59444-69-8

Basic information

• Product Name: eudistomin N
• Synonyms: eudistomin N;6-Bromo-9H-pyrido[3,4-b]indole;6-Bromonorharman;Eudistomine N
• CAS NO: 59444-69-8
• Molecular Formula: C₁₁H₇BrN₂
• Molecular Weight: 247.09068
• Mol File: 59444-69-8.mol

Chemical Properties

• Boiling Point: 443.6°C at 760 mmHg
• Flash Point: 222.1°C
• Appearance: /
• Density: 1.699g/cm³
• Vapor Pressure: 1.2E-07mmHg at 25°C
• Refractive Index: 1.799
• CAS DataBase Reference: eudistomin N(CAS DataBase Reference)
• NIST Chemistry Reference: eudistomin N(59444-69-8)
• EPA Substance Registry System: eudistomin N(59444-69-8)

Safety Data

• Hazardous Substances Data: 59444-69-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H7BrN2/c12-7-1-2-10-9(5-7)8-3-4-13-6-11(8)14-10/h1-6,14H

Upstream product

• 244-63-3 betacarboline 
• 6250-88-0 4,9-Dihydropyrano<3,4-b>indol-1(3H)-on 
• 110977-90-7 6-Brom-4,9-dihydropyrano<3,4-b>indol-1(3H)-on 
• 42438-90-4 3-carboxy-1,2,3,4-tetrahydro-2-carboline 
• 73-22-3 L-Tryptophan 
• 162272-84-6 6-Brom-2-(4-chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-on 
• 162272-89-1 2-(4-Chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol 
• 162272-83-5 2-(4-Chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-on 
• 162272-90-4 6-Brom-2-(4-chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol 

Downstream Products

• 1221437-41-7 6-bromo-2-(3-phenyl-propyl)-9H-beta-carbolin-2-ium bromide 
• 1221437-37-1 2-benzyl-6-bromo-9H-beta-carbolin-2-ium bromide 
• 1221437-39-3 6-bromo-2-(3-fluoro-benzyl)-9H-beta-carbolin-2-ium bromide 
• 1221437-38-2 6-bromo-2-(4-fluoro-benzyl)-9H-beta-carbolin-2-ium bromide 
• 1221437-40-6 6-bromo-2-(4-nitro-benzyl)-9H-beta-carbolin-2-ium bromide 

Relevant articles and documents

A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air

A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.

METHODS AND COMPOUNDS FOR RESTORING MUTANT p53 FUNCTION

Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The present disclosure describes compounds and methods that restore DNA binding affinity of p53 mutants. The compounds of the present disclosure can bind to mutant p53 and restore the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation.

Iodine-catalyzed one-pot decarboxylative aromatization of tetrahydro-β-carbolines

A synthetic strategy was developed for the preparation of β-carbolines by one-pot decarboxylation and aromatization of tetrahydro-β-carboline-3-carboxylic acids by employing 10?mol% of iodine in presence of oxidant aqueous H2O2. The method was also successfully extended for the aromatization of tetrahydro-β-carboline-3-methyl esters. The utility of the method was demonstrated in the synthesis of β-carboline alkaloids norharmane, harmane and eudistomin N.

Phosphorescent host compound and organic electroluminescent device thereof

The invention provides a phosphorescent host compound represented by a structural formula (I). The compound has better heat stability and high light-emitting efficiency and light-emitting purity, can be used for manufacturing organic electroluminescent devices and is applied to the fields of organic solar cells, organic thin-film transistors or organic photoreceptors. The invention further provides an organic electroluminescent device. The organic electroluminescent device comprises an anode, a cathode and organic layers, wherein the organic layers include one or more of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electronic injection layer and an electronic transport layer, and at least one of the organic layers contains the compound represented by the structural formula (I) (shown in the description).

An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.

Novel IKK inhibitors: β-carbolines

Inhibitors of IκB kinase (IKK) have long been sought as specific regulators of NF-κB. A screening effort of the endogenous IKK complex allowed us to identify 5-bromo-6-methoxy-β-carboline as a nonspecific IKK inhibitor. Optimization of this β-carboline natural product derivative resulted in a novel class of selective IKK inhibitors with IC50s in the nanomolar range. In addition, we show that one of these β-carboline analogues inhibits the phosphorylation of IκBα and subsequent activation of NF-κB in whole cells, as well as blocking TNF-α release in LPS-challenged mice.

Substituted beta-carbolines

Compounds of the formula I are suitable for the production of pharmaceuticals for the prophylaxis and therapy of disorders in whose course an increased activity of IκB kinase is involved.

Synthesis and isolation of bromo-β-carbolines obtained by bromination of β-carboline alkaloids

β-Carbolines (1-5) undergo electrophilic aromatic substitution with N-bromosuccinimide under different experimental conditions. Although 6-bromo-nor-harmane (1a) obtained by bromination of nor-harmane (1) was isolated and fully characterized sometime ago,

Indoles, XII: β-Carbolines from lactones - Synthesis of ligands of the norharmane receptor

Starting from α-ethoxalyl-δ-valerolactone (1) 6-substituted β-carbolines were synthesized in 5 steps to enable investigations at the norharmane binding sites in rat liver and in pig brain. The Pd-catalyzed aromatization of N-benzyl-tetrahydro-β-carbolines with debenzylation was optimized with 5a → 6a and then used for the preparation of other derivatives. Additional hydrogenolyses occur with 5d,h. Bromination of 1a gives 6d which can be transferred to the radioligand 3H-norharmane.

A new method for bromination of carbazoles, β-carbolines and iminodibenzyls by use of N-bromosuccinimide and silica gel

Carbazole, N-ethylcarbazole, iminodibenzyl (10,11-dihydro-5H-dibenz[b,f]azepine), N-ethyliminodibenzyl and imipramine are readily mono-, di- or polybrominated in high yields at ambient temperature in dichloromethane by use of the appropriate quantity of N-bromosuccinimide in the presence of silica gel. By contrast, the brominations of the β-carbolines, harmane and norharman, are less selective and give mixtures of products, some of which have unusual substitution patterns.