156 results about "Tryptamines" patented technology

The invention belongs to the medicinal field, and concretely relates to a use of a 8-nitrotryptanthrin compound as an IDO inhibitor. The 8-nitrotryptanthrin compound is a reversible IDO inhibitor, has an inhibition constant Ki of 0.054muM, has in-vitro and cell-based median effective inhibition concentrations IC50 of 0.103muM and 1.80*10<-5>muM respectively, and has an inhibition effectiveness obviously better than a present inhibitor 1-methyltryptophan (Ki of 34muM and IC50 of 340muM). 8-nitrotryptanthrin disclosed in the invention can effectively lower the abnormally-increasing IDO activity in a tumor animal model as the IDO inhibitor, and also has tumor treatment effects comprising tumor growth delaying, tumor volume reduction and in-vitro tumor cell killing. 8-nitrotryptanthrin disclosed in the invention has a wide application prospect, and can be used for treating serious diseases having the IDO mediated tryptophan metabolism approach pathology characteristics, such as cancers, the Alzheimer disease, tristimania, cataract and the like as the IDO inhibitor.

The invention relates to a novel tryptanthrin (indole[2,1-b] quinazoline-6,12-diketone) derivative, a synthetic method and a medicinal application thereof. A general structural formula is as follows (see the description). The novel tryptanthrin derivative is synthesized through biomimetic synthesis, the general chemical structural formula of the novel derivative is shown in Figure 1, wherein in the formula, R,R1,R2,R3 are halogen, nitro, amido, hydroxy, alkyl, alkoxy and aryl, R1is morpholine, piperidine, N-methylpiperidine, N-ethylpiperidine, isonipecotic acid, piperazine, 1-(2-pyridyl) piperazine, dimethylamine, diethylamine, 1-(2-ethoxy) piperazine and 1-(2-furoyl) piperazine, and an o-aminobenzoic acid derivative reacts with an indole quinone derivative in solvents of methylbenzene, methyl alcohol, ethyl alcohol, dichloromethane, isopropanol and the like, so as to prepare the novel tryptanthrin derivative. The novel tryptanthrin derivative which has a good inhibiting effect and a good antibacterial effect on cancer cells is preliminarily screened through an MTT experiment and an antibacterial experiment, and the medicine has pharmacological effects in the aspects of tumor resistance, antibiosis and inflammation diminishing.

The present invention relates to compositions comprising N,N-dimethyltryptamine, deuterated N,N-dimethyltryptamine and/or partially deuterated N,N-dimethyltryptamine. In particular, the present invention relates to compositions comprising a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more deuterated N,N-dimethyltryptamine compound selected from α,α-dideutero-N,N-dimethyltryptamine and α,α,β,β-tetradeutero-N,N-dimethyltryptamine. Additional and alternative compositions of the present invention comprise a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more partially deuterated N,N-dimethyltryptamine compound selected from α,β,β-trideutero-N,N-dimethyltryptamine, α,β-dideutero-N,N-dimethyltryptamine, and α-deutero-N,N-dimethyltryptamine. Methods of synthesising compositions of the present invention, and methods of use of presently described compositions in treating psychiatric or psychocognitive disorders, such as major depressive disorder, are also provided.

The present invention provides a tryptamine prodrug compound. A compound represented by the formula (I)

where each symbol is as described in the specification, or a salt or zwitterion thereof, is converted to an active which has 5HT2A receptor agonist activity, and is useful as an agent for the treatment of depression.

The invention discloses a method for synthesizing an optically active tetrahydro-beta-carboline derivative through the catalysis of chiral spirocyclic phosphoric acid. The method comprises the following steps of: reacting at the temperature of between 20 and 40 DEG C for 3 to 50 hours by taking Nb-alpha-naphthylmethyl tryptamine and aldehyde as raw materials, the chiral spirocyclic phosphoric acid as a catalyst and benzene as a reaction solvent in the presence of 4 angstrom molecular sieve powder under the protection of nitrogen, and performing column chromatographic purification and separation to obtain the optically active tetrahydro-beta-carboline derivative. Reaction conditions are mild, and the process is simple and convenient to operate; and the obtained optically active tetrahydro-beta-carboline derivative has high potential bioactivity, and can be used as an intermediate for pharmaceutical synthesis.

The invention discloses compounds represented by a general formula (I) shown in the description, wherein in the formula (I), A and B are respectively a six-membered cyclic compound containing D1, D2,D3 and D4 and a six-membered cyclic compound containing D5, D6, D7 and D8. The invention also disclose an indoleamine-2,3-dioxygenase and/or tryptophan-2,3-dioxygenase inhibitor containing the above compounds and the application of the compounds in preparation of medicaments for treating cancers. The compounds provided by the invention can effectively inhibit cell proliferation, and have good therapeutic effects on various diseases such as the cancers, significant therapeutic effects on breast cancer, cervical cancer, colon cancer, lung cancer, stomach cancer, rectal cancer, pancreatic cancer,brain cancer, skin cancer, oral cancer, prostate cancer, bone cancer, kidney cancer, ovarian cancer, bladder cancer, liver cancer, fallopian tube tumors, ovarian tumors, peritoneal tumors, stage IV melanoma, glioma, neuroblastoma, hepatocellular carcinoma, mastoid renal tumors, head and neck tumors, leukemia, lymphoma, myeloma and non-small cell lung cancers, and very broad application prospects.

