53995-82-7

Usage

Uses

Used in Organic Synthesis:
Ethyl 4,6-dichloroindole-2-carboxylate is used as a building block in organic synthesis for the creation of various bioactive compounds. Its unique structure allows for the development of new chemical entities with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Ethyl 4,6-dichloroindole-2-carboxylate is utilized as an intermediate in the production of pharmaceuticals. Its presence in the synthesis process contributes to the development of new drugs with improved therapeutic properties.
Used in Agrochemical Production:
Ethyl 4,6-dichloroindole-2-carboxylate also serves as an intermediate in the production of agrochemicals. Its use in this industry aids in the development of effective and environmentally friendly solutions for agricultural applications.
Overall, Ethyl 4,6-dichloroindole-2-carboxylate is an important chemical compound for the development of new drugs and agrochemicals, thanks to its versatile structure and potential for synthesis into a wide range of biologically active molecules.

InChI:InChI=1/C11H9Cl2NO2/c1-2-16-11(15)10-5-7-8(13)3-6(12)4-9(7)14-10/h3-5,14H,2H2,1H3

Upstream product

• 4792-68-1 ethyl 2-(2-(2,4-dichlorophenyl)hydrazono)propanoate 
• 554-00-7 2,4-Dichloroaniline 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 63352-99-8 (3,5-dichlorophenyl)hydrazine hydrochloride 
• 39943-56-1 3,5-dichlorophenylhydrazine 
• 626-43-7 3,5-Dichloroaniline 
• 103855-01-2 ethyl 2-[2-(3,5-dichlorophenyl)hydrazinylidene]propanoate 
• 137836-38-5 (E)-ethyl 2-(2-(3,5-dichlorophenyl)hydrazono)propanoate 

Downstream Products

• 153435-96-2 ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate 
• 205646-86-2 ethyl (Z)-4,6-dichloro-3-[2-(3-aminophenyl)2-cyanoethenyl]-1H-indole-2-carboxylate 
• 1099474-22-2 ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate 
• 205646-84-0 ethyl (Z)-4,6-dichloro-3-[2-cyano-2-(3-nitrophenyl)-ethenyl]-1H-indole-2-carboxylate 
• 1473450-60-0 NITD-304 

Relevant academic research and scientific papers

Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent

Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.

Preparation method for 4,6-dichloroindole

The invention discloses a preparation method for 4,6-dichloroindole. The preparation method comprises the following specific steps: in an acidic condition of 3,5-dichloroaniline, carrying out a diazo-reaction on sodium nitrite and then carrying out a condensation reaction with ethyl pyruvate to obtain ethyl-2-(2-(3,5-dichlorophenyl) hydrazono) propionic acid; carrying out ring formation on the ethyl-2-(2-(3,5-dichlorophenyl) hydrazono) propionic acid under the action of lewis acid to obtain 4,6-dichlorindole ethyl formate; hydrolyzing the 4,6-dichlorindole ethyl formate under action of lithium hydroxide to obtain 4,6-dichloroindolecarboxylic acid; and carrying out decarboxylation on the 4,6-dichloroindolecarboxylic acid to obtain 4,6-dichloroindole. The synthetic process of the inventionis more economic, environmentally friendly, efficient and simple.

SPIROCYCLE COMPOUNDS AND METHODS OF MAKING AND USING SAME

Provided herein are compounds and compositions useful as modulators of MAGL. Furthermore, the subject compounds and compositions are useful for the treatment of pain.

Remarkable Enhancement in Boron Uptake Within Glioblastoma Cells With Carboranyl–Indole Carboxamides

Novel boron-rich, carboranyl–indole carboxamide ligands were prepared and found to effectively target the 18 kDa translocator protein (TSPO), an upregulated mitochondrial membrane-bound protein which has been observed in variety of tumor cell lines and its expression appears to be proportional to the degree of tumorigenicity, emphasizing a key role in cancer cell proliferation. Both boronated compounds displayed remarkably high affinities for the TSPO. In addition, the in vitro uptake of these compounds into T98G human glioma cells was found to be 25- to 100-fold greater than that of clinical boron neutron capture therapy (BNCT) agents.

Environmentally friendly method for preparing 4,6-dihalogen-substituted indole-2-ethyl formate

The invention discloses a preparation method of 4,6-dihalogen-substituted indole-2-ethyl formate, the preparation method is characterized in that ethyl pyruvate-3,5-dihalophenylhydrazone is used as araw material for cyclizing in a polyphosphoric acid and toluene mixed solvent system to form 3,5-dihalogen-substituted indole-2-ethyl formate, and the target compound is isolated by liquid-liquid extraction of a reaction mixture. The method is simple in operation, free of waste water discharge, green, environmentally friendly and suitable for industrial production.

Preparation method and application of indolo pyridone compounds with antitumor activity

The invention discloses a preparation method and an application of indolo pyridone compounds with antitumor activity, and belongs to the technical field of medicine synthesis. The technical scheme ischaracterized in that the structural formula of the indo

Novel indolopyridone drug molecule as well as preparation method and application thereof

The invention discloses a novel indolopyridone drug molecule as well as a preparation method and application thereof and belongs to the technical field of pharmaceutical synthesis. According to the technical scheme provided by the invention, the novel ind

From Cells to Mice to Target: Characterization of NEU-1053 (SB-443342) and Its Analogues for Treatment of Human African Trypanosomiasis

Human African trypanosomiasis is a neglected tropical disease that is lethal if left untreated. Existing therapeutics have limited efficacy and severe associated toxicities. 2-(2-(((3-((1H-Benzo[d]imidazol-2-yl)amino)propyl)amino)methyl)-4,6-dichloro-1H-indol-1-yl)ethan-1-ol (NEU-1053) has recently been identified from a high-throughput screen of >42,000 compounds as a highly potent and fast-acting trypanocidal agent capable of curing a bloodstream infection of Trypanosoma brucei in mice. We have designed a library of analogues to probe the structure-activity relationship and improve the predicted central nervous system (CNS) exposure of NEU-1053. We report the activity of these inhibitors of T. brucei, the efficacy of NEU-1053 in a murine CNS model of infection, and identification of the target of NEU-1053 via X-ray crystallography.

Discovery of 3-Substituted 1H-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT1 Selective Antagonists

The indole derivative, 3-((E)-3-((3-((E)-2-(7-chloroquinolin-2yl)vinyl)phenyl)amino)-3-oxoprop-1-en-1-yl)-7-methoxy-1H-indole-2-carboxylic acid (17k), was identified as a novel and highly potent and selective CysLT1 antagonist with IC50 values of 0.0059 ± 0.0011 and 15 ± 4 μM for CysLT1 and CysLT2, respectively.

Development of [3H]2-carboxy-4,6-dichloro-1 H -indole-3-propionic acid ([3H]PSB-12150): A useful tool for studying GPR17

The recently described synthetic GPR17 agonist 2-carboxy-4,6-dichloro-1H- indole-3-propionic acid (1) was prepared in tritium-labeled form by catalytic hydrogenation of the corresponding propenoic acid derivative 8 with tritium gas. The radioligand [3H]PSB-12150 (9) was obtained with a specific activity of 17 Ci/mmol (629 GBq/mmol). It showed specific and saturable binding to a single binding site in membrane preparations from Chinese hamster ovary cells recombinantly expressing the human GPR17. A competition assay procedure was established, which allows the determination of ligand binding affinities.