47 results about "8 aminoquinolines" patented technology

The invention relates to the synthesis of N-acyl-8-aminoquinoline derivatives and application thereof as fluorescent molecular probes. The invention takes 8-aminoquinoline as a matrix, can introduce substitutional groups at position 2, 4 and 5 of the quinoline matrix, and can acylate on an amino group to synthesize a series of novel acylaminoquinoline derivatives. The compounds with relatively simple structures and easy synthesis can be used for fluorescence detection of transition and heavy metal ions in solutions, show high sensitivity and selectivity, and are successfully applied to the fluorescence imaging detection of zinc ions in living cells. The compounds are expected to be widely applied in the fields such as analytical inspection of transition metal and heavy metal ions and the catalysis of metal complexes in biological tissues, cells, environment, medicine, and industrial and agricultural production and so on.

The invention discloses a fluorescent probe based on an 8-aminoquinoline derivative and a synthetic method and application thereof. The structural formula of the fluorescent probe is shown in the specification. The specific preparation method comprises the steps that acetonitrile is used as a solvent, raw materials comprising 2-chlorine-N-(quinoline-8-base) acetamide and 2-propargylamine are fed at the mole ratio being 1:1-1.5:1, a certain amount of KI and N, N-DIPEA are added, backflowing is carried out overnight, pressure is reduced, acetonitrile is obtained in a back-out mode, ethyl acetate is extracted, anhydrous sodium sulfate drying is carried out overnight, filtering is carried out, ethyl acetate is obtained in a back-out mode, the obtained oily matter is purified through silica gel column chromatography, the ethyl acetate and petroleum ether with the ratio being 1:1-1.5(v / v) is used as eluent for separation, and a light yellow solid compound L is obtained. The fluorescent probe based on the 8-aminoquinoline derivative has the advantages of being easy to synthesize, good in water solubility, capable of recognizing Zn<2+> in a water environment system and a biological cell system, capable of monitoring, analyzing and tracking sulfur ions and pyrophosphate ions and good in sensitivity.

The invention relates to a yellow pigment for a color liquid crystal filter, which consists of at least two compounds. The compounds include a compound I and a compound II. A preparation method for the pigment comprises the following procedures of: A, synthesizing a yellow pigment crude product of which the structural formula is the compound I by 2-methyl-8-aminoquinoline and tetrachlorophthalic anhydride serving as basic raw materials; and B, performing pigment processing on the yellow pigment crude product. The pigment processing procedure comprises the following steps of: 1, pre-grinding the yellow pigment crude product; and 2, performing pigment postprocessing on the pre-ground yellow pigment crude product. The yellow pigment prepared by the method has high transparency, brightness and contrast, and has good fluidity in a liquid dispersoid for coloring the color filter.

The invention discloses a rhodamine B derivative containing an 8-aminoquinoline group, a preparation method, an application and a method for carrying out fluorescence analysis on Cr<3+> and Cu<2+>. The rhodamine B derivative containing the 8-aminoquinoline group is capable of selectively and quantitatively detecting chromium ions (Cr<3+>) in acetonitrile, and is capable of selectively and quantitatively detecting copper ions (Cu<2+>) in ethanol and generating an obvious fluorescence increment effect. The rhodamine B derivative containing the 8-aminoquinoline group is simple in synthesis method, and is capable of quantitatively detecting different heavy metal ions Cr<3+> and Cu<2+> in different solvents at high selectivity and high sensitivity, is a dual-functional fluorescence probe, and has a good application prospect in the fields of environment analysis and detection.

The invention relates to a preparation method of N-phenyl-8-aminoquinoline and belongs to the technical field of organic chemical synthesis. The preparation method of the N-phenyl-8-aminoquinoline is characterized by comprising the following steps: reacting 8-aminoquinoline with acyl chloride to obtain acyl 8-aminoquinoline, and performing arylation reaction on the acyl 8-aminoquinoline and hypervalent iodonium salt on an amino group under the catalysis of copper salt to obtain an N-phenyl-N-acyl-8-aminoquinoline derivative; performing deacylation reaction on the N-phenyl-N-acyl-8-aminoquinoline to obtain the N-phenyl-8-aminoquinoline. The preparation method of the N-phenyl-8-aminoquinoline has the beneficial effects that the operating steps are simple, the reaction condition is mild, and the N-phenyl-8-aminoquinoline can serve as an excellent chelating agent and can be applied to detection of metal ion content.

