3389-21-7

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(2-Bromoethyl)indole is used as a key intermediate in the synthesis of β-carboline derivatives, which are known for their diverse biological activities, including potential applications in the treatment of neurological disorders and as anticancer agents.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(2-Bromoethyl)indole is used as a building block for the preparation of 6,7-dihydro-12H-indolo[2,3-a]pyridocolinium bromide. 3-(2-BROMOETHYL)INDOLE can be further utilized in the development of novel organic materials and pharmaceuticals.
Used in Crown Ether Synthesis:
3-(2-Bromoethyl)indole is employed as a starting material for the synthesis of N-(2-(3-indolyl)ethyl)aza-crown ethers, such as N-(2-(3-Indolyl)ethyl)aza-12-crown-4, N-(2-(3-Indolyl)ethyl)aza-15-crown-5, and N-(2-(3-Indolyl)ethyl)aza-18-crown-6. These crown ethers have potential applications in supramolecular chemistry, as they can form complexes with various metal ions and organic substrates, leading to their use in sensors, catalysts, and drug delivery systems.
Overall, 3-(2-Bromoethyl)indole is a versatile chemical intermediate with applications in various industries, including pharmaceuticals, organic synthesis, and supramolecular chemistry. Its unique structure and reactivity make it a valuable component in the development of new compounds and materials with potential applications in medicine, materials science, and beyond.

InChI:InChI=1/C10H10BrN/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2

Upstream product

• 526-55-6 2-(3-indole)-ethanol 
• 121459-15-2 2-(1H-indol-1-yl)ethanol 
• 120-72-9 indole 
• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 100-63-0 phenylhydrazine 

Downstream Products

• 4695-86-7 3-methoxycarbonyl-1-[2-(3-indolyl)ethyl]pyridinium bromide 
• 61-52-9 Dipropyltryptamine 
• 15741-77-2 dibutyl-(2-indol-3-yl-ethyl)-amine 
• 61-50-7 N,N-dimethyltryptamine 
• 14121-10-9 N-(2-(1H-indol-3-yl)ethyl)propan-2-amine 
• 61-51-8 N,N-diethyltryptamine 
• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 60676-77-9 N,N-diallyltryptamine 
• 351421-21-1 diethyl 2-(2-(1H-indol-3-yl)ethyl)-2-acetamidomalonate 
• 61-54-1 tryptamine 
• 168104-03-8 (S)-N-(2-(1H-indol-3-yl)ethyl)-1-phenylethanamine 
• 568589-89-9 N,N'-di(benzyloxycarbonyl)-3-[2-(indol-3-yl)ethyl]-3-aza-1,6-hexanediamine 
• 915951-04-1 C₃₄H₃₆N₂O₄ 
• 6245-92-7 2-amino-4-indol-3-yl-butyric acid 

Relevant academic research and scientific papers

Synthesis and Studies of Potential Inhibitors of CD73 Based on a Triazole Scaffold

The ecto-5′-nucleotidase CD73 is involved in the production of immunosuppressive adenosine in the tumoral microenvironment and recently became a validated target in immuno-oncology. To avoid formation of CD73-produced adenosine, several series of potential inhibitors of the target enzyme based on a triazole scaffold were synthetized and evaluated on recombinant purified hCD73 and in cell-based assays.

A convenient synthesis of indole and 1,4-dihydropyridine hybrid macromolecules by dimerization of [2-(1h-indol-3-yl)ethyl]pyridinium salts

The design and synthesis of a novel type of macrocyclic compounds containing indole and 1,4-dihydropyridine heterocyclic subunits is presented. The key reaction involved in the synthesis was a base-mediated dimerization of [2-(1H-indol-3-yl)ethyl]pyridinium salts. The structure of the macrocycles was unambiguously confirmed by NMR and HRMS spectroscopic and X-ray single crystal diffraction.

8-aminoquinoline-melatonin complex and pharmaceutical composition thereof

The invention relates to synthesized 8-aminoquinoline-melatonin complex, in particular to an 8-aminoquinoline-melatonin complex and a pharmaceutical composition thereof. The 8-aminoquinoline-melatonin complex is of a structure as shown in the structural formula (I); on one hand, the compounds can selectively chelate copper ions; on the other hand, the compounds play a role in well protecting nerves and nerve cells to improve AD (Alzheimer's disease) symptoms. The invention further relates to a pharmaceutical composition or nerve cell protective agent comprising the complex or pharmaceutically acceptable salt thereof. The invention further relates to pharmaceutical application of the complex.

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.

