52090-89-8

Basic information

• Product Name: 5-CHLORO-3H-IMIDAZO[4,5-B]PYRIDINE
• Synonyms: 5-CHLORO-3H-IMIDAZO[4,5-B]PYRIDINE;5-Chloro-3H-imidazo[4,5-b...;3H-IMidazo[4,5-b]pyridine, 5-chloro-
• CAS NO: 52090-89-8
• Molecular Formula: C₆H₄ClN₃
• Molecular Weight: 153.57
• EINECS: 1592732-453-0
• Product Categories: Heterocycle-Pyridine series
• Mol File: 52090-89-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 415.1 °C at 760 mmHg
• Flash Point: 237.3 °C
• Appearance: /
• Density: 1.531 g/cm³
• Vapor Pressure: 1.02E-06mmHg at 25°C
• Refractive Index: 1.72
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.53±0.40(Predicted)
• CAS DataBase Reference: 5-CHLORO-3H-IMIDAZO[4,5-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-3H-IMIDAZO[4,5-B]PYRIDINE(52090-89-8)
• EPA Substance Registry System: 5-CHLORO-3H-IMIDAZO[4,5-B]PYRIDINE(52090-89-8)

Safety Data

• Hazardous Substances Data: 52090-89-8(Hazardous Substances Data)

Usage

General Description

5-chloro-3H-imidazo[4,5-b]pyridine is a chemical compound with the molecular formula C7H5ClN2. It is a heterocyclic compound that consists of a fused imidazole and pyridine ring system. 5-chloro-3H-imidazo[4,5-b]pyridine is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential biological activities, including its role as an anti-tumor, anti-inflammatory, and anti-viral agent. The presence of the chloro group on the imidazole ring gives the compound unique reactivity and functionalization properties, making it a useful building block in organic synthesis. Overall, 5-chloro-3H-imidazo[4,5-b]pyridine is an important chemical compound with diverse applications in the fields of medicine and agriculture.

InChI:InChI=1/C6H4ClN3/c7-5-2-1-4-6(10-5)9-3-8-4/h1-3H,(H,8,9,10)

Upstream product

• 40851-95-4 6-chloropyridine-2,3-diamine 
• 64-18-6 formic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 
• 149-73-5 trimethyl orthoformate 
• 273-21-2 3H-imidazo[4,5-b]pyridine 
• 6863-46-3 3H-Imidazo<4,5-b>pyridine 4-N-oxide 
• 6863-46-3 Imidazo<4,5-b>pyridine 4-Oxide 

Downstream Products

• 83472-65-5 5-chloro-3-methyl-3H-imidazo[4,5-b]pyridine 

Relevant articles and documents

NOVEL INHIBITORS OF BACTERIAL GLUTAMINYL CYCLASES FOR USE IN THE TREATMENT OF PERIODONTAL AND RELATED DISEASES

The present invention relates to novel compounds which are particularly useful as inhibitors of bacterial glutaminyl cyclases (bacQC); pharmaceutical compositions comprising such compounds; compounds and/or pharmaceutical compositions for use in methods for treatment, in particular for use in the treatment of periodontitis and related conditions; as well as to crystals comprising bacterial glutaminyl cyclases, methods for identifying candidate compounds which may associate with the binding pocket of a bacQC and/or are bacQC inhibitors.

Microwave-Assisted C-2 Direct Alkenylation of Imidazo[4,5-b]pyridines: Access to Fluorescent Purine Isosteres with Remarkably Large Stokes Shifts

We describe herein the first C-2 direct alkenylation of the valuable 3H-imidazo[4,5-b]pyridine promoted by microwave-assisted Pd/Cu co-catalysis. The reaction is rapid and compatible with a wide range of functional groups either on the imidazo[4,5-b]pyridine ring or on the styryl bromides thereby leading to the isolation of 23 compounds with moderate to good yields. The relevance of this method is demonstrated by its application to the synthesis of new cross-conjuguated push-pull 2-vinyl- and 2-alkynylimidazo[4,5-b]pyridines characterized by satisfactory fluorescence quantum yields and remarkable solvatofluorochromic properties.

Structure-based design and synthesis of the first weak non-phosphate inhibitors for IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis

In this paper, we describe the structure-based design, synthesis, and biological evaluation of cytosine derivatives and analogues that inhibit IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. This pathway is responsible for the biosynthesis of the C5 precursors to isoprenoids, isopentenyl diphosphate (IPP, 1) and dimethylallyl diphosphate (DMAPP, 2; Scheme 1). The non-mevalonate pathway is the sole source for 1 and 2 in the protozoan Plasmodium parasites. Since mammals exclusively utilize the alternative mevalonate pathway, the enzymes of the non-mevalonate pathway have been identified as attractive new drug targets in the fight against malaria. Based on computer modeling (cf. Figs. 2 and 3), new cytosine derivatives and analogues (Fig. 1) were selected as potential drug-like inhibitors of IspF protein, and synthesized (Schemes 2-5). Determination of the enzyme activity by 13C-NMR spectroscopy in the presence of the new ligands showed inhibitory activities for some of the prepared cytosine and pyridine-2,5-diamine derivatives in the upper micromolar range (IC50 values; Table). The data suggest that it is possible to inhibit IspF protein without binding to the polar diphosphate binding site and the side chain of Asp56′, which interacts with the ribose moiety of the substrate and substrate analogues. Furthermore, a new spacious sub-pocket was discovered which accommodates aromatic spacers between cytosine derivatives or analogues (binding to 'Pocket III') and rings that occupy the flexible hydrophobic region of 'Pocket II'. The proposed binding mode remains to be further validated by X-ray crystallography.