17071-83-9

Upstream product

• 864953-83-3 1-phenylsulfanyl-2-(toluene-4-sulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 1044148-61-9 (R)-2,5-dihydro-2-phenyl-1-tosyl-1H-pyrrole 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-52-7 benzaldehyde 
• 86658-78-8 N-tosyl tryptamine 

Downstream Products

• 16765-79-0 1-phenyl-9H-pyrido[3,4-b]indole 
• 10022-79-4 1-phenyl-4,9-dihydro-3H-β-carboline 

Relevant academic research and scientific papers

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.).

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer

Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.

Cyclometalated beta-carboline ruthenium complex and preparation method and application thereof

The invention relates to the technical field of antitumor drugs and concretely discloses a cyclometalated beta-carboline ruthenium complex and a preparation method and application thereof. The ruthenium complex takes 1-phenyl-9H-pyrido[3,4-b] indole as a main ligand, and takes 2,2-bipyridyl or 4,4-dimethyl-2,2 bipyridyl as an ancillary ligand. The ruthenium complex has a very excellent anti-tumor effect and has more excellent activity against liver cancer, breast cancer, lung cancer and cervical cancer cell lines than cis-platinum and similar polypyridine carboline ruthenium complexes.

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.

Mild and efficient syntheses of 1-aryl-3,4-dihydroisoquinolines and 1-aryl-3,4-dihydro-β-carbolines via regiospecific β-eliminations of the corresponding N-tosyl-1,2,3,4-tetrahydroisoquinolines and N-tosyl-1,2,3,4-tetrahydro-β-carbolines

(Chemical Equation Presented) Treatment of N-tosyl-1-aryl-1,2,3,4- tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-β-carbolines with a strong base such as NaOH or KOH at 70 °C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-β- carbolines in good yields via mild and regiospecific β-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 °C. Copyright Taylor & Francis Group, LLC.

Efficient and practical one-pot conversions of n- tosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro-β- carbolines into β-carbolines through tandem β-elimination and aromatization

An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines in good to high yields. Both one-pot conversions occurred through tandem β-elimination and aromatization. An efficient method for conversions ofN-tosyltetrahydroisoquinolines (N-tosyl-THIQs) and N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into isoquinolines and β-carbolines is described. Treatment ofN-tosyl-THIQs or N-tosyl-THBCs with base affords dihydroisoquinolines or dihydro-β- carbolines. These can be oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines. Copyright

A novel access to tetrahydro-β-carbolines via one-pot hydroformylation/fischer indole synthesis: Rearrangement of 3,3- spiroindoleninium cations

(Chemical Equation Presented) The two component one-pot hydroformylation/Fischer indole synthesis sequence of 2,5 dihydropyrroles and phenyl hydrazines allows a facile and convenient access to tetrahydro-β- carbolines in moderate to good yields.

1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals

(Chemical Equation Presented) The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substitu