Inhibition of Escherichia coli tryptophan indole-lyase by tryptophan homologues

We have designed, synthesized and evaluated homotryptophan analogues as possible mechanism-based inhibitors for Escherichia coli tryptophan indole-lyase (tryptophanase, TIL, E.C. 4.1.99.1). As a quinonoid structure is an intermediate in the reaction mechanism of TIL, we anticipated that homologation of the physiological substrate, l-Trp would provide analogues resembling the transition state for β-elimination, and potentially inhibit TIL. Our results demonstrate that l-homotryptophan (1a) is a moderate competitive inhibitor of TIL, with Ki = 67 μM, whereas l-bishomotryptophan (1b) displays more potent inhibition, with Ki = 4.7 μM. Pre-steady-state kinetics indicated the formation of an external aldimine and quinonoid with 1a, but only the formation of an external aldimine for 1b, suggesting differences in the inhibition mechanism. These results demonstrate that formation of a quinonoid complex is not required for strong inhibition. In addition, the Trp analogues were evaluated as inhibitors of Salmonella typhimurium Trp synthase. Our results indicate that compound 1b is at least 25-fold more selective toward TIL than Trp synthase. We report that compound 1b is comparable to the most potent inhibitor previously reported, while displaying high selectivity for TIL. Thus, 1b is a potential lead for the development of novel antibacterials.

Synthesis and evaluation of novel 2,3-dihydrobenzo[b][1,4]dioxin- and indolealkylamine derivatives as potential antidepressants

A series of 2,3-dihydrobenzo[b][1,4]dioxin- and indolealkylamine derivatives were synthesized and the target compounds were evaluated for their binding affinities at the 5-HT1A receptor and serotonin transporter. Antidepressant-like activities of the compounds were screened using the tail suspension and forced swim tests in mice. Preliminary results indicated that the target compounds exhibited high binding affinities at the 5-HT1A receptor and serotonin transporter, and produced marked antidepressant-like effects. The best example from this study, compound 5, exhibited high binding affinities for the 5-HT1A receptor (Ki = 96 nM) and serotonin transporter (Ki = 9.8 nM). The intrinsic activity of compound 5 showed agonistic property to the 5-HT1A receptor and inhibition of the 5-HT transporter. Furthermore, compound 5 exhibited greater antidepressant efficacy than fluoxetine and showed acceptable pharmacokinetic properties. A series of 3-(2-(4-((2,3-dihydrobenzo[b][1,4]dioxin-3-yl)methyl) piperazin-1-yl)ethyl-1H-indole derivatives were synthesized and the target compounds were evaluated for their antidepressant activities in vitro and in vivo. The compounds described were also evaluated for dual 5-HTT and 5-HT 1A receptor activities.

The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow

The application of a monolithic form of triphenylphosphine to the Ramirez gem-dibromoolefination reaction using flow chemistry techniques is reported. A variety of gem-dibromides were synthesised in high purity and excellent yield following only removal of solvent and no further off-line purification. It is also possible to perform the Appel reaction using the same monolith and the relationship between the mechanisms of the two reactions is discussed.

Biomimetic total syntheses of borreverine and flinderole alkaloids

Dimeric indole alkaloids represent a structurally unique class of natural products having interesting biological activities. Recently, we reported the first total synthesis of flinderoles B and C, structurally unique and potent antimalarial natural products. Central to the design of the approach and by virtue of a one-pot, acid-catalyzed dimerization reaction, the route also provided total synthesis of the borreverine class of natural products. This full account details the progress of efforts that culminated in the protecting-group-free, six-step total synthesis of all of the flindersia alkaloids: dimethylisoborreverine, isoborreverine, flinderoles A-C, and their analogues. A biomimetic approach featuring a scalable and catalytic formal [3 + 2] cycloaddition and Diels-Alder reaction is outlined in detail. On the basis of the experimental observations, a detailed mechanism has been proposed for the dimerization of tertiary alcohol 28.

Manganese-catalyzed aerobic dehydrogenative cyclization toward ring-fused indole skeletons

We describe the first example of manganese(iii)-catalyzed aerobic dehydrogenative cyclization producing ring-fused indole skeletons. This catalytic system converts from two C-H bonds of indole and malonate to a C-C bond and produces water as the sole side product. This operationally easy method was extended to an intermolecular cross-dehydrogenative coupling of indole and α-substituted malonate with complete C2-selectivity.

NOVEL BENZAMIDE DERIVATIVES

The present invention provides a novel benzamide derivative or a pharmaceutically acceptable salt thereof, a method for preparing the same, and a 5-HT4 receptor agonist containing the same as an active ingredient. Benzamide derivatives of the present invention have a superior affinity for 5-HT4 receptors, a capability to reduce a gastric emptying time and a low toxicity, and consequently are therapeutically effective for the treatment of a variety of diseases associated with 5-HT4 receptors.