102991-38-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid is used as a therapeutic agent for its neuroprotective properties, particularly for the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. Its antioxidant and anti-inflammatory activities contribute to its potential in managing these conditions.
Used in Oncology:
2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid is utilized as an anti-cancer agent, where its potential to modulate cellular processes involved in cancer development and progression is being explored. It may offer new avenues for cancer treatment by targeting specific pathways or mechanisms within cancer cells.
Used in Immunomodulation:
In the field of immunology, 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid is used as an immunomodulatory agent. Its ability to influence the immune system suggests applications in conditions where immune system regulation is required, such as autoimmune diseases or inflammatory conditions.
These uses highlight the diverse potential applications of 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid across different areas of medicine, underscoring the need for further research to fully understand and harness its capabilities.

Upstream product

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

Downstream Products

• 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 
• 58911-02-7 Tryptoline hydrochloride 
• 128019-27-2 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid 
• 1161934-12-8 2-(4-fluorobenzoyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid 
• 1262779-55-4 C₁₉H₁₄F₂N₂O₃ 
• 1262779-53-2 C₂₀H₁₈N₂O₄ 
• 1262779-60-1 C₁₉H₁₄F₂N₂O₃ 
• 1262779-54-3 C₁₉H₁₅BrN₂O₃ 
• 1174589-29-7 C₁₈H₁₄N₄O₃S 
• 1174589-30-0 C₁₉H₁₆N₄O₃S 
• 1309918-64-6 C₁₈H₁₃FN₄O₃S 

Relevant academic research and scientific papers

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.

An efficient route to 5-iodo-1-methylimidazole: Synthesis of xestomanzamine A

An efficient and practical route to C-5 functionalized N-methylated imidazoles is reported. 5-Iodo-1-methylimidazole was synthesized in four steps from imidazole, with complete regiospecificity, in 73% overall yield. The synthesis of xestomanzamine A, a marine natural product isolated in 1995 from an Okinawan sponge of Xestospongia sp., has been achieved using 5-iodo-1-methylimidazole in a modified Grignard reaction with a β-carboline ester moiety, in an overall yield of 59% based upon imidazole and 53% based upon tryptamine.

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.

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.

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.

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.

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.

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.