22 results about "Bis indole" patented technology

The invention provides application of a bisindole compound XQ-016 in treatment of osteosarcoma, and belongs to the technical field of biological medicines. The bisindole compound XQ-016 can inhibit proliferation, migration and invasion of tumor cells by adjusting an STAT3 / p53 signal channel, inducing G1 phase cell cycle arrest and inhibiting MMP2 / MMP9 expression, shows remarkable anti-tumor activity, is a promising treatment choice in tumor treatment, and can be used as an effective component in anti-tumor drugs.

The invention discloses a preparation method of a 3-substituted-2, 3 '-bisindole compound, and belongs to the field of organic synthesis. According to the method, 3-iodoindole with indole N-H protected by p-toluenesulfonyl and olefin are used as initial raw materials and are stirred to react in an organic solvent at 60-120 DEG C under the action of a palladium catalyst, norbornene, a phosphine ligand, an accelerant and alkali, and the 3-substituted-2, 3 '-bisindole compound can be obtained. The raw materials used in the method are cheap and easy to obtain, the reaction process is mild, the substrate universality is good, and the method has high step economy and practicability.

The invention discloses a bisindole compound as well as a synthesis method and anti-tumor application thereof. The molecular structure of the bisindole compound is shown in the specification. The bisindole compound XQ-010 has the remarkable effects that the bisindole compound XQ-010 can be used as an IL-6 / STAT3 signal channel regulator for tumor treatment, particularly has unique advantages in the aspect of inhibiting tumor growth and metastasis based on the inhibiting effect of the bisindole compound XQ-010 on CD133 + and CD44 + tumor stem cells, and has important clinical application value and development prospect.

The invention discloses an intermediate and a preparation method thereof, and a synthesis method and application of bisindolylbenzene natural products. The intermediate has the following structural formula: R1 and R2 are independently selected from H, hydroxyl, alkyl of C1-6, alkoxy of C1-6, benzyloxy and OTf group. The invention provides an intermediate with a novel structure, and the intermediate can be used for preparing a series of bisindolylbenzene natural products. The reaction is simple; the yield is high.

This invention belongs to the field of organic drug synthesis and discloses a method for synthesizing bisindole cyclic compounds using di-tert-butyldiazide ketone as an amine source. Under the protection of an inert gas, 2-(2-iodophenyl)-indole 1, di-tert-butyldiazide ketone 2, a palladium catalyst, a ligand, and a base are added to an organic solvent in a specific ratio and reacted at a heating temperature. After the reaction, the bisindole cyclic compounds shown are prepared, and the target product is separated after the reaction is complete. This invention uses di-tert-butyldiazide ketone as a nitrogen source. This method has the advantages of being simple and novel, and can synthesize a series of bisindole cyclic compounds and their derivatives with high efficiency.

The present invention relates to the technical field of organic synthesis, and discloses a 2, 3 '-axial bisindole compound preparation method, which comprises: dissolving a 3-indolyl derivative in a solvent, adding a catalyst, and carrying out a stirring reaction at a temperature of 80-120 DEG C to prepare the 2, 3'-axial bisindole compound. According to the invention, a metal-free cyclization strategy is adopted, the dependence on an expensive metal catalyst in a traditional synthesis method is broken through, and the construction of an axial 2, 3 '-bisindole skeleton can be realized without adding any metal catalyst. The breakthrough not only avoids the problems of high cost, tedious subsequent separation and purification and the like caused by a metal catalyst, but also has remarkable step economy and atom economy, greatly simplifies the synthesis process, and realizes innovation of the traditional method from the level of reaction mechanism.

The invention provides a chromone bisindole derivative as well as a preparation method and application thereof. According to the derivative, a chromone ketone ester compound with different substituted benzene rings is used as a raw material, the 3-site of the compound is structurally modified, and the compound and indole are subjected to an addition reaction to successfully synthesize 21 chromone bis-indole derivatives. The derivative contains chromone and indole dominant skeletons, has various biological activities, and especially has an outstanding anti-tumor effect. The method has the advantages of simple operation, short reaction time, high yield, easily available raw materials, good air stability and wide applicability, can provide a compound source for biological activity screening, and has important application value for drug screening and pharmaceutical industry.

