52559-17-8

Basic information

• Product Name: 6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine
• Synonyms: 4-Amino-6-chloro-3H-imidazo[4,5-c]pyridine;6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine;3H-IMidazo[4,5-c]pyridin-4-aMine, 6-chloro-
• CAS NO: 52559-17-8
• Molecular Formula: C6H5ClN4
• Molecular Weight: 168.5837
• Mol File: 52559-17-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine(52559-17-8)
• EPA Substance Registry System: 6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine(52559-17-8)

Safety Data

• Hazardous Substances Data: 52559-17-8(Hazardous Substances Data)

Usage

General Description

6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine is a chemical compound with the molecular formula C7H5ClN4. It belongs to the class of organic compounds known as polycyclic aromatic compounds. These are aromatic compounds containing three or more separate aromatic rings. They are produced by incomplete combustion of organic materials or by pyrolysis of hydrocarbons. 6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine in particular contains an imidazopyridine moiety, which makes it an integral component in medicinal chemistry due to its useful biological activities. However, specific details regarding its role or application in medicinal chemistry, its properties, or its safety profile are not widely available in the scientific literature.

InChI:InChI=1S/C6H5ClN4/c7-4-1-3-5(6(8)11-4)10-2-9-3/h1-2H,(H2,8,11)(H,9,10)

Upstream product

• 6811-77-4 3-deazaadenine 
• 2589-12-0 4,6-dichloro-1H-imidazo<4,5-c>pyridine 
• 2402-78-0 2,6-dichloropyridine 
• 101079-63-4 3,4-diamino-2,6-dichloropyridine 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 2587-03-3 2,6-dichloro-N-nitro-4-pyridinamine 
• 2897-43-0 2,6-dichloro-3-nitropyridin-4-amine 
• 25194-01-8 4-nitro-2,6-dichloro-pyridine 
• 2587-02-2 2,6-dichloro-[4]pyridylamine 
• 668268-66-4 3-amino-4-acetamido-2,6-dichloropyridine 

Downstream Products

• 6811-77-4 3-deazaadenine 
• 668268-64-2 8-chloro-3-deazaadenine 
• 668268-69-7 3-chloro-3-deazaadenine 

Relevant articles and documents

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.