invention provides an organic light-emitting material, the molecular structural formula is # imgabs0, the organic light-emitting material has the fluorescent property of coumarin, and the pi conjugated system of salicylaldehyde Schiff base is further increased, so that the organic light-emitting material has higher light-emitting efficiency. Trifluoromethyl is introduced to salicylaldehyde and aminocoumarin structures, so that the stability of the material is improved, and the material is more suitable for being used as a core material of an organic light-emitting device. The organic light-emitting material has great potential when applied to the field of organic light-emitting devices. The invention also provides a preparation method of the organic light-emitting material and an organic light-emitting device containing the organic light-emitting material.

The invention discloses an amino coumarin fluorescent whitening agent, the molecular structural formula of which is shown in the specification, n is a positive integer not more than 10, and m is a positive integer not more than 20. The amino coumarin type fluorescent whitening agent prepared by the method has the advantages of cheap raw materials, simple synthesis operation, mild reaction conditions, no need of harsh conditions such as water-free and oxygen-free conditions, and high total yield. The synthesized amino coumarin derivative has proper fluorescence characteristics, can be used as a fluorescent whitening agent for treating polyethylene plastics, and can achieve a whitening effect. When the amino coumarin derivative is applied to whitening, the special effect is that the derivative has good compatibility with polyethylene, and can chemically react with polyethylene, so that the derivative is combined with polyethylene in a firm covalent bond form, and migration of a fluorescent whitening agent is difficult to occur.

The invention discloses a benzo alpha-pyrone imine derivative, a preparation method thereof and application of the benzo alpha-pyrone imine derivative as an antifungal agent. Amino coumarin is used as a basic raw material, and under the action of a catalyst, various benzo alpha-pyrone imine derivatives are synthesized in one step through an aldehyde amine condensation reaction. Tests show that the benzo alpha-pyrone imine derivative disclosed by the invention has antibacterial activity, and particularly, part of compounds have excellent antifungal activity. Therefore, the compound has the potential of serving as a novel plant source pesticide antifungal agent, and lays a foundation for developing novel plant source pesticides.

The present invention relates to the technical field of fluorescent probes, and in particular to a fluorescent probe for rapid detection of nitroreductase, a preparation method thereof, and an application thereof. The present invention provides a fluorescent probe for rapid detection of nitroreductase, a preparation method thereof, and an application thereof. The fluorescent probe is named DM-CN. Due to the quenching effect of the nitro group, DM-CN is almost non-fluorescent. However, when DM-CN reacts with NTR in the presence of NADH, the 4-nitrobenzene substrate is reduced to the corresponding amine by NTR, the ether bond is broken, and then the phenol oxygen undergoes an intramolecular nucleophilic attack on the nitrile group to form iminocoumarin, and then the fluorescence emission is significantly enhanced, thereby achieving specific recognition of nitroreductase. The fluorescent probe DM-CN has the characteristics of high specificity, high sensitivity, high fluorescence intensity response, short response time, and little damage to organisms, and can be used for the detection of nitroreductase in A549 cells and zebrafish.

This invention discloses a water-soluble near-infrared aggregation-induced fluorescence coumarin-quinoline-based viscosity fluorescent probe and its applications. It is synthesized via a Knoevenagel condensation reaction using 7-(N,N′-diphenylamino)-coumarin-3-carboxaldehyde and 1,2-dimethylquinoline iodide as raw materials, catalyzed by p-toluenesulfonic acid and piperidine. Its chemical structure is shown in formula (III). This preparation method features simple reaction steps, mild reaction conditions, and high yield. The fluorescent probe emits fluorescence in the near-infrared region, exhibiting advantages such as a large Stokes shift, low background interference, and minimal photodamage to biological samples. It possesses aggregation / viscosity-induced fluorescence enhancement capabilities and can be used to detect viscosity changes in solutions and cells. This provides an effective research tool for studying physiological activities in cells at different viscosities.