A method for synthesizing 6-substituted 5,6-dihydropyridinebisindole compounds includes the following steps: 1) mixing a bisindole derivative with DMF, stirring at a certain temperature to dissolve the bisindole derivative, and then adding an organic amine; 2) dissolving a catalyst CuCl2·2H2O in DMF, adding the CuCl2·2H2O DMF solution to the mixed solution from step 1), and reacting; 3) repeatedly extracting with ethyl acetate and ultrapure water, collecting the organic layer, removing water and ethyl acetate, eluting the collected solution, removing the solvent, and obtaining the product. This method efficiently synthesizes 6-substituted 5,6-dihydropyridinebisindole compounds through a one-step reaction of a bisindole derivative with an organic amine, providing a synthetic basis for the study of the biological functions of these compounds.

The invention provides an asymmetric synthesis method of a chiral bisindole compound, and belongs to the technical field of organic synthesis. According to the present invention, the indole compound and the chiral sulfinyl ketimine compound are adopted as the substrates, and the novel asymmetric Friedel-Crafts reaction is performed under the conditions of bimetallic catalysis and coordination so as to achieve the efficient synthesis of the chiral bis-indole compound; the bimetallic catalytic system has the advantages of mild reaction conditions, excellent stereoselectivity, wide substrate applicability, high economic benefits and the like, provides an efficient synthesis way for synthesis of chiral bisindole compounds, and has a good industrial prospect.

The invention discloses a method for stereoselectively synthesizing chiral bisindole with antitumor biological activity, and relates to the technical field of medicine synthesis. The chiral bisindole derivative provided by the invention has an obvious inhibition effect on the growth of human cervical cancer cells (Hela), pancreatic cancer cells (Panc-1) and human bone marrow neuroblastoma cells (Sy5y), shows good anti-tumor biological activity, and has important positive significance for promoting the research and development of anti-tumor drugs; a carbon-nitrogen bond breaking strategy is creatively adopted, a chiral phosphoric acid catalyst is used for catalysis, a nucleophilic indole C2 site stereoselective reaction is achieved, a high-quality path is provided for chiral bisindole compound synthesis, meanwhile, the method has the advantages that reaction raw materials are easy to obtain, conditions are mild, enantioselectivity, chemical selectivity and regioselectivity are high, and the method is suitable for industrial production. The atom economy is high.

The present application relates to a kind of containing double indole quaternary ammonium salt, preparation method and its application in catalytic preparation of five-membered ring carbonate, the structure of containing double indole quaternary ammonium salt in containing double indole quaternary ammonium salt structure is at the end of containing double indole quaternary ammonium salt, containing alkyl chain hydrocarbon structure is connected on the nitrogen atom of indole ring of containing double indole quaternary ammonium salt;By two end halogen alkyl and indole reaction, the compound with two indole groups in end position is generated in medium chain hydrocarbon, further reaction with halogenated hydrocarbon is generated containing double indole quaternary ammonium salt;Under the condition of containing double indole quaternary ammonium salt as single catalyst, carbon dioxide and epoxy compound are reacted to obtain five-membered ring carbonate.The five-membered ring carbonate is prepared by catalysis using the present application, other cocatalyst is not needed, with the advantages of high efficiency, low cost, easy separation, catalyst raw material is easy to obtain, preparation method is simple, and catalytic efficiency is high.

The application discloses a kind of diindole derivatives and preparation method thereof, it is left-handed or right-handed optical active body or racemate with the following structural formula;Its preparation includes with isoindoline group propargyl alcohol compound and 2-indole methanol compound as raw material, with organic phosphoric acid catalyst as catalyst, reaction is obtained in organic solvent diindole derivative.The application utilizes catalytic tandem reaction method to synthesize diindole derivative, reaction condition is mild, process is simple, operation is convenient, the potential fluorescent property and biological activity of obtained product, this will have important significance to fluorescent material and synthesis drug screening.

