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

Uses

ITE is an endogenous AHR ligand that parenterally or orally induces FoxP3+ Treg that suppress exprimental autoimmune encephalomyelitis. ITE promotes the induction of active immunology tolerance and identifies nontoxic endogenous AHR ligands.

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

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

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).

Compound containing 2,4 - thiazole ring and preparation method and application thereof

The invention provides a compound containing 2,4 - thiazole rings and a preparation method and application thereof, wherein the compound is shown in a formula X. A Is pyrazolopyrimidine or indole. Z Is carbonless. X Is O or S. Y Is - O - or - NH . R1 Hydrogen or C1 -6 Alkyl. R2 Be selected from C1 - C3 Alkyl. C5 - C15 Alkenyl, alkynyl, 5 - RMB 10 heterocyclic radicals, C6 - C12 Aryl, 5 -12 membered heteroaryl, sterol and 5-10 元 cycloalkyl. Y And R2 Connection, or Y and R2 Looping. R3 From hydrogen. Halogen, amino, hydroxyl, acetyl, 3 - RMB 10 heterocyclic group, C6 - C12 Aryl, 5 -12-membered heteroaryl, 3 -10-membered cycloalkyl, ester, carboxy, trihalomethyl and adamantyl. R2 Or R3 It is unsubstituted or is selected from C. 1 - C6 Alkyl. A hydroxy group, a halogen group, a trihalomethyl group, a carboxyl group, and a phenyl group. R2 Document C1 - C3 Alkyl, R3 Hydrogen.

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