The invention belongs to the field of chemical analysis and testing and particularly relates to a preparation method and an application of a 1,3-position symmetric squarylium cyanine probe based on carboxamidoquinoline. Firstly, a mixture of 8-aminoquinoline and 2-chloroacetyl chloride is subjected to ice-bath stirring in a dichloromethane solvent, a product and p-phenylenediamine are subjected to reflux in a methanol solvent, then 3,4-diethoxy-3-cyclobutene-1,2-dione and a product are subjected to reflux reaction in toluene and n-butyl alcohol, and a final product is obtained through separation and purification. The obtained squarylium cyanine compound has excellent ionic selectivity and facilitates silver ion detection.

The invention discloses core-shell-structured nano-particles modified with 8-aminoquinoline derivative, and a preparation method and an application thereof. According to the invention, the core-shell-structured nano-particles with iron oxide as cores and silica as shells are modified with the 8-aminoquinoline derivative. The method comprises the steps that: ferric chloride hexahydrate and sodium acetate dissolved in ethylene glycol are placed under a sealed state, and are subjected to a reaction under the temperature of 200-210 DED C, such that a precipitate iron oxide nano-particles are obtained; the nano-particles are dispersed in ethanol; ammonia water, deionized water, ethanol and a tetraethyl orthosilicate ethanol solution are sequentially dropped into the solution; ultrasonic reaction is carried out, and nano-particles are obtained; the nano-particles are sequentially added into toluene, such that a suspension liquid is obtained; N-(quinolin-8-)-2-(3-triethoxysilyl-propylamino)-acetamide is dissolved in toluene, such that a QIOEt toluene solution is obtained; the two are mixed and are subjected to an ultrasonic process; and a reflux reaction is carried out under the temperature of 130-150DEG C, such that a target product is prepared. The product can be widely used for rapidly detecting trace amounts of divalent zinc ions in a solution.

The invention discloses a preparation method of 2-methyl-8-aminoquinoline. The preparation method is characterized in that the 2-methyl-8-aminoquinoline is prepared from o-nitrophenol through a process line of reduction, cyclization and amino substitution. An oxidant is selected from one or more of the o-nitrophenol, ammonium ceric nitrate, vanadic acid and iron oxide, and a catalyst is selected from ammonium chloride-cobalt chloride, palladium-aluminum trioxide or aluminum trioxide-silicon dioxide.

The invention discloses an 8-aminoquinoline derivative, preparation thereof and application thereof to preparation of anti-malaria and anti-tumor drugs. In formula (I), R1 refers to phenyl, substituted phenyl, C5-C6 aromatic ring, C1-C10 alkyl, C1-C10 alkoxy or C1-C10 substituted alkyl, a substituting group of the substituted phenyl refers to methyl, chlorine, nitryl, fluorine or methoxyl, the substituted alkyl refers to leucine-5-azide quinoline, R2 refers to H or methyl, R3 refers to -N3, -NH2 or (formula), and R4 refers to phenyl, C5-C6 aromatic ring or C1-C10 alkyl. The 8-aminoquinoline derivative and preparation and application thereof have the advantages that simplicity, high efficiency and rapidity in operation process are achieved, raw materials are easily available, the anti-malaria activity (IC50<0.1 micrometer) of the 8-aminoquinoline derivative is improved by more than 6 times than that (IC50=0.64 micrometer) of 8-aminoquinoline, and the anti-tumor activity thereof is improved by more than 10 times than that of 8-aminoquinoline.