The invention discloses a preparation method and application of a pyrene fluorescent probe for tandem detection of copper ions and picric acid, and relates to the field of detection of copper ions and picric acid, in particular to a preparation method of a pyrene fluorescent probe and application of the pyrene fluorescent probe in tandem detection of copper ions and picric acid. The method solves the problem that the existing fluorescent probe detection method does not realize serial identification of two substances, namely copper ions and picric acid under the same test condition. The preparation method of the fluorescent probe provided by the invention comprises the following step: carrying out condensation reaction on 1-pyrene aldehyde and 1, 3-benzothiazole-2-formyl hydrazine, 6-amino-m-cresol and 7-(diethylamino) coumarin-3-formyl hydrazine respectively to prepare the fluorescent probe. The preparation method is safe and simple, the product yield is high, the purity is good, probe molecules can respond and recognize the copper ions in a high-selectivity mode, meanwhile, a complex of the probe and the copper ions has good recognition selectivity on picric acid, interference of other nitro-aromatic hydrocarbons is avoided, the detection limit is low, and trace detection of the picric acid can be achieved. The method is applied to the field of detection of copper ions and picric acid, the detection process is easy to operate, sensitive, efficient and visual, and the method has wide application prospects in the fields of food, environment and the like.

The invention relates to a hypochlorous acid / viscosity dual-response ratio-type fluorescent probe and a preparation method and application thereof.The hypochlorous acid / viscosity dual-response ratio-type fluorescent probe takes diethylaminocoumarin as an energy donor, (E)-4-(2-(5-(dimethylamino) thiophene-2-yl) vinyl)-1-methylpyridine-1-alato as an energy receptor and piperidine as a linker, and the chemical structure of the fluorescent probe is shown in the formula I. The invention further discloses a preparation method of the hypochlorous acid / viscosity dual-response ratio-type fluorescent probe. The probe can selectively respond to changes of hypochlorous acid and viscosity, along with increase of the concentration of hypochlorous acid in a detection system, the fluorescence emission intensity of the probe at 470 nm is gradually enhanced, the fluorescence intensity of the probe at 594 nm is gradually weakened, and the fluorescence intensity ratio I470 / I594 and the concentration of hypochlorous acid are in a linear relation within a certain range. The probe provided by the invention can realize the change of hypochlorous acid and viscosity in mitochondria in living cells and in a living body, is expected to play a role in industrial production and clinical medicine detection, and has a wide application prospect. # imgabs0 #

The invention discloses a water-soluble near-infrared aggregation-induced emission coumarin-quinolyl viscosity fluorescent probe and application thereof, and the water-soluble near-infrared aggregation-induced emission coumarin-quinolyl viscosity fluorescent probe is realized by the following method: carrying out Knoevenagel condensation reaction on a 7-(N, N '-diphenylamino)-coumarin-3-formaldehyde compound and 1, 2-dimethyl quinoline iodized salt as raw materials under the catalytic action of p-toluenesulfonic acid and piperidine to synthesize the water-soluble near-infrared aggregation-induced emission coumarin-quinolyl viscosity fluorescent probe. The chemical structural formula is shown as a formula (III). The preparation method has the advantages of simple reaction steps, mild reaction conditions and high yield. The fluorescent probe emits fluorescence in a near-infrared region, has the advantages of large Stokes shift, low background interference, small light damage to biological samples and the like, has aggregation / viscosity-induced fluorescence enhancement capability, and can be used for detecting viscosity changes in solutions and cells. And an effective research tool is provided for researching physiological activities under different viscosities in cells.

The invention belongs to the technical field of medicines, and relates to a 3-benzylamino coumarin compound and application thereof. Experimental results show that the compound provided by the invention can significantly increase the survival rate of HUVEC cells in a high glucose environment and resist vascular injury caused by high glucose. The compound provided by the invention can increase the release amount of NO in HUVEC cells damaged by high glucose, reduce the generation of malondialdehyde, and reduce the generation of tumor necrosis factors alpha.

