957187-27-8

Basic information

• Product Name: 8-Bromo-6-chloroimidazo[1,2-a]pyridine
• Synonyms: 8-Bromo-6-chloroimidazo[1,2-a]pyridine;IMidazo[1,2-a]pyridine, 8-broMo-6-chloro-;6-chloro-8-bromoimidazo[1,2-a]pyridine
• CAS NO: 957187-27-8
• Molecular Formula: C₇H₄BrClN₂
• Molecular Weight: 231.48
• Mol File: 957187-27-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 125-128℃
• Appearance: /
• Density: 1.84 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 8-Bromo-6-chloroimidazo[1,2-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Bromo-6-chloroimidazo[1,2-a]pyridine(957187-27-8)
• EPA Substance Registry System: 8-Bromo-6-chloroimidazo[1,2-a]pyridine(957187-27-8)

Safety Data

• Hazardous Substances Data: 957187-27-8(Hazardous Substances Data)

Usage

Uses

8-Bromo-6-chloroimidazo[1,2-a]pyridine is used as an organic chemical synthesis intermediate.

Upstream product

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Relevant articles and documents

Antikinetoplastid SAR study in 3-nitroimidazopyridine series: Identification of a novel non-genotoxic and potent anti-T. b. brucei hit-compound with improved pharmacokinetic properties

To study the antikinetoplastid 3-nitroimidazo[1,2-a]pyridine pharmacophore, a structure-activity relationship study was conducted through the synthesis of 26 original derivatives and their in vitro evaluation on both Leishmania spp and Trypanosoma brucei brucei. This SAR study showed that the antitrypanosomal pharmacophore was less restrictive than the antileishmanial one and highlighted positions 2, 6 and 8 of the imidazopyridine ring as key modulation points. None of the synthesized compounds allowed improvement in antileishmanial activity, compared to previous hit molecules in the series. Nevertheless, compound 8, the best antitrypanosomal molecule in this series (EC50 = 17 nM, SI = 2650 & E° = ?0.6 V), was not only more active than all reference drugs and previous hit molecules in the series but also displayed improved aqueous solubility and better in vitro pharmacokinetic characteristics: good microsomal stability (T1/2 > 40 min), moderate albumin binding (77%) and moderate permeability across the blood brain barrier according to a PAMPA assay. Moreover, both micronucleus and comet assays showed that nitroaromatic molecule 8 was not genotoxic in vitro. It was evidenced that bioactivation of molecule 8 was operated by T. b. brucei type 1 nitroreductase, in the same manner as fexinidazole. Finally, a mouse pharmacokinetic study showed that 8 displayed good systemic exposure after both single and repeated oral administrations at 100 mg/kg (NOAEL) and satisfying plasmatic half-life (T1/2 = 7.7 h). Thus, molecule 8 appears as a good candidate for initiating a hit to lead drug discovery program.

BICYCLIC PIPERAZINE COMPOUNDS

Bicyclic piperazine compounds of Formula I are provided, including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.