The invention discloses an alpha-benzyl-modified diaryl phosphonic compound and a preparation method thereof. The method is a novel method for preparing a mono-substituted benzyl phosphamide compound from a copper salt as a catalyst, P,P-diaryl-N-(8-aminoquinoline) phosphamide as a raw material, methylbenzene and a derivative thereof as a solvent and a benzyl source and peroxide as an oxidizing agent under a nitrogen condition at high yield and high selectivity. Corresponding alpha-benzylated arylphosphonic acid and alpha-benzylated aryl hydrogen phosphonate can be prepared from alpha-benzylated aryl phsophonamidate through adding alkali and a reducing agent. The method is simple in reaction condition, easy to operate, low in cost, green and environmentally friendly in preparation process, high in conversion rate and yield of a target product; the target product can be prepared at high yield after the reaction scale is amplified by 50 times; and the alpha-benzyl-modified diaryl phosphonic compound has a good industrial application prospect.

The invention discloses a novel process for producing pigment yellow PY138. The novel process comprises two steps, i.e. a condensation reaction step and a refining reflux step, wherein firstly tetrachlorophthalic anhydride and 2-methyl-8-aminoquinoline is added into a solvent to be heated to react, then after the decompression and distillation, the distilled gas is introduced into 98 percent sulfuric acid to be acid cooked, the acid cooked solution is hydrolyzed and filtered, then the filtrate is heated and press filtered in an alcohol solvent, the press filtered filter cake is dissolved, heated, stirred and thermally insulated in a reflux solvent, finally the solution is evaporated and refluxed, cooled, press filtered and dried to obtain the pigment yellow 138. In the process for preparing the pigment yellow 138, the raw material utilization rate is high, the production cost is lower than that of the prior art, the prepared pigment yellow 138 is high in purity, the color is bright, the coloring capability is high, the heat resistance, acid resistance and alkali resistance are more excellent compared with that available on the market, the environmental pollution is small, the production efficiency is high, and the novel process is suitable for the mass production.

The invention relates to a biological fluorescent molecular probe and its synthetic method and application, in particular to an oxalyl aminoquinoline derivative fluorescent molecular probe and a preparation method and application thereof and aims to solve the technical problem that an existing molecular probe is made from various synthetic materials under harsh synthetic conditions. A structural general formula of the oxalyl aminoquinoline derivative fluorescent molecular probe is shown as follows; wherein R is an alkoxy group, an amino group, an alkyl amino group, an aromatic amino group or a hydroxyl alkyl group. A first preparation method comprises: reacting 8-aminoquinoline with diethyl oxalate to prepare an intermediate, and reacting the intermediate with amine to obtain a mono-substituted oxalyl aminoquinoline derivative fluorescent molecular probe; a second preparation method comprises: adding 8-aminoquinoline and diethyl oxalate into diethyl oxalate for reacting, and purifying to obtain a bis-substituted oxalyl aminoquinoline derivative fluorescent molecular probe. The molecular probe is useful in detecting zinc ions that are zinc ions in a solution or zinc ions in an organism.

The invention discloses an aromatic planar Schiff-base copper complex. The chemical formula of the aromatic planar Schiff-base copper complex is [CuL(H2O)](ClO4)-H2O, wherein L is 8-aminoquinoline salicylidene Schiff-base, and ClO4 is perchlorate. The preparation method of the aromatic planar Schiff-base copper complex comprises synthesis of a ligand L and synthesis of an aromatic planar Schiff-base copper complex. The synthetic process is simple and has good selectivity and stability. There is intercalation of intermediate bonding between the aromatic planar Schiff-base copper complex and CT-DNA. Under the close physiological condition of existence of a redox inducer, it shows an obvious cutting effect on Pbr322 DNA; and ultraviolet light has a certain promotion effect on the cutting effect. The Pbr322 DNA can be fractured through an auto-oxidation approach, and a hydroxyl radical active matter is generated in the cutting process.

The invention discloses a synthesis method of a Beta-silicon group-substituted amino acid derivative. The synthesis method comprises the following steps: using amino acid of N-terminus amino group-protected and carboxy-terminus-introduced 8-aminoquinoline and hexamethyl disilane as raw materials; using hexamethyl disilane as a silicon group forming agent; using palladium acetate as a catalyst; using substituted quinone as an oxidant; using silver salt and acetate as additives; performing silicon group reaction in an organic solvent; performing column chromatography separation and purification to obtain the Beta-silicon group-substituted amino acid derivative. The synthesis method provided by the invention is mild in reaction condition, simple in process, convenient to operate and high in stereoselectivity.