This invention discloses an N-N axial chiral phase-transfer catalyst, its synthesis method, and its applications, belonging to the field of asymmetric catalytic synthesis technology. Using chiral 2,4-pentanediol and N-Boc-indolephenol as starting materials, this invention efficiently constructs an N-N axial chiral biscarbazole cyclic ether skeleton through a five-step reaction involving Mitsunobu etherification, deBoc protection, PIDA oxidative cyclization, radical bromoxymethylation, and intramolecular quaternization. This method eliminates the need for complex chiral resolution and noble metal coupling, employs mild reaction conditions, uses readily available and inexpensive starting materials, achieves high overall yield, and yields a product with an axial chirality ee value ≥98%. The resulting catalyst possesses excellent conformational rigidity, chiral induction ability, and phase-transfer performance, exhibiting broad substrate applicability. It also possesses bisindole ring bioactivity, making it widely applicable in asymmetric catalytic synthesis in pharmaceuticals, fine chemicals, and other fields, and providing new directions for the development of antibacterial and antitumor biomaterials.

The application provides a preparation method and application of a dual-indocyanine green diagnosis and treatment integrated compound with a stimulus response, provides a micro-nano structure formed by self-assembly of a compound with a structure shown in formula (I) or an isomer, a pharmaceutically acceptable salt, a hydrate or a solvate thereof in an aqueous solution, and preparation of a pharmaceutical composition and application thereof in preparation of a fluorescent probe, a phototherapy drug, a drug for diagnosis and / or treatment of cancer, and stimulus-responsive drug release. The compound provided by the application can accumulate at a tumor site, and can realize aggregation structure conversion and optical performance regulation by responding to a unique redox stimulus of a tumor microenvironment, realize precise photothermal / photodynamic combined treatment of the tumor in an aggregated state under irradiation of a specific excitation wavelength, and realize long-acting fluorescence imaging of a low background at the tumor after disaggregation of the aggregation. The tumor treatment effect is good, the trauma is small, the fluorescence imaging precision is high, the time is long, the biological safety is excellent, and diagnosis and treatment integration at the tumor site is realized.

The invention relates to iheyamine A spiro-structure derivatives I-1-I-16, a preparation method of the iheyamine A spiro-structure derivatives I-1-I-16 and application of the iheyamine A spiro-structure derivatives I-1-I-16 in The invention provides a series of iheyamine A spiro structure derivatives, develops an efficient synthesis method of the compounds, discovers the plant virus and plant pathogen resisting activity of the compounds, and lays a foundation for synthesis and biological activity research of the bisindole compounds. The iheyamine A spiro-structure derivatives I-1-I-16 provided by the invention have anti-plant virus activity, can inhibit tobacco mosaic virus, and meanwhile, the compounds show broad-spectrum anti-plant germ activity.

The invention discloses aralia bisindole alkaloid as well as a preparation method and application of the aralia bisindole alkaloid. The prepared aralia plant extract contains at least one of bisindole alkaloids Z-1-Z-21, monomer extraction and cell and animal experiment verification show that the bisindole alkaloid compound can protect nerve cell injury caused by glutamic acid, can improve the epilepsy state and prolong the epilepsy incubation period in an animal model, and can be used for preparing a medicine for treating the epilepsy. The cell arrangement in the brain sea horse area of the epilepsy mouse is improved; the neuron deformation is reduced. In addition, the series of bisindole alkaloid compounds have chemical structure types different from those of existing epilepsy treatment targeted drugs, and have wide application prospects in preparation of novel epilepsy treatment drugs.

