1027159-01-8

Basic information

• Product Name: 3H-IMidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-diMethylethyl ester
• Synonyms: 3H-IMidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-diMethylethyl ester;tert-Butyl 2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridine-3-carboxylate;tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate
• CAS NO: 1027159-01-8
• Molecular Formula: C₁₁H₁₃N₃O₃
• Molecular Weight: 235.23922
• Mol File: 1027159-01-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3H-IMidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-IMidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-diMethylethyl ester(1027159-01-8)
• EPA Substance Registry System: 3H-IMidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-diMethylethyl ester(1027159-01-8)

Safety Data

• Hazardous Substances Data: 1027159-01-8(Hazardous Substances Data)

Usage

General Description

3H-Imidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-dimethylethyl ester, also known as TAK-242, is a chemical compound that is commonly used in research as an inhibitor of toll-like receptor signaling. 3H-Imidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-dimethylethyl ester is a synthetic small-molecule inhibitor that has been shown to block the production of pro-inflammatory cytokines in response to toll-like receptor stimulation, making it a promising candidate for the treatment of inflammatory diseases. Its 1,1-dimethylethyl ester form is often used to enhance its activity and stability in experimental settings. Additionally, TAK-242 has been investigated for its potential use in combating various diseases, including sepsis, rheumatoid arthritis, and other inflammatory conditions.

Upstream product

• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 452-58-4 2,3-Diaminopyridine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 103409-28-5 2,3-Dihydro-2-oxo-1H-imidazo<4,5-b>pyridine-1-carboxylic acid ethyl ester 
• 16328-62-4 1,3-dihydro-imidazo[4,5-b]pyridin-2-one 

Downstream Products

• 1026005-26-4 1-Cyclohexylmethyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridine-3-carboxylic acid tert-butyl ester 
• 1027318-83-7 1-Benzyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Rational Design, Pharmacomodulation, and Synthesis of Dual 5-Hydroxytryptamine 7 (5-HT7)/5-Hydroxytryptamine 2A (5-HT2A) Receptor Antagonists and Evaluation by [18F]-PET Imaging in a Primate Brain

We report the synthesis of 46 tertiary amine-bearing N-alkylated benzo[d]imidazol-2(3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, oxazolo[4,5-b]pyridin-2(3H)-ones and N,N′-dialkylated benzo[d]imidazol-2(3H)-ones. These compounds were evaluated against 5-HT7R, 5-HT2AR, 5-HT1AR, and 5-HT6R as potent dual 5-HT7/5-HT2A serotonin receptors ligands. A thorough study of the structure-activity relationship of the aromatic rings and their substituents, the alkyl chain length and the tertiary amine was conducted. 1-(4-(4-(4-Fluorobenzoyl)piperidin-1-yl)butyl)-1H-benzo[d]imidazol-2(3H)-one (79) and 1-(6-(4-(4-fluorobenzoyl)piperidin-1-yl)hexyl)-1H-benzo[d]imidazol-2(3H)-one (81) were identified as full antagonist ligands on cyclic adenosine monophosphate (cAMP, KB = 4.9 and 5.9 nM, respectively) and inositol monophosphate (IP1, KB = 0.6 and 16 nM, respectively) signaling pathways of 5-HT7R and 5-HT2AR. Both antagonists crossed the blood-brain barrier as evaluated with [18F] radiolabeled compounds [18F]79 and [18F]81 in a primate's central nervous system using positron emission tomography. Both radioligands showed standard uptake values ranging from 0.8 to 1.1, a good plasmatic stability, and a distribution consistent with 5-HT7R and 5-HT2AR in the CNS.