The invention discloses 8-aminoquinoline Schiff base and zinc rhodanate metal complex and a preparation method thereof. The preparation method comprises the steps of dissolving 8-aminoquinoline, salicylic aldehyde and triethylamine into an organic solvent, and performing backflow and cooling while stirring; adding an organic solution in which zinc perchlorate hexahydrate and potassium thiocyanate are dissolved, stirring for 7 days at normal temperature, filtering, enabling filter liquor to naturally volatilize, and obtaining yellow tabular crystals after 35 days; filtering, and washing filter cakes with diethyl ether, so as to obtain a complex single crystal with a molecular formula of C18H15N3O2SZn. The complex forms a 3d supramolecular structure through hydrogen bonds and Pi. . . Pi aromatic nucleus accumulation.

The invention relates to a preparation method of N-phenyl-N-[8]quinolyl-4-fluoro-benzamide. The preparation method comprises the following steps: adding 4-fluoro-benzoyl 8-aminoquinoline, anhydrous copper acetate, triphenyl bismuth, sodium bicarbonate, a 1,4-dioxane solvent and one No.5 magneton into a reactor in sequence; after introducing condensed water into a condensing tube from bottom to top, putting the reactor into an oil-bath pot and carrying out heating reaction; after finishing the reaction, pouring a reaction solution into a separating funnel; adding distilled water and extracting with ethyl acetate for 3 times; combining obtained organic phases and carrying out spin-drying through a rotary evaporator; separating and purifying a crude product through a column chromatography to obtain the N-phenyl-N-[8]quinolyl-4-fluoro-benzamide, wherein the yield is 93 percent. The preparation method provided by the invention has moderate conditions; a cheap metal copper catalyst is adopted, nitrogen gas protection is not adopted, and an oxidant is not needed, so that the preparation method has relatively good economic efficiency and is environmentally friendly; the product can be applied to various fields including drug synthesis, pesticide synthesis, synthesis of corrosion inhibitors of buildings and the like.

The present invention relates to a heterocyclic di-triazene compound, di-(8-quinoline diazoaminoazobenzene)-biphenyl (BQDADB). 8-aminoquinoline is treated through diazotization by sodium nitrite under the acidic conditions and then reacts with benzidine in the alcohol solution; thus the compound can be prepared. The compound can not only be used as an excellent chromogenic agent, but also can be used as a fluorescent reagent with high sensitivity and high selectivity. And the compound can be used for testing the fluorescence of metal ions, in particular testing the Cu(II) in the alkaline medium.

The invention discloses an efficient synthesis method of substituted aspartic acid.The efficient synthesis method includes: using amino acid of nitrogen terminal all-protected and carboxyl terminal introduced 8-aminoquinoline as a raw material; adopting chloroformate as an ester group source, palladium acetate as a catalyst and silver salt and iodine element as additives; in an organic solvent, reacting for 16 h at 120 DEG C or 140 DEG C, and obtaining a substituted aspartic acid derivative through column chromatography purifying separation.The synthesis method is mild in reaction condition, simple in process and convenient and quick to operate, and ester groups can be well introduced into an amino acid substrate directly to obtain the aspartic acid derivative high in stereoselectivity.

The invention discloses a fluorescent dye with a fluorescence opening property and a preparation method and application thereof. The fluorescent dye is a 5-azido-8-aminoquinoline fluorescent dye, andadopts a structural formula shown as a formula (I), wherein in the formula (I), R1 is H, styrene, buty-1, 3-dien-1-ylbenzene or 4-vinyl phenol, R2 is H or styrene and R3 is H or styrene. The fluorescent dye has the fluorescence opening property, and after 1, 3-dipolar cycloaddition with alkyne, a fluorophore with the high quantum yield is provided for formation of triazole. The fluorescent dye hashigh click-through rate and excellent light stability as a fluorescent probe, and provides a powerful tool for living cell biological imaging.

