6649-91-8

Usage

Uses

Used in Pharmaceutical Research:
1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-1-CARBOXYLIC ACID is used as a research compound for studying its potential therapeutic effects and mechanisms of action in the context of neurodegenerative diseases.
Used in Neurodegenerative Disease Research:
1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-1-CARBOXYLIC ACID is used as a tool in the investigation of the molecular and cellular processes involved in neurodegenerative diseases, such as Alzheimer's, Parkinson's, and Huntington's diseases. Its study may contribute to the development of novel therapeutic strategies and interventions for these conditions.

InChI:InChI=1/C12H12N2O2/c15-12(16)11-10-8(5-6-13-11)7-3-1-2-4-9(7)14-10/h1-4,11,13-14H,5-6H2,(H,15,16)

Upstream product

• 6649-92-9 ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate 
• 61-54-1 tryptamine 
• 298-12-4 Glyoxilic acid 
• 343-94-2 tryptamine hydochloride 
• 6000-59-5 glyoxalic acid monohydrate 

Downstream Products

• 127661-45-4 methyl 2,3,4,9-tetrahydro-1H-pyrido [3,4-b]indole-1-carboxylate 
• 1262779-54-3 C₁₉H₁₅BrN₂O₃ 
• 1262779-60-1 C₁₉H₁₄F₂N₂O₃ 
• 1262779-53-2 C₂₀H₁₈N₂O₄ 
• 1262779-55-4 C₁₉H₁₄F₂N₂O₃ 
• 1161934-12-8 2-(4-fluorobenzoyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid 
• 128019-27-2 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid 
• 38940-60-2 9H-pyrido[3,4-b]indole-1-carboxamide 
• 88704-44-3 eudistomin H 
• 88704-45-4 eudistomin I 
• 101716-70-5 2-benzoyl-2,3,4,9-tetrahydro-β-carbolin-1-one 
• 3464-66-2 methyl 9H-pyrido[3,4-b]indole-1-carboxylate 
• 16502-01-5 tetrahydrobetacarboline 
• 155346-24-0 2-phenyl-5,6,11,11b-tetrahydro-1H-imidazo<1',5':1,2>pyrido<3,4-b>indole-1,3(2H)-dione 

Relevant academic research and scientific papers

Pityriacitrin alkaloid derivative containing acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative

The invention discloses a pityriacitrin alkaloid derivative containing an acylthiourea structure as well as a preparation method and application of the pityriacitrin alkaloid derivative, and relates to a biocide of the pityriacitrin alkaloid derivative co

pityriacitrin Alkaloid derivative containing acylhydrazone structure, and preparation method and application thereof

The pityriacitrin alkaloid derivative containing the acylhydrazone structure and a preparation method and application thereof relate to a biocide containing β - carboline and 1-position of pityriacitrin alkaloids containing an acylhydrazone structure, pit

Peganumine A alkaloid structure simplifier and application thereof

The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.

Discovery and preliminary mechanism of 1-carbamoyl β-carbolines as new antifungal candidates

Natural β-carboline alkaloids are ideal models for the discovery of pharmaceutically important entities. Various 1-substituted β-carbolines were synthesized from commercially inexpensive tryptophan and demonstrated significant in vitro antifungal activity against G. graminis. Significantly, compound 4m (EC50 = 0.45 μM) with carboxamide at 1-position displayed the best efficacy and nearly 20 folds enhancement in antifungal potential compared to Silthiopham (EC50 = 8.95 μM). Moreover, compounds 6, 7, and 4i exhibited excellent in vitro antifungal activities and in vivo protective and curative activities against B. cinerea and F. graminearum. Preliminary mechanism studies revealed that compound 4m caused reactive oxygen species accumulation, cell membrane destruction, and deregulation of histone acetylation. These findings indicated that 1-carbamoyl β-carboline can be selected as a promising model for the discovery of novel and broad-spectrum fungicide candidates.

First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine

The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine.

