102991-38-8

Basic information

• Product Name: 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid
• Synonyms: DL-1,2,3,4-Tetrahydronorharmane-1-carboxylic acid
• CAS NO: 102991-38-8
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 0
• Mol File: 102991-38-8.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid(102991-38-8)
• EPA Substance Registry System: 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid(102991-38-8)

Safety Data

• Hazardous Substances Data: 102991-38-8(Hazardous Substances Data)

Usage

General Description

2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid is a chemical compound with a complex molecular structure. It belongs to the class of carboline alkaloids and is derived from the tetrahydrocarboline alkaloid family. 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid has been found to possess a variety of biological activities, including antioxidant, anti-inflammatory, and neuroprotective properties. It is also known to have potential therapeutic effects in treating neurodegenerative diseases such as Alzheimer's and Parkinson's. Additionally, 2,3,4,9-Tetrahydro-1H-b-carboline-1-carboxylic acid has been studied for its potential as an anti-cancer agent and its ability to modulate the immune system. Overall, this chemical compound shows promise for various medical and pharmaceutical applications.

Upstream product

• 61-54-1 tryptamine 
• 298-12-4 Glyoxilic acid 
• 6649-92-9 ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate 
• 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 
• 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 
• 17337-22-3 1-(hydroxymethyl)-β-carboline 
• 47064-53-9 2,3,4,9-Tetrahydro-2-(2-phenylmethyl)-1H-pyrido<3,4-b>indole 
• 153874-43-2 benzyl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate 

Relevant articles and documents

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.

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.

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

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.