The invention discloses a dendritic 1, 4-diene amide derivative shown as formula (1) and a synthesis method thereof. The specific synthesis method includes: placing an alkenyl quinoline amide compound, an allyl methyl carbonate derivative, a transition metal salt catalyst and an additive in an organic solvent, carrying out heating reaction in an argon atmosphere, and carrying out aftertreatment onthe reaction liquid at the end of the reaction to obtain the dendritic 1, 4-diene amide derivative. Under mild conditions, the method provided by the invention utilizes 8-aminoquinoline amide as N, N-double coordinated guide group, takes allyl methyl carbonate as the alkenylation reagent, and efficiently realizes hydrocarbon alkenylation reaction of alkenyl and carbon site, the obtained productsare all brand new compounds, the reaction substrate has wide application range, the raw materials are economical and easily available, no exogenous oxidant is needed, the operation is simple, and thehighest yield can reach 93%, therefore the method has wide application prospect and economic value.

The invention discloses a preparation method for an aromatic phosphine compound. The method is a new method for realizing arylation of ortho-position C-H bond of the aromatic phosphine compound in high yield and selectivity. In the oxygen atmosphere, copper is used as a catalyst, P,P-diaryl-N-(8-aminoquinoline)-phosphamide is used as a raw material, and an aryl boronic acid is used as an aryl source. The method is capable of realizing the arylation of the ortho-position C-H bond of the aromatic phosphine compound catalyzed by cheap metal. The reaction condition is moderate, the operation is easy, the preparation process is green and environmental, and the conversion rate and productive rate of a target product are high. The problems in other synthetic methods that the reaction temperature is higher, the precious metal catalyst is used necessarily, more wastes are produced and the environment pollution is easily caused and so on can be solved, and the method has good industrial application prospect.

The present invention is concerned with the development of novel 8-aminoquinoline analogs in the treatment and prevention of malaria and the said compound has broad spectrum of activity against the blood as well as tissue stages of the human malaria parasites makes these compounds very attractive in the cure and prevention of malaria caused by drug-sensitive and multidrug resistant strains and also it is expected that development of these compounds as ideal antimalarial agents may lead to suppression as well as radical cure of the malaria infection with single drug therapy.

The invention discloses a synthetic method of an aryl sulfone compound containing a C (sp2)-S bond. The synthetic method comprises the following steps: 1, a 5-chloro-8 aminoquinoline part as shown ina formula (I) is used as a guide group and is prepared from 5-chloro-8 aminoquinoline aromatic amide and aryl sulfinate (II) under the action of a transition metal system. The sulfonylation reaction of the C (sp2)-H bond is achieved through air oxidation, and the compound containing the C (sp2)-S bond shown in the formula (III) is obtained. According to the method, the raw materials are simple andeasy to obtain, operation is easy and convenient, and a concise and efficient synthetic method method is provided for synthesizing aryl sulfonyl compounds.

The invention relates to a preparation method of N-phenyl-N-[8]quinolyl-benzamide, comprising: adding benzoyl-8-aminoquinoline, anhydrous copper acetate, triphenyl bismuth, sodium bicarbonate, 1,4-dioxane solvent and a No. 5 magneton successively into a reactor; introducing condensate into a condensing pipe from bottom to top, placing the reactor in an oil bath, and heating for reacting; after reacting, pouring reacted liquid into a liquid-diversion funnel, adding distilled water, and extracting with ethyl acetate three times; combining the obtained organic phases, rotationally drying by a rotary evaporator, and subjecting the crude product to column chromatographic separation and purification to obtain the N-phenyl-N-[8]quinolyl-benzamide; the yield is 99%. The preparation method has mild reaction conditions, the cheap metallic coper catalyst is used, no nitrogen protection is provided, oxidants for use are not required, the economy is high, and the environmental friendliness is good; the finished product is applicable to the fields of drug synthesis, pesticide synthesis, coating and dye synthesis and the like.

