99545-51-4

Upstream product

• 343-94-2 tryptamine hydochloride 
• 122-78-1 phenylacetaldehyde 
• 61-54-1 tryptamine 
• 73955-63-2 2-benzyl-3,4,4-trimethyl-1-(toluene-4-sulfonyl)-imidazolidine 
• 36873-30-0 2-benzyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine 
• 766-04-1 benzyllithium 
• 116965-61-8 2,9-bis-(trimethylsilyl)-3,4-dihydropyrido<3,4-b>indolium trifluoromethane sulphonate 
• 959859-89-3 N-(triphenylmethanesulfenyl)tryptamine 
• 10022-80-7 1-benzyl-4,9-dihydro-3H-pyrido-[3,4-b]indole 
• 103-82-2 phenylacetic acid 
• 1589-82-8 phenylmagnesium bromide 
• 4894-26-2 3,4-dihydro-β-carboline 
• 38879-46-8 (Z)-4-benzylidene-2-methyl-5(4H)-oxazolone 
• 100-52-7 benzaldehyde 

Downstream Products

• 16765-80-3 1-benzyl-β-carboline 
• 913289-12-0 1-benzyl-2-ethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 

Relevant academic research and scientific papers

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.

Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities

A series of 1-indolyl substituted β-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation - oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked β-carboline analogues for structure-activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A2 (IC50 171 and 131 μM, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 μM). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of β-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 μM). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines.

1-Benzyl-1,2,3,4-Tetrahydro-β-Carboline as Channel Blocker of N-Methyl-d-Aspartate Receptors

N-methyl-d-aspartate (NMDA) receptors belong to the family of ligand-gated ion channels and are important for synaptic plasticity and memory function. The NMDA receptor consists of a voltage-dependent channel permeable to Ca2+ and Na+/sup

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.

Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus

β-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compoun

Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions

(Chemical Equation Presented) From cations to chiral products: β-Carbo-lines can be synthesized with good enantioselectivity by the title reaction catalyzed by a chiral binol-derived Bronsted acid (see scheme, BHT = 3,5-di(tert-butyl)-4-hydroxytoluene). T

Reaction of 1-substituted tetrahydro-β-carbolines with activated alkynes - A new original approach to the synthesis of tetrahydroazocino[5,4-b] indoles

The transformations of 1-substituted tetrahydro-β-carbolines by the action of activated alkynes were studied. The action of dimethyl acetylenedicarboxylate in methanol gives products of the opening of the tetrahydropyridine fragment, namely, 2-methoxyalkylindoles. The action of ethyl propiolate in ethanol and of tosylacetylene in methanol gives mixtures of azocino[5,4-b]indoles and 2-alkoxyindoles. The action of ethyl propiolate in acetonitrile gives azocinoindoles.

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}.

Potent, selective tetrahydro-β-carboline antagonists of the serotonin 2B (5HT(2B)) contractile receptor in the rat stomach fundus

A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (- log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-β- carboline antagonists are able to discriminate among the 5HT2 family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-β- carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

Alkylation of 3,4-dihydro-β-carboline

A new general procedure for the alkylation of the C = N double bond of 3,4-dihydro-β-carboline has been developed with amphiphilic reaction systems such as BF3 · OEt2/RLi, RMgX, R2CuLi or trimethylsilyl trifluoromethanesulfonate/RLi, RMgX to give the corresponding 1-substituted-1,2,3,4-tetrahydro-β-carbolines.