581098-30-8

Basic information

• Product Name: Ethanedione, (2-bromo-4-pyridinyl)(4-fluorophenyl)-, 1-oxime
• Synonyms: 2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)-ethan-1,2-dion-2-oxime;1-(2-Bromo-pyridin-4-yl)-2-(4-fluoro-phenyl)-ethane-1,2-dione 1-oxime;1-(2-bromopyridin-4-yl)-2-(4-fluorophenyl)-ethane-1,2-dione-1-oxime
• CAS NO: 581098-30-8
• Molecular Formula: C13H8BrFN2O2
• Molecular Weight: 323.121
• Mol File: 581098-30-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 214 °C
• Boiling Point: 470.5±45.0 °C(Predicted)
• Density: 1.58±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Ethanedione, (2-bromo-4-pyridinyl)(4-fluorophenyl)-, 1-oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanedione, (2-bromo-4-pyridinyl)(4-fluorophenyl)-, 1-oxime(581098-30-8)
• EPA Substance Registry System: Ethanedione, (2-bromo-4-pyridinyl)(4-fluorophenyl)-, 1-oxime(581098-30-8)

Safety Data

• Hazardous Substances Data: 581098-30-8(Hazardous Substances Data)

Upstream product

• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 4926-28-7 2-Bromo-4-picoline 
• 158876-70-1 2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)ethan-1-one 
• 116332-54-8 4-fluoro-N-methoxy-N-methylbenzamide 

Downstream Products

• 581098-36-4 2-amino-2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)-ethanone hydrochloride 

Relevant articles and documents

Unexpected reaction of 2-alkylsulfanylimidazoles to imidazol-2-ones: Pyridinylimidazol-2-ones as novel potent P38α mitogen-activated protein kinase inhibitors

While optimizing the synthesis of 2-alkylsulfanyl-5-(2-aminopyridin-4-yl) imidazoles, we identified an unexpected reaction to pyridinylimidazol-2-ones. 2-Alkylsulfanylimidazoles, bearing a 2-hydroxyethyl or a 2,3-dihydroxypropyl moiety at the imidazole C2-S position, were converted by heating into imidazol-2-ones. These imidazol-2-ones were tested for their ability to inhibit p38α MAP kinase and LPS-stimulated TNF-α release in HWB. Introduction of an amino moiety at the pyridine C2 position led to compounds showing potent enzyme inhibitory activity with double-digit nanomolar IC 50 values (5a: IC50 = 23 nM).

2-THIO-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE IN PHARMACEUTICS

The invention relates to 2-thio-substituted imidazole derivatives of formula (I), wherein the radicals R1, R2, R3 and m have the meanings as cited in the description. The inventive compounds comprise an immunomodulatory action and/or an action that inhibits the release of cytokines and are thus suited for treating diseases associated with a disorder of the immune system.