The present invention relates to a method for detecting Cu in aqueous solution. 2+ The fluorescent probe and its preparation method and application are as follows, using methyl hydrazinecarboxylate and 7-diethylaminocoumarin-3-formaldehyde as raw materials, and the primary amine on methyl hydrazinecarboxylate and the aldehyde group on 7-diethylaminocoumarin-3-formaldehyde undergo nucleophilic addition reaction to generate a C=N double bond, and then 1 H NMR, 13 C NMR and ESI-MS were used to characterize its structure. The probe showed bright green fluorescence in aqueous solution, and the fluorescence was quenched after adding copper ions. After mixing the copper ion solution with a concentration gradient change with the probe SJL solution, the fluorescence intensity was measured, and then a graph was drawn with the copper ion concentration as the abscissa and the fluorescence intensity of the mixed system as the ordinate to establish a standard line for the relationship between the concentration gradient change of the copper ion solution and the fluorescence intensity change of the fluorescent probe solution. This compound can be used as a highly sensitive and selective method for detecting trace Cu in aqueous solution. 2+ The complex constant of the fluorescent probe is 1.98×10 5 M ‑1 , with a detection limit as low as 0.6 μM.

The invention discloses a method for preparing a beta-trifluoromethyl substituted enamine compound from trifluoromethyl thianthrene salt, which comprises the following steps: by taking the trifluoromethyl thianthrene salt as a trifluoromethyl source, synthesizing enamine ester or 4-amino coumarin from a first component amine and an electron-deficient terminal alkyne compound; and synthesizing the beta-trifluoromethyl substituted enamine compound from the first component and a second component trifluoromethyl thianthrene salt in two steps. According to the method for preparing the beta-trifluoromethyl substituted enamine compound through two steps, the synthesis method is mild in reaction condition, free of inert gas protection, capable of being carried out at the room temperature in the air atmosphere, good in functional group tolerance and wide in substrate universality, the separation and purification process is easy to operate, and the method is suitable for industrial production. And a target product with high site selectivity can be generated at a good to excellent yield. According to the synthesis strategy, the reaction steps are effectively shortened, the atom economy is greatly improved, meanwhile, the cost required by the preparation process is remarkably reduced, and large-scale industrial production can be achieved.

The application discloses a method for packaging fluorophores based on tris-dolene nanofilm. First, a nanofilm with tris-dolene as a core segment is prepared through gas-liquid interface assembly and condensation reaction, and is carried on a quartz glass. In a wet state, the pore structure of the nanofilm can be maintained without collapsing through freeze-drying treatment. Then, a fluorophore solution is added dropwise on the nanofilm. After the solvent is naturally evaporated, the fluorophore is uniformly dispersed in the nanofilm, spatial and electronic isolation of the fluorophore is realized, and a flexible and uniform fluorescent nanofilm is obtained. The fluorophore packaged by the method includes coumarin (such as 7-(diethylamino) coumarin-3-carbonitrile and coumarin 6), acridine (such as acridine orange), xanthene (such as rhodamine 6G and rhodamine B) and quinonimine (such as Nile red), etc. In addition, the optical properties and sensing behavior of the obtained fluorescent nanofilm are consistent with the optical properties and sensing behavior of the fluorophore in a solution state. Therefore, the application has universality and fidelity.

The present invention provides a complex detection method, which relates to the technical field of boron trifluoride detection, comprising the following steps: measuring I 1 / I 01 ……I n / I 0n ; With the concentration of A1…An as the horizontal axis, I 1 / I 01 ……I n / I 0n Draw a standard curve as the ordinate; take the dilution of the boron trifluoride-ether complex to be tested, Ax; take Bx, measure the fluorescence intensity of Bx, record it as I 0x , mix Ax and Bx to get Cx, measure I x ; Calculation I x / I 0x The value M is taken, and M is brought into the standard curve to determine the concentration value X; the concentration of boron trifluoride in the boron trifluoride-ether complex to be tested is kX. The present invention realizes the concentration detection of BF3 by different enhancement capabilities of different concentrations of BF3 on the fluorescence intensity of 7-diethylaminocoumarin derivatives, and the detection accuracy is high, the sensitivity is high, and the detection limit of BF3 is low.

