6649-77-0

Upstream product

• 61-54-1 tryptamine 
• 201230-82-2 carbon monoxide 
• 6335-03-1 2-(2-methyl-allyl)-isoindole-1,3-dione 
• 590-86-3 isovaleraldehyde 
• 343-94-2 tryptamine hydochloride 
• 81535-31-1 2-<(tert-butylimino)methyl>-1,2,3,4-tetrahydro-β-carboline 
• 81535-40-2 1-Isobutyl-9-methoxymethyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 16502-01-5 tetrahydrobetacarboline 
• 128593-36-2 1-isobutyl-4,9-dihydro-3H-β-carboline 
• 81535-41-3 (1-Isobutyl-1,2,3,4-tetrahydro-β-carbolin-9-yl)-methanol 
• 78-77-3 Isobutyl bromide 
• 81535-36-6 tert-Butyl-[1-(1-isobutyl-9-methoxymethyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-meth-(E)-ylidene]-amine 
• 81535-34-4 tert-Butyl-[1-(9-methoxymethyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-meth-(E)-ylidene]-amine 

Downstream Products

• 335120-82-6 C₂₄H₂₈N₂O 
• 1227626-13-2 benzyl 1-isobutyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 

Relevant academic research and scientific papers

METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS

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.

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.

Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of the Breast Cancer Resistance Protein (ABCG2)

The breast cancer resistance protein (ABCG2) transports chemotherapeutic drugs out of cells, which makes it a major player in mediating multidrug resistance (MDR) of cancer cells. To overcome this mechanism, inhibitors of ABCG2 can be used. Only a few potent and selective ABCG2 inhibitors have been discovered, i.e., fumitremorgin C (FTC), Ko143, and the alkaloid harmine, which contain a tetrahydro-β-carboline or β-carboline backbone, respectively. However, toxicity and or instability prevent their use in vivo. Therefore, there is a need for further potent inhibitors. We synthesized and pharmacologically investigated 37 tetrahydro-β-carboline derivatives. The inhibitory activity of two compounds (51, 52) is comparable to that of Ko143, and they are selective for ABCG2 over ABCB1. Furthermore, they are able to reverse the ABCG2-mediated resistance toward SN-38 and inhibit the ATPase activity. The cytotoxicity data show that their inhibitory effect is substantially higher than their toxicity.

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.

Tandem intramolecular photocycloaddition-retro-mannich fragmentation as a route to spiro[pyrrolidine-3,3′-oxindoles]. Total synthesis of (±)-coerulescine, (±)-horsfiline, (±)-elacomine, and (±)-6-deoxyelacomine

Figure presented Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-M

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.

Substituted tetrahydro-β-carbolines as potential agents for the treatment of human papillomavirus infection

The identification and optimization of a series of substituted tetrahydro-β-carbolines with potent activity against human papillomavirus is described. Structure-activity studies focused on the substitution pattern and chirality of the β-carboline ring system are discussed. Optimization of these parameters led to compounds with antiviral activities in the low nanomolar range.

Syntheses of tetrahydro-β-carbolines via a tandem hydroformylation- Pictet-Spengler reaction. Scope and limitations

A novel one-pot synthesis of tetrahydro-β-carboline systems via tandem hydroformylation-Pictet-Spengler reaction starting from olefins and aryl ethylamines is described. This tandem procedure allows fast and convenient synthesis of various substituted tetrahydro-β-carbolines. The 2008 Royal Society of Chemistry.

A simple method for the synthesis of 1-substituted β-carboline derivatives from tryptamine and carboxylic acids in polyphosphoric acid

A number of 1-substituted 3,4-dihydro-9H-β-carboline derivatives (4) with high purity and yields have been synthesized by treating of tryptamine (1) with carboxylic acids (2) in polyphosphoric acid. 3,4-Dihydro-9H-β-carbolines (4) were successfully transformed to 1,2,3,4-tetrahydro-9H-β-carbolines (5) and 9H-β-carbolines (6).{A figure is presented}.

THE N-9, C-1 DIANION OF TETRAHYDRO-β-CARBOLINES. REGIOSELECTIVE ALKYLATION LEADING TO INDOLE ALKALOID SYSTEMS

By treatment of β-carboline formamidine (1) with potassium hydride followed by an alkyl lithium reagent, both the pyrrole proton (N-9) and the proton at C-1 are removed.The resulting dianion (3) alkylates cleanly at C-1 and ultimately at N-9 or N-2.