921194-97-0

Basic information

• Product Name: 1H-INDOLE-3-CARBOXYLIC ACID,6-CHLORO-,METHYL ESTER
• Synonyms: 1H-INDOLE-3-CARBOXYLIC ACID,6-CHLORO-,METHYL ESTER;methyl 6-chloro-1H-indole-3-carboxylate;6-Chloro-1H-indole-3-carboxylic acid methyl ester;6-Chloro-1H-indole-3-Carbocylic acid methyl ester
• CAS NO: 921194-97-0
• Molecular Formula: C10H8ClNO2
• Molecular Weight: 209.63
• Mol File: 921194-97-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1H-INDOLE-3-CARBOXYLIC ACID,6-CHLORO-,METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE-3-CARBOXYLIC ACID,6-CHLORO-,METHYL ESTER(921194-97-0)
• EPA Substance Registry System: 1H-INDOLE-3-CARBOXYLIC ACID,6-CHLORO-,METHYL ESTER(921194-97-0)

Safety Data

• Hazardous Substances Data: 921194-97-0(Hazardous Substances Data)

Usage

General Description

1H-Indole-3-carboxylic Acid, 6-chloro-, Methyl Ester is a chemical compound with the molecular formula C11H9ClNO2. Structurally related to indole, this substance is comprised of a methyl group, a carboxylic acid group, and a chlorine atom bound to an indole, which is an aromatic heterocyclic organic compound. It predominantly exists as a white to beige crystalline solid. This chemical is used primarily in research and is often utilized in the synthesis of various other chemicals or pharmaceuticals. Safety measures should be exercised during its handling due to potential hazardous properties.

Upstream product

• 121-73-3 3-Nitrochlorobenzene 
• 10468-17-4 N-(3-chlorophenyl)hydroxylamine 
• 922-67-8 propynoic acid methyl ester 
• 67-56-1 methanol 
• 766557-02-2 6-chloro-1H-indole-3-carboxylic acid 

Relevant articles and documents

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

De Novo Synthesis of Benzannelated Heterocycles

Benzannelated heterocycles such as indoles and indazoles are prominent structural motifs found in natural products, pharmaceuticals and agrochemicals. For their synthesis, chemists traditionally either functionalize commercially available heterocycles or resort to transformations that make use of benzene-derived building blocks. Here, we report a powerful cascade reaction that enables the de novo construction of variously substituted indoles, indazoles, benzofurans and benzothiophenes from readily available bicyclo[3.1.0]hexan-2-ones. The transformation can be conducted under mild, non-anhydrous conditions. For the synthesis of indoles, mechanistic studies revealed that the electrocyclic ring-opening of the bicyclic ring-system and aromatization precedes the 3,3-sigmatropic rearrangement.