The invention relates to the synthesis of N-acyl-8-aminoquinoline derivatives and application thereof as fluorescent molecular probes. The invention takes 8-aminoquinoline as a matrix, can introduce substitutional groups at position 2, 4 and 5 of the quinoline matrix, and can acylate on an amino group to synthesize a series of novel acylaminoquinoline derivatives. The compounds with relatively simple structures and easy synthesis can be used for fluorescence detection of transition and heavy metal ions in solutions, show high sensitivity and selectivity, and are successfully applied to the fluorescence imaging detection of zinc ions in living cells. The compounds are expected to be widely applied in the fields such as analytical inspection of transition metal and heavy metal ions and the catalysis of metal complexes in biological tissues, cells, environment, medicine, and industrial and agricultural production and so on.

The invention discloses a preparation method of sodium phenylbutyrate. The preparation method comprises the steps that in the inert atmosphere, materials and anhydrous 2,3-butanediol are added into areaction vessel, and mixing is conducted uniformly, wherein the related materials include allyl palladium (II) chloride dimer, 2-(dicyclohexylphosphino)-1-phenyl-1H-pyrrole, N-(8-aminoquinoline)butyl-3-enamide, lithium acetate, bromobenzene, cyanoacetic acid and water; the reaction vessel is placed in an oil bath at 125-135 DEG, a vigorous stirring reaction is conducted for 12 hours, a reaction product is purified through a silica gel column, and a compound with a guiding group is obtained; the compound is added into an ethanol solvent containing sodium hydroxide, the mixture is heated to 130-140 DEG C, a reflux reaction is conducted for 12 hours, the reaction product is subjected to vacuum distillation to remove the solvent, extraction is conducted, a water layer is collected, vacuum distillation is conducted to remove water, and a sodium phenylbutyrate preparation is obtained. The method has the advantages of being high in reaction site selectivity and yield, mild in reaction condition and simple in reaction and aftertreatment purification process.

The invention discloses a beta-deuterated valproic acid preparation method, which sequentially comprises: carrying out an intramolecular valproyl carbon skeleton beta-site directed deuteration reaction on 8-aminoquinoline valpromide in D2O by using palladium acetate as a catalyst to generate deuterated 8-aminoquinoline valpromide, wherein the deuteration reaction is performed in a sealed state; and carrying out a hydrolysis reaction on the deuterated 8-aminoquinoline valpromide in an organic solvent under the action of an alkali under a normal pressure reflux condition, and carrying out acidification treatment to obtain beta-deuterated valproic acid. According to the present invention, the method has advantages of high selectivity, simple reaction post-treatment, easily available raw materials and environmental protection, and provides the efficient and accurate method for the efficient synthesis of beta-deuterated valproic acid.

The invention discloses quinoline triarylamine and a preparation method thereof. A substituted 8-aminoquinoline compound (I) and a carbazole compound (II) are used as substrates, and a nickel catalystwith the mole fraction of 1% to 30% (relative to a primary amine compound I, the same below) and 2-5 molar equivalents of alkali are added, 2 mL of an organic solvent serves as a solvent, and the reaction mixture is stirred for reaction at 25-160 DEG C under a nitrogen atmosphere for 1-48 hours, a saturated ammonium chloride solution is added for quenching after the reaction is complete, extraction is executed with a polar organic solvent, anhydrous sodium sulfate or anhydrous magnesium sulfate is added for drying, and the target product triarylamine compound (III) is obtained through concentration by a rotary evaporator and separation by column chromatography to obtain. The method has the advantages of cheap catalyst, high yield, simple and convenient operation, no generation of harmfulbyproducts and the like, and has certain feasibility for realizing industrial production. The synthesized quinoline triarylamine compound can be converted into various functional molecules through various cascade reactions or cross coupling reactions, and has the potential application value in the fields of biomedicine and materials.

The invention discloses an amide Boc de-protection method. The amide Boc de-protection method includes carrying out reaction on Boc protected amide III and amine IV under the condition of the presenceof palladium catalysts to generate new amide V. 8-aminoquinoline can be used as a guide group to be applied to chemical reaction, a process for synthesizing the new amide by means of de-protection isprovided, protecting groups can be easily removed by means of palladium catalysis, the new amide can be generated, and the reaction is high in efficiency. The amide Boc de-protection method has the advantages of environmental friendliness, recyclability and the like.