The invention provides an acrolein fluorescent probe based on a coumarin derivative, a preparation method of the acrolein fluorescent probe and application of the acrolein fluorescent probe in biological detection, and belongs to the field of small organic molecule fluorescent probes. The preparation method of the acrolein fluorescent probe based on the coumarin derivative comprises the following steps: in a solvent environment, carrying out contact reaction on 7-diethylamino coumarin and N-bromosuccinimide to obtain a compound 3; and contacting the compound 3 with 4-aminophenylboronic acid, carrying out a heating reaction, and purifying to prepare the acrolein fluorescent probe based on the coumarin derivative. The acrolein fluorescent probe based on the coumarin derivative is easy and convenient to operate, good in acrolein recognition selectivity, high in response speed, high in sensitivity, good in fluorescence stability and anti-interference performance and capable of rapidly and accurately detecting acrolein in the real-time acrolein detection process; meanwhile, the preparation process of the fluorescent probe is simple, the preparation efficiency is high, and the preparation cost is low.

The invention discloses a piperlongumine derivative shown in a structural general formula (I), a dialkyl amino coumarin fluorescent skeleton is introduced into a piperlongumine pharmacophore, and the piperlongumine derivative which has a lipid droplet targeting fluorescence labeling function and has anti-tumor and anti-aging activity is developed. The piperlongumine derivative disclosed by the invention can be used for lipid droplet imaging in tumor and senescence cells, is used for selectively acting on the tumor cells in vivo, inside and outside, and can selectively remove replicative senescence cells, recover senescence-related markers and gene expression, improve somatic function decline caused by senescence and improve the anti-aging effect of the piperlongumine derivative. And a new way is provided for treatment of clinical related diseases, drug development and preparation of in-vitro preparations or daily necessities.

The application discloses a 7-amino coumarin derivative and a synthesis method and application thereof, and the synthesis method comprises the following steps: placing substituted 3-cyano-4-methyl coumarin and 20% Dabco of the volume of the substituted 3-cyano-4-methyl coumarin in a thick-wall pressure-resistant pipe containing a stirrer, adding tetrahydrofuran solvent, then slowly adding dimethyl butyne diacid in a stoichiometric ratio under stirring, and monitoring the reaction by TLC at normal temperature, removing the solvent under reduced pressure after the reaction is completed, and performing column chromatography separation to obtain the 7-amino coumarin derivative; the application has the advantages of flexible reaction time, cheap and easily-obtained solvent, simple operation, wide application range and the like, and is suitable for industrialized production; the synthesized 7-amino coumarin derivative has certain inhibiting effects on potato dry rot fungus, brassica nigra, tomato botrytis cinerea and apple rot fungus, and can be used as an antibacterial agent.

The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe for rapidly detecting nitroreductase as well as a preparation method and application of the fluorescent probe. The invention provides a fluorescent probe for rapidly detecting nitroreductase as well as a preparation method and application of the fluorescent probe, the fluorescent probe is named as DM-CN, and due to the quenching effect of nitryl, the DM-CN is almost free of fluorescence. However, when the DM-CN reacts with the NTR in the presence of NADH, the 4-nitrobenzene substrate is reduced into corresponding amine by the NTR, an ether bond is broken, then phenol oxygen generates intramolecular nucleophilic attack on a nitrile group to form imino coumarin, and then fluorescence emission is remarkably enhanced, so that specific recognition of nitroreductase is achieved. The fluorescent probe DM-CN has the characteristics of high specificity, high sensitivity, relatively high fluorescence intensity response, short response time, small harm to organisms and the like, and can be used for detecting nitroreductase in A549 cells and zebrafish.

