28279-49-4

Usage

Uses

Used in Pharmaceutical Research:
6-BROMO-4H-IMIDAZO[4,5-B]PYRIDINE is used as a building block for the synthesis of various biologically active compounds, contributing to the development of new pharmaceutical agents.
Used in Drug Development:
6-BROMO-4H-IMIDAZO[4,5-B]PYRIDINE is utilized in the development of novel drugs, leveraging its versatile reactivity and potentially valuable properties to create innovative therapeutic agents.
Used in Agrochemicals:
6-BROMO-4H-IMIDAZO[4,5-B]PYRIDINE is employed in the creation of new agrochemicals, where its unique chemical structure can be harnessed to develop effective products for agricultural applications.
Used in Anti-Cancer Research:
6-BROMO-4H-IMIDAZO[4,5-B]PYRIDINE is studied for its potential use as an anti-cancer agent, with research indicating its ability to inhibit certain enzymes and receptors associated with cancer progression, offering a promising avenue for cancer treatment.
Used in Enzyme and Receptor Inhibition:
6-BROMO-4H-IMIDAZO[4,5-B]PYRIDINE is used in the inhibition of specific enzymes and receptors, which may play a role in cancer development and progression, thereby providing a potential therapeutic approach to combat cancer.

InChI:InChI=1/C6H4BrN3/c7-4-1-5-6(8-2-4)10-3-9-5/h1-3H,(H,8,9,10)

Upstream product

• 38875-53-5 5-bromo-pyridine-2,3-diamine 
• 64-18-6 formic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 124-38-9 carbon dioxide 
• 273-21-2 3H-imidazo[4,5-b]pyridine 
• 6945-68-2 5-bromo-3-nitro-pyridin-2-ylamine 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 83472-57-5 6-Bromoimidazo<4,5-b>pyridine 4-Oxide 
• 93752-20-6 6-bromo-1H-imidazo[4,5-b]pyridine-2(3H)-thione 
• 1254697-46-5 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo [4,5-b]pyridine 
• 37805-78-0 6-bromo-3-methylimidazo<4,5-b>pyridine 
• 166047-14-9 6-bromo-1-methylimidazo<4,5-b>pyridine 
• 77862-95-4 methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate 

Relevant academic research and scientific papers

Design, synthesis, biological evaluation and cellular imaging of imidazo[4,5-b]pyridine derivatives as potent and selective TAM inhibitors

The TAM kinase family arises as a new effective and attractive therapeutic target for cancer therapy, autoimmune and viral diseases. A series of 2,6-disubstituted imidazo[4,5-b]pyridines were designed, synthesized and identified as highly potent TAM inhib

Halogenation of 2-unsubstituted and 2-methylimidazo[4,5-b]pyridine derivatives

Halogenation of 2-unsubstituted and 2-methylimidazo[4,5-b]pyridines and their N-methyl derivatives with bromine and chlorine in acetic acid takes different pathways, depending on the acetic acid concentration. The bromination in 50% aqueous acetic acid gives only 6-bromoimidazo[4,5-b]pyridines; bromination and chlorination of 2-unsubstituted imidazo[4,5-b]pyridines in glacial acetic acid leads to 5,6-dibromo(dichloro)imidazo[4,5-b]pyridin-2-ones, and bromination of 2-methylimidazo[4,5-b]pyridines in glacial acetic acid involves both the pyridine ring and the 2-methyl group to afford the corresponding 6-bromo-2-tribromomethylimidazo[4,5-b]pyridines.

Synthesis, biological properties and structural study of new halogenated azolo[4,5-b]pyridines as inhibitors of CK2 kinase

The new halogenated 1H-triazolo[4,5-b]pyridines and 1H-imidazo[4,5-b]pyridines were synthesised as analogues of known CK2 inhibitors: 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt) and 4,5,6,7-tetrabromo-1H-benzimidazole (TBBi). Their influence on the activity of recombinant human CK2α, CK2α’ and PIM1 kinases was determined. The most active inhibitors were di- and trihalogenated 1H-triazolo[4,5-b]pyridines (4a, 5a and 10a) with IC50 values 2.56, 3.82 and 3.26 μM respectively for CK2α. Furthermore, effect on viability of cancer cell lines MCF-7 (human breast adenocarcinoma) and CCRF-CEM (T lymphoblast leukemia) of all final compounds was evaluated. Finally, three crystal structures of complexes of CK2α1-335 with inhibitors 4a, 5a and 10a were obtained. In addition, new protocol was used to obtain high-resolution crystal structures of CK2α’Cys336Ser in complex with four inhibitors (4a, 5a, 5b, 10a).

