121998-74-1

Upstream product

• 343-94-2 tryptamine hydochloride 
• 4569-82-8 2-phenyl-1,3-thiazolidine 
• 61-54-1 tryptamine 
• 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 
• 88939-53-1 3,4,4-Trimethyl-2-phenyl-1-(toluene-4-sulfonyl)-imidazolidine 
• 780-21-2 N-(4-chlorobenzylidene)aniline 

Downstream Products

• 1031995-75-1 C₂₆H₂₄N₂O 
• 4894-26-2 3,4-dihydro-β-carboline 
• 16765-79-0 1-phenyl-9H-pyrido[3,4-b]indole 
• 13896-21-4 2-(1-phenyl-2,3,4,9-tetrahydro-1H-beta-carbolin-2-yl)ethanol 
• 65048-57-9 2-N-benzyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 

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

Selectivity-tunable oxidation of tetrahydro-β-carboline over an OMS-2 composite catalyst: preparation and catalytic performance

Controlling the reaction selectivity of organic transformations without losing high conversion is always a challenge in catalytic processes. In this work, a H3PO4·12WO3/OMS-2 nanocomposite catalyst ([PW]-OMS-2) was prepared through the oxidation of a Mn(ii) salt with sodium phosphotungstate by KMnO4. Comprehensive characterization indicates that different Mn2+precursors significantly affected the crystalline phase and morphology of the as-synthesized catalysts and only MnSO4·H2O as the precursor could lead to a cryptomelane phase. Moreover, [PW]-OMS-2 demonstrated excellent catalytic activity toward aerobic oxidative dehydrogenation of tetrahydro-β-carbolines due to mixed crystalline phases, enhanced surface areas, rich surface oxygen vacancies and labile lattice oxygen species. In particular, β-carbolines and 3,4-dihydro-β-carbolines could be obtained from tetrahydro-β-carbolines with very high selectivity (up to 99%) over [PW]-OMS-2viatuning the reaction solvent and temperature. Under the present catalytic system, scalable synthesis of a β-carboline was achieved and the composite catalyst showed good stability and recyclability. This work not only clarified the structure-activity relationship of the catalyst, but also provided a practical pathway to achieve flexible, controllable synthesis of functional N-heterocycles.