The invention provides a coumarin modified compound of which the structural formula is shown as a formula (I), n is equal to 0 or 1, a novel 3-amino coumarin derivative is successfully synthesized, the structural formula is shown as the formula (I), and the structural formula is shown as the formula (II). The compound provided by the invention shows excellent treatment activity in an acute kidney injury (AKI) model: the compound can be used for remarkably repairing kidney tissue injury in a pathological state and promoting the recovery of the damaged renal tubular epithelial cell form to a normal phenotype; the survival ability of kidney injury cells can be effectively improved, and the cell function is improved; meanwhile, the level of renal function impairment markers such as serum creatinine (Scr) can be remarkably reduced, and it is prompted that the traditional Chinese medicine composition can effectively improve the renal function. The compound provides a new candidate drug for treatment of acute kidney injury, and has important clinical development value and application potential.

The invention discloses a salt-spray-resistant high-strength aluminum alloy and a preparation method thereof, and relates to the technical field of alloy materials. When the salt-spray-resistant high-strength aluminum alloy is prepared, firstly, 5-hydroxymethylfurfural reacts with decamethylene diamine and then reacts with epichlorohydrin to prepare an epoxidized imine monomer; the preparation method comprises the following steps: reacting m-aminophenol with ethyl acetoacetate to prepare an aminocoumarin monomer; the preparation method comprises the following steps: pretreating basalt fibers, activating, and modifying with a coupling agent to obtain modified basalt fibers; the method comprises the following steps: pretreating an aluminum alloy, and carrying out micro-arc oxidation to obtain a micro-arc oxidation aluminum alloy; preparing modified epoxy resin spraying liquid from an epoxidized imine monomer, epoxy resin, an aminocoumarin monomer, polyether amine, the modified basalt fiber and ethyl alcohol, and spraying the surface of the micro-arc oxidation aluminum alloy with the modified epoxy resin spraying liquid to prepare the salt-spray-resistant high-strength aluminum alloy. The prepared salt-fog-resistant high-strength aluminum alloy has the advantages of salt fog resistance, self-repairing, hydrophobicity, high impact strength and good surface bonding strength.

3,3'-carbonyl bis(7-diethylaminocoumarin) compound preparation method, including: (1) in inert gas environment, compound 1 with compound 2 mikhailov acid, compound 3 methanesulfonic anhydride in the first reaction solvent, under the action of metal catalyst, the reaction temperature is 0~150 DEG C, reaction, after reaction is completed, compound 4 is obtained;(2) compound 4 and compound 5 in the second reaction solvent, under the action of catalyst, the reaction temperature is-20~200 DEG C, reaction, after reaction is completed, compound 6 3,3'-carbonyl bis(7-diethylaminocoumarin) is obtained.The key raw material of the application is cheap and easy to obtain;The reaction condition is relatively mild, and the operator is friendly, the reaction yield is high, the product purity is high, the production cost is greatly reduced, and the demand of product ton level production can be fully met.

The invention discloses a trigger type self-degradation polycoumarin monomer molecule and a synthesis method thereof, the monomer molecule comprises a 7-hydroxy coumarin derivative and a 7-amino coumarin derivative, the structures of the 7-hydroxy coumarin derivative and the 7-amino coumarin derivative respectively contain polymerizable hydroxy / amino derivative groups, and the 7-hydroxy coumarin derivative and the 7-amino coumarin derivative are synthesized through multi-step functional group modification. Two types of coumarin derivative monomers are designed and synthesized by combining a classical small-molecular fluorophore with a novel trigger type self-degradable polymer through a high-molecular synthesis means, and a polycarbonate type polycoumarin structure is successfully prepared. The triggering type self-degradation process of polycoumarin macromolecules under the action of an irritant F <-> is explored, the target of a novel triggering type self-degradation polymer structure with classical fluorescent micromolecule coumarin as a main chain skeleton is preliminarily achieved, and the detection sensitivity of a micromolecule fluorescent probe to an analysis object is improved through a chemical method. The construction of a novel molecular amplification analysis method provides guidance and help.

