117637-79-3

Basic information

• Product Name: Ethyl 3-iodo-1H-indole-2-carboxylate
• Synonyms: Ethyl 3-iodo-1H-indole-2-carboxylate;ethyl 3-iodo-1H-indol-2-carboxylate
• CAS NO: 117637-79-3
• Molecular Formula: C₁₁H₁₀INO₂
• Molecular Weight: 315
• Mol File: 117637-79-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl 3-iodo-1H-indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-iodo-1H-indole-2-carboxylate(117637-79-3)
• EPA Substance Registry System: Ethyl 3-iodo-1H-indole-2-carboxylate(117637-79-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 117637-79-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl 3-iodo-1H-indole-2-carboxylate is used as a building block for the synthesis of various organic compounds due to its reactivity and structural versatility.
Used in Medicinal Chemistry:
Ethyl 3-iodo-1H-indole-2-carboxylate is used as a starting material for the development of pharmaceutical products, as its unique structure and properties can be exploited to create new drug candidates.
Used in Drug Discovery:
Ethyl 3-iodo-1H-indole-2-carboxylate is used as a research reagent in the field of drug discovery, where its potential applications in the development of new therapeutic agents are explored.
Used in Chemical Biology:
Ethyl 3-iodo-1H-indole-2-carboxylate is used in chemical biology to study the interactions between small molecules and biological targets, contributing to the understanding of biological processes and the development of new therapeutic strategies.
Used in Agrochemicals:
Ethyl 3-iodo-1H-indole-2-carboxylate is used as a building block for the preparation of agrochemical products, such as pesticides and herbicides, due to its reactivity and potential applications in this field.

Upstream product

• 3770-50-1 2-carbethoxyindole 
• 1477-50-5 Indole-2-carboxylic acid 

Downstream Products

• 1334544-35-2 9-benzyl-3-phenylindolo[2,3-c]pyrane-1(9H)-one 
• 1334544-42-1 9-benzyl-3-o-tolylindolo[2,3-c]pyrane-1(9H)-one 
• 1334544-36-3 9-benzyl-3-p-tolylindolo[2,3-c]pyrane-1(9H)-one 
• 1334544-43-2 9-benzyl-3-(pyridin-2-yl)indolo[2,3-c]pyrane-1(9H)-one 
• 1334544-37-4 9-benzyl-3-(thiophen-3-yl)indolo[2,3-c]pyrane-1(9H)-one 
• 1334544-38-5 9-benzyl-3-butylindolo[2,3-c]pyrane-1(9H)-one 
• 1334544-44-3 (E)-9-benzyl-3-[2-(2,6,6-trimethylcyclohex-2-enyl)vinyl]indolo[2,3-c]pyrane-1(9H)-one 
• 1334544-39-6 (E)-9-benzyl-3-[2-(2,6,6-trimethylcyclohex-1-enyl)vinyl]indolo[2,3-c]pyrane-1(9H)-one 
• 1334544-40-9 diethyl-2-[(9-benzyl-1,9-dihydroindolo[2,3-c]pyrane-3-yl)methyl]-2-(prop-2-ynyl)malonate 
• 1263209-59-1 1-benzyl-3-iodo-indole-2(1H)-carboxylic acid 

Relevant articles and documents

Axially Chiral Aryl-Alkene-Indole Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction

A new class of axially chiral aryl-alkene-indole frameworks have been designed, and the first catalytic asymmetric construction of such scaffolds has been established by the strategy of organocatalytic (Z/E)-selective and enantioselective (4+3) cyclization of 3-alkynyl-2-indolylmethanols with 2-naphthols or phenols (all >95 : 5 E/Z, up to 98% yield, 97% ee). This reaction also represents the first catalytic asymmetric construction of axially chiral alkene-heteroaryl scaffolds, which will add a new member to the atropisomeric family. This approach has not only confronted the great challenges in constructing axially chiral alkene-heteroaryl scaffolds but also provided a powerful strategy for the enantioselective construction of axially chiral aryl-alkene-indole frameworks.

Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM

In this study, we screen three heterocyclic structures as potential inhibitors of UDP-galactopyranose mutase (UGM), an enzyme involved in the biosynthesis of the cell wall of Mycobacterium tuberculosis. In order to understand the binding mode, docking simulations are performed on the best inhibitors. Their activity on Mycobacterium tuberculosis is also evaluated. This study made it possible to highlight an “oxazepino-indole” structure as a new inhibitor of UGM and of M. tuberculosis growth in vitro.

Synthesis and Reactivity of Oxazinoindolones via Regioselective 6-exo-dig Iodolactonization

An efficient protocol for the facile construction of 3,4-dihydro-10-iodo-3-iodomethylene-[1,4]-oxazino[4,3-a]indol-1-ones has been developed by using a regio- and stereoselective iodolactonization reaction. Subsequent palladium cross-coupling reactions of 3,4-dihydro-10-iodo-3-iodomethylene-[1,4]-oxazino[4,3-a]indol-1-ones readily afforded functionalized oxazinoindolones.

Neuroprotective Effect of IND1316, an Indole-Based AMPK Activator, in Animal Models of Huntington Disease

Aggregation of mutant huntingtin, because of an expanded polyglutamine track, underlies the cause of neurodegeneration in Huntington disease (HD). However, it remains unclear how some alterations at the cellular level lead to specific structural changes in HD brains. In this context, the neuroprotective effect of the activation of AMP-activated protein kinase (AMPK) appears to be a determinant factor in several neurodegenerative diseases, including HD. In the present work, we describe a series of indole-derived compounds able to activate AMPK at the cellular level. By using animal models of HD (both worms and mice), we demonstrate the in vivo efficacy of one of these compounds (IND1316), confirming that it can reduce the neuropathological symptoms of this disease. Taken together, in vivo results and in silico studies of druggability, allow us to suggest that IND1316 could be considered as a promising new lead compound for the treatment of HD and other central nervous system diseases in which the activation of AMPK results in neuroprotection.

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

INDOLE DERIVATIVES FOR THE PREVENTION AND/OR TREATMENT OF DIABETES AND ASSOCIATED METABOLIC DISORDERS

The invention relates to substituted heterocyclic indole derivatives of Formula (I), which act as activators of the AMP-activated protein kinase (AMPK) and to the use of them for the treatment and prevention of diseases or disorders regulated by AMPK. As

Palladium nanoparticles on graphite oxide: A recyclable catalyst for the synthesis of biaryl cores

The synthesis of life saving drug molecules in a cost-effective and environmentally benign pathway is of paramount significance. We present an environment friendly protocol to prepare core moieties of top selling drug molecules such as boscalid and telmisartan using Suzuki-Miyaura coupling conditions. In contrast to the traditional synthesis of these pharmaceutically important molecules, we have accomplished a graphite oxide (GO) supported palladium nanoparticles (PdNPs) based catalyst which quantitatively produced these core biaryl moieties of top selling drug molecules in a recyclable way. The catalytic activity remained unchanged even after 16 successive catalytic cycles without incorporating any palladium metal impurity in the pharmaceutically significant organic products. A detailed study including IR spectroscopy, solid state NMR spectroscopy, X-ray photoelectron spectroscopy, and DFT calculation was employed to understand the role of solid support on the nondecaying recycling ability of the catalyst during the Suzuki-Miyaura coupling reaction. The study indicates a strong chemical interaction of the different functionalities present in the GO, with the palladium centers which is primarily responsible for such sustained catalytic activity during the consecutive Suzuki-Miyaura coupling cycles.