Diazene-directed modular synthesis is described for the preparation Csp2-Csp3 and Csp3-Csp3 linkages where one or more stereogenic quaternary carbon centers are formed. The disclosed methods are directed to the preparation of compounds of Formula (I), or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, from compounds of Formula (II):

wherein R¹-R⁵ and q are as defined independently for each occurrence herein. A wide variety of compounds can be accessed in this manner, including oligocyclotryptamines, where the stereochemistry of each subunit is beneficially secured before fragment coupling.

The present invention discloses a method to recover and restore dendritic and synaptic neuron connections that have been degraded or destroyed by neurodegenerative diseases. In the present invention tryptamines are used to induce neuro plasticity and restore both dendritic density and synaptic connections of neurons in the brain. In the preferred embodiment LSD given in micro doses can induce dendritic and synaptic genesis in neuronal networks and improve the quality of life of people with neurodegenerative diseases such as Alzheimer's, Huntington's, Multiple Sclerosis, Parkinson's and Frontotemporal dementia.

Crystalline forms of 4-acetoxy-N,N-dimethyltryptamine (psilacetin), compositions containing that crystalline form, and their methods of use are disclosed. The crystalline forms of 4-acetoxy-N,N-dimethyltryptamine (psilacetin) according to the disclosure include crystalline 4-acetoxy-N,N-dimethyltryptammonium hydrofumarate, the fumarate salt of psilacetin, and/or crystalline bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate, and pharmaceutical compositions containing a crystalline form of psilacetin.

The invention discloses a novel tryptamine derivative. The novel tryptamine derivative is characterized in that the chemical structural formula of the novel tryptamine derivative is as shown in the specification. According to the invention, an intracerebral tryptamine hormone fragment with an anti-neuroinflammation effect and a non-steroidal anti-inflammatory drug salicylic acid and derivatives thereof are subjected to molecular combination; on one hand, COX effect can be inhibited; and on the other hand, the generation of iNOS and inflammatory factors and the activation of immune cells can beinhibited, and the occurrence and development of inflammations are jointly inhibited through multiple mechanisms. Meanwhile, carboxylic acid groups of salicylic acid non-steroidal anti-inflammatory drugs can be removed, so gastrointestinal side effects caused by acidity are reduced. On such a basis, a series of compounds are designed and synthesized; and enzyme inhibition tests, various immune cell tests and animal in-vivo experimental studies prove that the synthesized compounds have good anti-inflammatory and analgesic activity.

The invention discloses a chiral 3-indolyl-3,3'-disubstituted oxoindole compound and a preparation method thereof and belongs to the field of organic chemical synthesis; the preparation method comprises the following steps: dissolving 2-nitroindole (I) and 3-substituted oxindole (II) in an organic solvent, adding a chiral catalyst, carrying out a stirring reaction at 0-25 DEG C for 5-7 days, adding a solvent and an organic acid into the reaction system after the reaction is completed, continuously carrying out a reaction on the reaction mixed solution at 0-25 DEG C for 10-15 h, and carrying out separation and purification. According to the preparation method disclosed by the invention, through asymmetric dearomatization/heavy aromatization reaction of 2-nitroindole, the preparation of chiral 3-indolyl-3'-alkyl oxindole and 3-indolyl-3'-aryl oxindole derivatives is realized; the compound is a key synthetic intermediate of cyclic tryptamine alkaloid, and can provide more candidate molecules for research and development of new drugs and screening of drugs. The preparation method disclosed by the invention has the advantages of novelty, simplicity, simplicity in operation, mild reaction conditions, high yield, high stereoselectivity and the like.

Compounds of Formula (I): (I); wherein: R1 and R2 either the same or different, are H or linear or branched C1-C6 alkyl; R3=linear or branched C1-C6 alkyl; R4=halogen, and pharmaceutically acceptable salts thereof are useful as active ingredients in the preparation of medicaments used as ligands of the 5-HT6 and/or 5-HT7 serotoninergic receptors.

The invention discloses a 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound,a preparation method and applications thereof, wherein the structural general formula (I) of the compoundis defined in the specification, R1 is hydrogen atom, morpholinomethyl, piperazinomethyl or substituted piperazinomethyl, R2 is hydrogen atom, butyl, morpholine substituted alkyl, benzyl, substitutedbenzyl, tryptamine, substituted tryptamine or N,N-dimethylamino, R3 is-C(O)R4 or-SO2R5, R4 and R5 are alkyl (C3-C6 alkyl), cycloalkyl (3-6-membered ring), alkoxy or alkyl substituted amino, and n is 1, 2, 3 or 4. The compound of the invention has inhibition activity on breast cancer, prostate cancer and human neuroblastoma.

