6678-86-0

Usage

Uses

Used in Pharmaceutical Research:
1-Ethyl-2,3,4,9-tetrahydro-1H-beta-carboline is used as a research compound for its potential psychotropic effects. It is studied for its interaction with neurotransmitter systems in the brain, which may contribute to its psychotropic properties.
Used in Neurotransmitter System Studies:
Norharmane is used as a research tool to investigate its interaction with neurotransmitter systems, which could provide insights into its potential effects on the central nervous system and its role in neurological disorders.
Used in Cancer Research:
1-Ethyl-2,3,4,9-tetrahydro-1H-beta-carboline is used in studies exploring its potential role in the formation of DNA adducts. Understanding its impact on DNA adduct formation may have implications for cancer development and prevention strategies.
Used in Toxicology and Metabolism Studies:
Norharmane is utilized in toxicology research to examine its metabolic pathways and potential toxic effects on the human body, particularly in relation to its presence in tobacco and coffee.
Used in Analytical Chemistry:
1-Ethyl-2,3,4,9-tetrahydro-1H-beta-carboline can be used as a reference compound in analytical chemistry for the development and validation of methods for the detection and quantification of beta-carboline alkaloids in various matrices, such as plant extracts and biological samples.

InChI:InChI=1/C13H16N2/c1-2-11-13-10(7-8-14-11)9-5-3-4-6-12(9)15-13/h3-6,11,14-15H,2,7-8H2,1H3

Upstream product

• 343-94-2 tryptamine hydochloride 
• 123-38-6 propionaldehyde 
• 65601-07-2 1-Ethyl-4,9-dihydro-3H-pyrido<3,4-b>indole 
• 61-54-1 tryptamine 
• 123-72-8 butyraldehyde 

Downstream Products

• 1373764-81-8 1-ethyl-N-phenylacetyl-1,3,4,9-tetrahydro-β-carboline 
• 20127-61-1 1-ethyl-9H-β-carboline 
• 26585-14-8 crenatine 
• 75314-80-6 2-Benzoyl-1-ethyl-1,2,3,9-tetrahydro-β-carbolin-4-one 
• 75304-07-3 N-[2-(2-Propionyl-1H-indol-3-yl)-ethyl]-benzamide 
• 75304-06-2 1-ethyl-2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 

Relevant academic research and scientific papers

TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: Facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline

Multi-reactive centered reagents are beneficial in chemical synthesis due to their advantage of minimal material utilization and formation of less by-products. Trichloroisocyanuric acid (TCCA), a reagent with three reactive centers, was employed in the synthesis of spirooxindoles through the oxidative rearrangement of various N-protected tetrahydro-β-carbolines. In this protocol, low equivalents of TCCA were required to access spirooxindoles (up to 99% yield) with a wide substrate scope. Furthermore, the applicability and robustness of this protocol were proven for the gram-scale total synthesis of natural alkaloids such as (±)-coerulescine (1) and (±)-horsfiline (2) in excellent yields.

Candida antarctica lipase B catalysed kinetic resolution of 1,2,3,4-tetrahydro-?-carbolines: Substrate specificity

In the frame of substrate specificity, CAL-B-catalysed asymmetric N-alkoxycarbonylations of 1-substituted tetrahydro-?-carbolines (Me, Et, Pr, iPr) have been studied. High enantioselectivities (>200) were observed, when alkoxycarbonylation of racemic compounds (±)-1,3,5,7 were performed in DIPE in the presence of phenyl allyl carbonate and Et3N at 60 °C using ultrasound shaking method. The reaction time increased considerably with increasing substituent size on C1; however, the isopropyl-substituted compound proved to be too bulky for the optimum activity of CAL-B. The (R)-carbamate enantiomers were hydrolysed using Pd2(dba)3.CHCl3 and the enantiomers of the free amines were obtained with excellent ee (>99%).

Cu-catalyzed mild and efficient oxidation of THβCs using air: Application in practical total syntheses of perlolyrine and flazin

A mild, efficient and environmentally benign method for synthesis of aromatic β-carbolines via Cu(ii)-catalyzed oxidation of 1,2,3,4-tetrahydro-β-carbolines (THβCs) was developed, in which air (O2) was used as the clean oxidant. This method has advantages such as environmentally friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.

AGENTS FOR DIFFERENTIATING STEM CELLS AND TREATING CANCER

The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.

Oxidative Rearrangement Coupling Reaction for the Functionalization of Tetrahydro-β-carbolines with Aromatic Amines

The observation of an unexpected oxidative rearrangement coupling reaction led to the development of a novel method for the efficient functionalization of tetrahydro-β-carbolines (THβCs). The treatment of THβCs with photogenerated singlet oxygen (1O2) afforded unstable dioxetanes, which underwent further transformation to form new bonds in the presence of trifluoroacetic acid. This operationally simple protocol exhibits broad functional-group tolerance and is suitable for the late-stage functionalization of complex druglike molecules.

Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives

Synthesis of 13 different tetrahydro-β-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and l-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of α-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-β-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products.

Asymmetric Transfer Hydrogenation of Imines in Water by Varying the Ratio of Formic Acid to Triethylamine

Asymmetric transfer hydrogenation (ATH) of imines has been performed with variation in formic acid (F) and triethylamine (T) molar ratios in water. The F/T ratio is shown to affect both the reduction rate and enantioselectivity, with the optimum ratio being 1.1 in the ATH of imines with the Rh-(1S,2S)-TsDPEN catalyst. Use of methanol as a cosolvent enhanced reduction activity. A variety of imine substrates have been reduced, affording high yields (94-98%) and good to excellent enantioselectivities (89-98%). In comparison with the common azeotropic F-T system, the reduction with 1.1/1 F/T is faster.

Synthesis and biological evaluation of novel tetrahydro-β-carboline derivatives as antitumor growth and metastasis agents through inhibiting the transforming growth factor-β signaling pathway

The transforming growth factor beta (TGFβ) signaling cascade is considered as one of the pivotal oncogenic pathways in most advanced cancers. Inhibition of the TGFβ signaling pathway by specific antagonists, neutralizing antibodies, or small molecules is considered as an effective strategy for the treatment of tumor growth and metastasis. Here we demonstrated the identification of a series of tetrahydro-β-carboline derivatives from virtual screening which potentially inhibit the TGFβ signaling pathway. Optimization of the initial hit compound 2-benzoyl-1,3,4,9-tetrahydro-β- carboline (8a) through substitution at different positions to define the structure-activity relationship resulted in the discovery of potent inhibitors of the TGFβ signaling pathway. Among them, compound 8d, one of the tested compounds, not only showed potent inhibition of lung cancer cell proliferation and migration in vitro but also strongly suppressed growth of lung cancer and breast cancer in vivo.

Pictet-spengler reaction using ion-exchange resin as a catalyst and support for 'catch and release' purification

The Pictet-Spengler reaction between tryptamine and aldehydes was catalyzed by Dowex 50W-X4 acidic ion-exchange resin. The products were obtained from the resin in high purity by 'catch and release' without the need for separate chromatographic purification.

Biocatalytic asymmetric formation of tetrahydro-β-carbolines

Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-carbon bond and a new stereogenic center. Strictosidine contains a tetrahydro-β-carboline moiety - an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals. Stereoselective methods to produce tetrahydro-β-carboline enantiomers are greatly valued. We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-β-carbolines via a Pictet-Spengler reaction. This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-β-carbolines.