The application discloses a preparation method of a 3,3'-bisindolylmethane compound. The method comprises the following steps: carrying out heteroarylation reaction of N-methyl indole compound and indole phosphonium salt in a solvent at 25-100 DEG C under the promotion of water; quenching the reaction; and extracting, washing, drying and concentrating the reaction product to obtain a crude product; and purifying the crude product to obtain the 3,3'-bisindolylmethane compound. The preparation method has the characteristics of mild reaction condition, good functional group tolerance, simple post-treatment, green step, low pollution and high economic benefit.

The invention provides an asymmetric preparation method of bisindole alkaloid (S)-6 ''-Debromohaamacanthin A. The method comprises the following steps: carrying out ester group reduction reaction on a compound 1 and lithium aluminum hydride to obtain a compound 2; carrying out azide substitution reaction on the compound 2, 1, 8-diazabicyclo [5.4. 0] undec-7-ene and diphenyl azide phosphate to obtain a compound 3; performing hydrolysis reaction on the compound 2 and a hydrochloric acid solution to obtain a compound 4; the preparation method comprises the following steps: mixing 6-bromoindole with oxalyl chloride to obtain an acyl chloride compound reaction solution; then carrying out acyl chloride substitution reaction on the compound 4, an acyl chloride compound reaction solution and triethylamine to obtain a compound 5; and carrying out Staudinger reduction reaction on the compound 5 and triphenylphosphine, so as to obtain the bisindole alkaloid (S)-6 ''-Debromohaamacanthin A. The invention further discloses a preparation method of the bisindole alkaloid (S)-6''-Debromohaamacanthin A. The invention further provides application, and the target product is used for preparing anti-tumor drugs. The synthetic route is unique in design, mild in reaction condition, high in catalytic efficiency, short in route, few in side reaction and simple and convenient to operate. According to the method, the problems that the source of the natural product (S)-6 ''-Debromohaamacanthin A is limited and the extraction rate is low can be solved.

The application discloses a preparation method of a bisindole methane type alkaloid and derivatives thereof by using a recyclable photocatalyst, and comprises the following steps: dissolving the photocatalyst in acetonitrile, adding aniline derivatives, indole compounds and organic acids in a molar ratio of 1:(2-3):(2-3), and irradiating under sunlight, a white light, a single wavelength 456nm or 427nm blue light source in an air or oxygen atmosphere, maintaining room temperature for 0.5-6h to obtain the bisindole methane type alkaloid and derivatives thereof; compared with the prior art, the application has the advantages of mild reaction conditions, reaction under sunlight in air, easy availability of the photocatalyst which can be recycled and used repeatedly, environmental protection of the solvent, high reaction yield, low cost of raw materials and simple operation.

The invention discloses a synthetic method of a natural product Racemosin B, and belongs to the field of organic synthesis. The method comprises the following steps: by taking indole as a raw material, carrying out an iodination reaction and an N-H protection reaction to obtain an iodinated indole compound 2, then carrying out a coupling reaction on the iodinated indole compound 2 and methyl acrylate under the synergistic catalysis of palladium / norbornene to obtain a 2, 3 '-bisindole compound 3, and then carrying out a ring closing and deprotection one-pot reaction under an iodine-mediated illumination reaction to generate the racemosin B. The method has the advantages of easily available raw materials, low price, unique and novel route design, short steps, mild reaction conditions and simple operation.

This invention relates to a thiophene-containing bisindolemethane-type α-glucosidase inhibitor, its preparation method, and its application, belonging to the field of glucosidase inhibitor preparation technology. Specifically, this invention discloses a thiophene-containing bisindolemethane-type α-glucosidase inhibitor, its preparation method, and its application. The method involves synthesizing a 3,3'-bisindolemethane compound through photo-oxidation and reduction of nitrohaloalkanes under blue light irradiation. Bromonitromethane participates in the reaction as a methylene precursor. The preparation process uses clean energy and yields a good yield of the 3,3'-bisindolemethane compound under mild conditions. Preliminary activity tests demonstrate that the bisindolemethane-type compound prepared by this invention has a significant inhibitory effect on α-glucosidase and can be used as a lead candidate for developing novel α-glucosidase inhibitors.