The invention provides an evodiamine derivative. The evodiamine derivative is prepared by taking an anthranilic acid compound and tryptamine as initial raw materials through a condensation reaction and a one-step ring closing reaction catalyzed by lewis acid. The evodiamine derivative prepared by the preparation method disclosed by the invention has dual inhibition effects on topoisomerase I/II, so a broad-spectrum anti-tumor effect is achieved. The derivative can induce apoptosis of cancer cells and retard proceeding to a G2/M period in a concentration-dependent manner, and has an effect of inhibiting invasion and migration of cancer cells in vitro. The derivative has a good tumor growth inhibition effect in a nude mouse transplantation tumor model, has no obvious toxicity at a cell level and an animal level, has good safety and can be applied to preparation of anti-tumor drugs.

The invention discloses an application of a tetrahydro-beta-carboline dimer derivative in the preparation of a medicine for preventing or treating Alzheimer's disease. The tetrahydro-beta-carboline dimer derivative is as shown in a structural formula I, which is described in the specification, L-tryptophan and tryptamine are used as raw materials; a tetrahydro-beta-carboline monomer is generated through a Picet-Spengler reaction and aldehyde cyclization, then a tetrahydro-beta-carboline dimer is generated through acyl chloride connection and a click chemical reaction, the synthesis steps are simple, the raw materials are easy to obtain, the yield is high, and the tetrahydro-beta-carboline dimer has remarkable inhibitory activity on butyrylcholine esterase and A[beta]1-42 aggregation. According to the neural protective effect under three AD models on cells, after the cells are independently treated by A[beta]1-42, H2O2 and OA, the survival rate of the cells is low, and apoptosis or necrosis of the cells occurs. The compounds 11, 12, 13, 17 and 19 are used for co-treatment, the compounds 11, 12, 13, 17 and 19 successfully block A[beta]1-42, H2O2 and OA induced cell death, and it is proved that the compounds 11, 12, 13, 17 and 19 have a remarkable neural protective effect.

The invention discloses a nitrogen-phosphorus efficient flame retardant containing p-hydroxybenzaldehyde and tryptamine structures, a preparation method and an application. The preparation method comprises the following steps: S1, adding p-hydroxybenzaldehyde and tryptamine into a solvent for reaction under the protection of nitrogen to obtain a p-hydroxybenzyltryptamine Schiff base solution; S2,adding 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide into the p-hydroxybenzyltryptamine Schiff base solution obtained in the step S1 for reaction to obtain a p-hydroxybenzyltryptamine phosphaphenanthrene solution; and S3, cooling the p-hydroxybenzyltryptamine phosphaphenanthrene solution obtained in the S2 to room temperature, adding deionized water to separate out a white solid, filtering,washing the white solid with deionized water for 2-3 times, and drying the white solid to obtain the nitrogen-phosphorus efficient flame retardant containing p-hydroxybenzaldehyde and tryptamine structures. The high polymer material prepared by the invention has good transparency.

The invention provides an indoleamine 2, 3-dioxygenase 2 inhibitor and application thereof, and particularly provides a formula-I compound or pharmaceutically-acceptable sodium thereof. The compound has excellent effects of inhibiting indoleamine 2, 3-dioxygenase 2 activity and resisting tumors. The invention further provides a drug composition containing the compound and application of the drug composition in resisting indoleamine 2, 3-dioxygenase.

The invention discloses a Eudistomins Y derivative with anti-tumor activity as well as a preparation method and application of the Eudistomins Y derivative. A tryptamine derivative (i) is used as a raw material and is subjected to a feeding reaction with acetophenone derivatives (ii), I2 and H2O2 to obtain a compound represented by a general formula (iii), and the compound represented by the general formula (iii) is subjected to a feeding reaction with R-X and K2CO3 according to the molar ratio of 1:(2-6):(2-6) to obtain a compound represented by a general formula (I). The invention provides the Eudistomins Y derivative represented by a general formula (I) and a medically acceptable salt thereof. The Eudistomins Y derivative has the antitumor activity, and is obviously superior to an Eudistomin Y1 prototype compound in the aspect of inhibiting tumor cell proliferation; compared with the non-fluorescence activity of a natural Eudistomins Y compound, the Eudistomins Y derivative represented by the general formula (I) provided by the invention has a fluorescence characteristic and can effectively trace the distribution of the Eudistomins Y derivative in cells and tissues.

Crystalline N-methyl tryptamine derivatives, compositions containing those crystalline forms and their methods of use are disclosed. The crystalline N-methyl tryptamine derivatives according to the invention include crystalline N-methyl-N-propyltryptamine (MPT), crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) and crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate).

The invention discloses an asymmetric synthesis method of chiral tryptanthrin beta hydroxy ester compounds. The method comprises following steps: tryptanthrin compounds and mono-alkyl malonate are taken as raw materials, metal and a chiral ligand which are taken as catalysts are subjected to a direct sufficient reaction in an organic solvent, a reaction solution is separated and purified after thereaction is ended, and the chiral tryptanthrin beta hydroxy ester compounds with high stereoselectivity, namely, Phaitanthrin B-series pharmaceutical molecules as natural products, are obtained. Themethod has main beneficial effects as follows: 1, operation is simple; 2, cost is low; 3, reaction yield is high; 4, stereoselectivity is high, thereby having higher fundamental research value and social and economic benefits.