121998-74-1

Upstream product

• 343-94-2 tryptamine hydochloride 
• 16979-93-4 N-benzylidene-2-(1H-indol-3-yl)ethylamine 
• 20515-61-1 2-phenyl-4,4-dimethyloxazolidine 
• 61-54-1 tryptamine 
• 4569-82-8 2-phenyl-1,3-thiazolidine 
• 1630-62-2 3-methyl-2-phenyl-oxazolidine 
• 17762-72-0 2-phenyl-tetrahydro-(2H)-1,3-oxazine 
• 31230-83-8 2-Phenylbenzothiazolin 
• 16192-33-9 3-Methyl-2-phenyl-2,3-dihydrobenzothiazoline 
• 96625-02-4 C₃H₄SN(n-C₄H₉)HC₆H₅ 
• 67189-36-0 N-acetyl-2-phenyl-1,3-thiazolidine 
• 16285-78-2 2,3-Diphenyl-1,3-oxazolidine 
• 538-51-2 benzylidene phenylamine 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 

Downstream Products

• 3574-01-4 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole hydrochloride 
• 114896-50-3 2-(ethoxycarbonyl)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole 
• 114896-46-7 2-(chloroacetyl)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indole 
• 16765-79-0 1-phenyl-9H-pyrido[3,4-b]indole 
• 10022-79-4 1-phenyl-4,9-dihydro-3H-β-carboline 
• 65048-57-9 2-N-benzyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 4894-26-2 3,4-dihydro-β-carboline 
• 1450994-45-2 C₂₄H₁₉Br₂N₃ 

Relevant academic research and scientific papers

Pictet-Spengler reaction of nitrones and imines catalyzed by Yb(OTf)3-TMSCI

The Pictet-Spengler reaction of nitrones and imines prepared from N-hydroxytryptamine and tryptamine gave the corresponding tetrahydro-β-carbolines in excellent yields in the presence of Yb(OTf)3-TMSCl in a mixture of CH2Cl2/su

Iodine-catalyzed highly effective pictet-spengler condensation: An efficient synthesis of tetrahydro-β-carbolines

Molecular iodine was found to be an efficient catalyst for the two-component Pictet-Spengler condensation of tryptamine with aldehydes, which leads to the formation of tetrahydro-β-carbolines in high yields. Copyright Taylor & Francis Group, LLC.

Catalytic Oxidative Coupling Cyclization for Construction of Benzofuroindolenines under Mild Reaction Conditions

We describe iron-catalyzed oxidative coupling cyclization of tetrahydrocarbazoles or THβCs or THγCs to form benzofuroindolenines as fused polycyclic indoles. This mild, efficient and simple approach afforded a library of more than 52 complex compounds across a range of substrate classes with good to excellent yields. (Figure presented.).

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.

Observations on the Pictet-Spengler Synthesis of 1,2,3,4-Tetrahydro-β-carbolines

The Pictet-Spengler cyclisation of the benzylideneimine of tryptophan methyl ester in xylene, contrary to literature reports, occurs extremely slowly, if at all, in the absence of acids.The cyclisation is Bronsted acid catalysed and the rate of cyclisatio

Synthesis, characterization, cellular uptake and apoptosis-inducing properties of two highly cytotoxic cyclometalated ruthenium(II) β-carboline complexes

Two new cyclometalated Ru(II) complexes of the general formula [Ru(N-N)2(1-Ph-βC)](PF6), where N–N = 4,4′-dimethyl-2,2′-bipyridine (dmb, Ru1), 2,2′-bipyridine (bpy, Ru2), and 1-Ph-βC (1-phenyl-9H-pyrido[3,4-b]indole) is a β-carboline alkaloids derivatives, have been synthesized and characterized. The in vitro cytotoxicities, cellular uptake and localization, cell cycle arrest and apoptosis-inducing mechanisms of these complexes have been extensively explored by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, inductively coupled plasma mass spectrometry (ICP-MS), flow cytometry, comet assay, inverted fluorescence microscope as well as western blotting experimental techniques. Notably, Ru1 and Ru2 exhibit potent antiproliferative activities against selected human cancer cell lines with IC50 values lower than those of cisplatin and other non-cyclometalated Ru(II) β-carboline complexes. The cellular uptake and localization exhibit that these complexes can accumulate in the cell nuclei. Further antitumor mechanism studies show that Ru1 and Ru2 can cause cell cycle arrest in the G0/G1 phase by regulating cell cycle relative proteins and induce apoptosis through mitochondrial dysfunction, reactive oxygen species (ROS) accumulation and ROS-mediated DNA damage.

Alkylation of 3,4-Dihydro-β-carboline

Alkylation of 3,4-dihydro-β-carboline has been accomplished with organo-copper and -lithium reagents by activation of BF3*OEt2 or trimethylsilyl trifluoromethanesulphonate.

Structural simplification of evodiamine: Discovery of novel tetrahydro-β-carboline derivatives as potent antitumor agents

Natural products (NPs) have played a crucial role in the discovery and development of antitumor drugs. However, the high structural complexity of NPs generally results in unfavorable physicochemical profiles and poor drug-likeness. A powerful strategy to tackle this obstacle is the structural simplification of NPs by truncating nonessential structures. Herein, a series of tetrahydro-β-carboline derivatives were designed by elimination of the D ring of NP evodiamine. Structure-activity relationship studies led to the discovery of compound 45, which displayed highly potent antitumor activity against all the tested cancer cell lines and excellent in vivo antitumor activity in the HCT116 xenograft model with low toxicity. Further mechanistic research indicated that compound 45 acted by dual Top1/2 inhibition and induced caspase-dependent cell apoptosis coupled with G2/M cell cycle arrest. This proof-of-concept study validated the effectiveness of structural simplification in NP-based drug development, discovered compound 45 as a potent antitumor lead compound and enriched the structure–activity relationships of evodiamine.

Metal-Free Access to (Spirocyclic)Tetrahydro-β-carbolines in Water Using an Ion-Pair as a Superacidic Precatalyst

The unprecedented triarylcarbonium ion-pair-catalyzed Pictet-Spengler reaction of tryptamines with aromatic aldehydes and cyclic ketones in water was disclosed. Under metal-free conditions, diverse tetrahydro-β-carbolines and spirocyclic tetrahydro-β-carb

Synthesis of crystalline tetrahydro-beta-carboline

The present invention relates to a method for preparing a tetrahydro-beta-carboline compound, which comprises a step of preparing a tetrahydro-beta-caboline compound by reacting a tryptamine compound and an aldehyde in an aqueous solution using a reaction accelerator containing a divalent acid. Accordingly, the method for preparing a tetrahydro-beta-carboline compound according to the present invention is an eco-friendly synthetic method that does not use an explosive organic solvent, but uses water as a solvent and tartaric acid which is a natural product as a reaction accelerator, thereby causing no environmental pollution; and requiring no separation process in addition to a simple filtering process since final products are crystals. Therefore, the method for preparing a tetrahydro-beta-carboline compound can be carried out in an industrially very simple and suitable process.