A pure red luminescent β-carboline-substituted biphenylmethyl radical: Photophysics, stability and OLEDs

Luminescent radicals, whose emission comes from the doublet exited state, have potential application in the field of organic optoelectronics. However, few radicals show luminescence at room temperature. Herein, a new pure red-emissive biphenyl-type (N-pyrido[3,4-b]indolyl)bis(2,4,6-trichlorophenyl)methyl radical (PyID-BTM) is designed and synthesized, in which the carbazole moiety of CzBTM (a previously reported biphenylmethyl radical by our group) is successfully replaced by β-carboline. Its photophysical properties, including the ground and excited states, and the radiative and non-radiative processes are systematically investigated. The photoluminescence quantum efficiency ( = 19.5%) of PyID-BTM is ten times higher than that of CzBTM ( = 2.0%) in cyclohexane. The crystal structure, magnetic properties, photostability and electroluminescence performance of PyID-BTM are studied. An optimized OLED device using PyID-BTM as an emissive dopant showed pure red emission with CIE coordinates of (0.649,0.317) and a maximum EQE of 2.8%, and the formation ratio of doublet excitons was up to 70%. This study provides a new approach for designing high-performance luminescence biphenylmethyl radicals for applications in organic electroluminescence.

Spiro[pyrrolidine-3, 3′-oxindoles] and their indoline analogues as new 5-HT6 receptor chemotypes

Synthetic derivatives of spiro[pyrrolidinyl-3, 3′-oxindole] alkaloids (coerulescine analogues) were investigated as new ligands for aminergic G-protein coupled receptors (GPCRs). The chemical starting point 2′-phenylspiro[indoline-3, 3′-pyrrolidin]-2-one scaffold was identified by virtual fragment screening utilizing ligand- and structure based methods. As a part of the hit-to-lead optimization a structure-activity relationship analysis was performed to explore the differently substituted 2′-phenyl-derivatives, introducing the phenylsulphonyl pharmacophore and examining the corresponding reduced spiro[pyrrolidine-3, 3′-indoline] scaffold. The optimization process led to ligands with submicromolar affinities towards the 5-HT6 receptor that might serve as viable leads for further optimization.

Novel indolizino[8,7-b]indole hybrids as anti-small cell lung cancer agents: Regioselective modulation of topoisomerase II inhibitory and DNA crosslinking activities

A novel series of bis(hydroxymethyl)indolizino[8,7-b]indole hybrids composed of β-carboline (topoisomerase I/II inhibition) and bis(hydroxymethyl)pyrrole (DNA cross-linking) are synthesized for antitumor evaluation. Of tumor cell lines tested, small cell

Dynamic Kinetic Resolution of Ethyl 1,2,3,4-Tetrahydro-β-carboline-1-carboxylate: Use of Different Hydrolases for Stereocomplementary Processes

Both enantiomers of 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid have been prepared by dynamic kinetic resolution of the corresponding ethyl ester (±)-1. CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98 % ee and 90 % yield in 20 min. The hydrolysis with Alcalase in borate buffer (pH 8.0, 30 °C) showed S selectivity and the product (S)-2·HCl was obtained with 60 % ee and 66 % yield in 45 h. The absolute configuration of (S)-2 was determined by TDDFT electronic circular dichroism and optical rotation calculations.

Diversity-oriented reconstruction of primitive diketopiperazine-fused tetrahydro-β-carboline ring systems via Pictet-Spengler/Ugi-4CR/deprotection-cyclization reactions

An expedient construction of tetrahydro-β-carbolinediketopiperazine ring systems, which are present in various indole alkaloids, is documented. The synthetic strategy proceeds through a Pictet-Spengler reaction followed by an Ugi-4CR and deprotection-cyclization reactions. This is the first report of a Pre-Ugi multicomponent reaction modification using 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid as the acidic partner. This novel approach provides highly diverse reconstructions of novel tetrahydro-β-carbolinediketopiperazine derivatives, which can also be used as privileged structures in medicinal chemistry.