448906-42-1

Basic information

• Product Name: ITE
• Synonyms: ITE;2-(1H-INDOL-3-YLCARBONYL)-4-THIAZOLECARBOXYLIC ACID METHYL ESTER;2-(1'H-INDOLE-3'-CARBONYL)-THIAZOLE-4-CARBOXYLIC ACID;2-(1'H-indole-37-carbonyl)-thiasole-4-carboxylic acid methyl ester;Methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate
• CAS NO: 448906-42-1
• Molecular Formula: C₁₄H₁₀N₂O₃S
• Molecular Weight: 286.31
• Mol File: 448906-42-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 520.4 °C at 760 mmHg
• Flash Point: 268.5 °C
• Appearance: /solid
• Density: 1.427 g/cm³
• Vapor Pressure: 6.24E-11mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• Solubility: DMSO: 30 mg/mL, soluble
• PKA: 14.38±0.30(Predicted)
• CAS DataBase Reference: ITE(CAS DataBase Reference)
• NIST Chemistry Reference: ITE(448906-42-1)
• EPA Substance Registry System: ITE(448906-42-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 448906-42-1(Hazardous Substances Data)

Usage

Description

Methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate is a chemical compound that belongs to the class of thiazole carboxylates. It is characterized by its unique molecular structure, which consists of a thiazole ring fused to an indole ring, with a carboxylate group attached to the thiazole ring and a methyl group attached to the carboxylate. methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate is known for its potential applications in various fields due to its chemical properties and interactions with other molecules.

Uses

Used in Pharmaceutical Industry:
Methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate is used as a pharmaceutical candidate for the development of new drugs. Its unique molecular structure allows it to interact with various biological targets, making it a promising compound for the treatment of various diseases.
Used in Chemical Research:
In the field of chemical research, methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate serves as a valuable compound for studying the properties and reactivity of thiazole carboxylates. Its synthesis and modification can provide insights into the development of new chemical reactions and the design of novel molecules with specific functions.
Used in Agricultural Industry:
Methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate can be used as a component in the development of new agrochemicals, such as pesticides or herbicides. Its ability to interact with biological targets can be exploited to create compounds that can effectively control pests and weeds in agriculture.
Used in Environmental Applications:
methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate can also be utilized in environmental applications, such as the development of new materials for pollution control or the remediation of contaminated sites. Its chemical properties may allow it to be used in the design of novel adsorbents or catalysts for the removal of harmful substances from the environment.
Used in Endogenous AHR Ligand Research:
Methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate is used as an endogenous AHR ligand for the induction of FoxP3+ Treg cells, which play a crucial role in suppressing experimental autoimmune encephalomyelitis. This application promotes the induction of active immunology tolerance and helps identify nontoxic endogenous AHR ligands for further research and potential therapeutic applications.

Biological Activity

Endogenous agonist for the transcription factor aryl hydrocarbon receptor (AHR); K i = 3 nM for binding to murine AHR. Transactivates DRE-containing reporter gene constructs in Hepa1c1c7 cells ~ 5-fold more potently than β -naphthoflavone. Active in vivo .

InChI:InChI=1/C14H10N2O3S/c1-19-14(18)11-7-20-13(16-11)12(17)9-6-15-10-5-3-2-4-8(9)10/h2-7,15H,1H3

Upstream product

• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 585533-85-3 (2R)-2-[2'-(1H-indol-3-yl)-2'-oxo-acetyloamino]-3-mercaptopropionic acid methyl ester 
• 7425-63-0 methyl 3-bromo-2-oxopropanoate 
• 120-72-9 indole 
• 5548-10-7 indole-3-glyoxylamide 
• 19194-62-8 1H-indol-3-yl(oxo)acetonitrile 
• 771-50-6 1H-indole-3-carboxylic acid 
• 67-56-1 methanol 
• 214759-95-2 N-methoxy-N-methyl-1H-indole-3-carboxamide 
• 675606-20-9 1-(tert-butoxycarbonyl)-1H-indole-3-carboxylic acid 
• 5714-80-7 cysteine methyl ester hydrochloride 

Relevant articles and documents

2-(1H-INDOLE-3-CARBONYL)-THIAZOLE-4-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

2-(1H-lndole-3-carbonyl)-thiazole-4-carboxamide derivatives and the corresponding imidazole, oxazole and thiophene derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders. The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 27 to 32 and 59 to 219; examples 1 to 8; compounds 1-1 to 1-97; tables 1-a, 2 and 3).

PROCESSES FOR THE PREPARATION OF ARYL HYDROCARBON RECEPTOR LIGANDS

The present disclosure relates to the preparation of methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate (ITE) and related compounds with high yield, purity, and scalability. The processes apply the use of a Weinreb amide intermediate as a scaffold for the preparation of ITE and structural analogs.

A concise synthesis of an AHR endogenous ligand with the indolecarbonylthiazole skeleton

Short synthesis of an endogenous ligand for the arylhydrocarbon receptor (AHR), 2-(1′H-indole-3′-carbonyl)thiazole-4-carboxylic acid methyl ester (7), has been described. N-Acylation of the L-cysteine methyl ester (4) with indoleglyoxylyl chloride (1) pro