Convenient synthesis of imidazo[1,5-a]pyrimidine derivatives and their unusual recyclization into 3H-imidazo[4,5-b]pyridine derivatives

[Figure not available: see fulltext.] New derivatives of imidazo[1,5-a]pyrimidine have been synthesized by cyclization of in situ generated 1H-imidazol-4(5)-amine with 1,3-diketones or malondialdehyde derivatives. Utilization of asymmetrical 1,3-diketones leads to the formation of a mixture of regioisomers. The discovered conversion of imidazo[1,5-a]pyrimidine core into 3H-imidazo[4,5-b]pyridine that takes place only under acidic conditions can be considered as a new version of Dimroth rearrangement involving cleavage of C–N bond and formation of C–C bond.

Cu@U-g-C3N4 Catalyzed Cyclization of o-Phenylenediamines for the Synthesis of Benzimidazoles by Using CO2 and Dimethylamine Borane as a Hydrogen Source

Abstract: This work reports a green and sustainable route for the synthesis of benzimidazoles via C–N bond formation using carbon dioxide (CO2) as a C1 carbon source. In this work, Cu@U-g-C3N4 catalyst was prepared from urea derived porous graphitic carbon?nitride (U-g-C3N4) and CuCl2 and characterized by FT-IR, XRD, XPS, SEM, TPD etc. The Cu@U-g-C3N4 as a heterogeneous recyclable catalyst has been employed first time for the cyclization of o-phenylenediamines (OPD) with CO2 to benzimidazoles using dimethylamine borane (DMAB). The proposed protocol becomes sustainable and efficient due to the use of propylene carbonate/water as a suitable biodegradable, economical and environmentally benign solvent system. The proposed catalytic system showed a wide range of substrate scope for the synthesis of benzimidazoles in good to excellent yields. Graphical Abstract: [Figure not available: see fulltext.]

TRICYCLIC DLK INHIBITORS AND USES THEREOF

The invention relates to compounds of formula (I) and salts thereof, wherein ring A and R1-R2 have any of the values defined in the specification. The compounds and salts are useful for treating DLK mediated disorders. The invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable salt thereof, as well as methods of using said compounds, salts, or compositions as DLK inhibitors and for treating neurodegeneration diseases and disorders.

HETEROCYCLIC COMPOUNDS AND USE THEREOF AS MODULATORS OF TYPE III RECEPTOR TYROSINE KINASES

Provided herein are heterocyclic compounds for treatment of CSF1R, FLT3, KIT, and/or PDGFRβ kinase mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.

2-AMINO-BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS 5-LIPOXYGENASE AND/OR PROSTAGLANDIN E SYNTHASE INHIBITORS

The present invention relates to benzimidazole derivatives having the general formula I, wherein n is 0 or 1; X1 and X2 are independently, at each occurrence, CR5 or N; Y is C1-C6 alkylene, wherein alkylene is optionally substituted with one to two C1-C3 alkyl groups; R1 is selected from the group consisting of hydrogen, halogen, C1-C6 alkoxy, -NH2, -NHR6, -NR7R8 and -NH-(R9)n-R10, n being 0 or 1; R2 is selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, -NH2, -NHR6, - NR7R8 and -NH-(R9)n-R10; R3 is selected from the group consisting of hydrogen, hydroxyl, OR11, -NR7R8, C1-C6 alkoxy, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C3 haloalkyl, -C(O)NHR11, aryl, heteroaryl and heterocyclyl, wherein each of said cycloalkyl, aryl, heteroaryl and heterocyclyl is optionally and independently substituted with one to four Ra groups; and R4 is selected from the group consisting of -NH2, -N(R12)(V)pR13, - NH(V)p-OR14, -NHC(O)R15, and groups of formula la shown below, and their use in the treatment of diseases, in particular inflammatory diseases, cancer, stroke and/or Alzheimer's disease.

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.