A method for detecting Cu 2+ and CN ‑ Water-soluble polymer coumarin fluorescent probe and its preparation method and application, which involves detecting Cu 2+ and CN ‑ A fluorescent probe, its preparation method, and application. This invention addresses the technical problem that existing fluorescent probes have poor water solubility, leading to difficulty in application in pure water. The structural formula of the fluorescent probe of the present invention is: #imgabs0#, wherein m:n = (22-23):1. Preparation method: COMN is synthesized using 7-diethylaminocoumarin-3-formylhydrazide and diisocyanoethyl methacrylate; using azobisisobutyronitrile as a catalyst, COMN and acrylamide are polymerized to obtain a water-soluble fluorescent probe material, which is used to detect Cu in aqueous solution. 2+ and CN ‑ The minimum detection limits are 7.2nM and 1.27nM respectively, which can be used in the fields of biological imaging and disease detection.

The application discloses a coumarin derivative containing an amide bond and a preparation method and application thereof, and has the characteristics that the specific compound structure of the coumarin derivative is 4-methyl-7-acetylamino coumarin, and the preparation method steps are as follows: 1) 3-hydroxyphenyl ethyl carbamate is prepared by amidation reaction of m-aminophenol and ethyl chloroformate; 2) 4-methyl-7-ethoxycarbonylamino coumarin is prepared by esterification reaction of 3-hydroxyphenyl ethyl carbamate and ethyl acetoacetate; 3) 4-methyl-7-aminocoumarin is prepared by esterolysis reaction of 4-methyl-7-ethoxycarbonylamino coumarin and a mixture of glacial acetic acid and concentrated sulfuric acid; and 4) 4-methyl-7-acetylamino coumarin is prepared by esterification reaction of 4-methyl-7-aminocoumarin, pyridine and acetic anhydride, and the advantages are that the compound has good antiviral and killing effects on white spot syndrome virus, the synthesis method is simple, and the conversion rate is high.

The application discloses a novel fluorescent compound, a preparation method thereof and applications of the fluorescent compound in mitochondrial fluorescence imaging and viscosity detection, wherein the fluorescent compound is combined with quinoline or naphthyridine and malonitrile to form an electron-withdrawing part, and is connected with an electron-donating auxiliary chromophore 3-formyl-7-diethylaminocoumarin through a carbon-carbon double bond to form a neutral molecule with a typical D-pi-A structure. The fluorescent compound prolongs the conjugation degree of quinoline or naphthyridine to reach the red channel, has an aggregation-induced emission phenomenon, has small cytotoxicity, can be used for labeling mitochondria in biological imaging, and has an obvious viscosity response in optical testing, and can be used for mitochondrial viscosity detection. In addition, the preparation method of the fluorescent compound is simple, and raw materials are easy to obtain, so that the fluorescent compound provides a low-cost option for mitochondrial red fluorescence labeling, and has a good application prospect in mitochondrial fluorescence imaging and mitochondrial viscosity detection.

The invention discloses a copper (II) complex with anticancer activity as well as a preparation method and application thereof, and belongs to the technical field of complexes. According to the preparation method, CuCl22H2O, CuBr2 or Cu (NO3) 2.3 H2O is subjected to a reaction with benzoyl hydrazone 3-acetyl-7-N, N-diethylamino coumarin respectively, and the complex is obtained. The obtained complex has certain anti-proliferative activity to four cell lines, namely HeLa, MCF-7, A549 and HepG-2, and the anti-proliferative activity is obviously superior to that of a ligand, particularly, the complex shows relatively excellent anti-proliferative activity to the MCF-7 cell line, and the toxicity to normal HUVEC cells is also obviously lower than that of cis-platinum. The copper (II) complex provided by the invention has good anti-cancer activity, the preparation method is simple, the toxicity is small, and a new thought is provided for the development of anti-cancer drugs.