52090-89-8

Usage

Uses

Used in Pharmaceutical Industry:
5-chloro-3H-imidazo[4,5-b]pyridine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into the molecular structures of drugs, enhancing their therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical field, 5-chloro-3H-imidazo[4,5-b]pyridine is utilized as an intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Organic Synthesis:
5-chloro-3H-imidazo[4,5-b]pyridine is employed as a building block in organic synthesis due to its unique reactivity, allowing for the creation of a variety of complex organic compounds for different applications.
Used in Biological Research:
5-chloro-3H-imidazo[4,5-b]pyridine is used as a subject of biological research for its potential as an anti-tumor, anti-inflammatory, and anti-viral agent, with ongoing studies aimed at understanding and harnessing its therapeutic properties.

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

Downstream Products

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

Relevant academic research and scientific papers

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.

5. 7 - Dichloro - 1 H - imidazo [4, 5 - B] pyridine synthesis method

The invention discloses a method for synthesizing 5,7-dichloro-1H-imidazo-[4,5-B] pyridine. The method comprises steps as follows: in the presence of ammonium chloride, ethyl acetate and water, a compound 1 is reduced by iron powder to obtain a compound 2; the compound 2 has a reflux reaction with p-toluenesulfonic acid monohydrate and triethyl orthoformate to obtain a compound 3; acetic acid is taken as a solvent, the compound 3 reacts with m-chloroperoxybenzoic acid to a compound 4; the compound 4 has a reflux reaction with phosphorus oxychloride at the temperature of 0-5 DEG C in the presence of DMF (Dimethyl formamide) so as to obtain 5,7-dichloro-1H-imidazo-[4,5-B] pyridine. A brand-new synthesis path of 5,7-dichloro-1H-imidazo-[4,5-B] pyridine is provided, raw materials are easy to obtain, the preparation process is simple, the yield is high, the cost is low, and large-scale production can be realized.

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.

Direct Alkynylation of 3H-Imidazo[4,5-b]pyridines Using gem-Dibromoalkenes as Alkynes Source

C2 direct alkynylation of 3H-imidazo[4,5-b]pyridine derivatives is explored for the first time. Stable and readily available 1,1-dibromo-1-alkenes, electrophilic alkyne precursors, are used as coupling partners. The simple reaction conditions include an inexpensive copper catalyst (CuBr·SMe2 or Cu(OAc)2), a phosphine ligand (DPEphos) and a base (LiOtBu) in 1,4-dioxane at 120 °C. This C-H alkynylation method revealed to be compatible with a variety of substitutions on both coupling partners: heteroarenes and gem-dibromoalkenes. This protocol allows the straightforward synthesis of various 2-alkynyl-3H-imidazo[4,5-b]pyridines, a valuable scaffold in drug design.

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.

Derivatives of erythromycin, their preparation process and their use as medicaments

A compound of the formula wherein X=CH2or NH, Y=H or Hal, Z=H or acyl of an organic carboxylic acid of 1 to 6 carbon atoms, R is W and W′ are individually H, Hal and alkyl of 1 to 8 carbon atoms optionally substituted by at least one halogen having antibiotic properties.