132898-03-4

Usage

Uses

Used in Pharmaceutical Industry:
1H-Imidazo[4,5-b]pyridin-2-amine(9CI) is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique structure and properties make it a valuable building block for the development of new compounds with therapeutic potential.
Used in Agrochemical Industry:
1H-Imidazo[4,5-b]pyridin-2-amine(9CI) is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of new compounds for agricultural applications.
Used in Kinase Inhibitor Research:
1H-Imidazo[4,5-b]pyridin-2-amine(9CI) is used as a kinase inhibitor in biological research. Its potential to inhibit kinase activity makes it a promising candidate for the development of targeted therapies for various diseases, including cancer.
Used in Anti-Cancer Drug Development:
1H-Imidazo[4,5-b]pyridin-2-amine(9CI) is used as an anti-cancer agent in the development of new drugs. Its potential biological activities, such as inhibiting cancer cell growth and proliferation, make it a valuable compound for the creation of novel therapeutic agents.

InChI:InChI=1/C6H6N4/c7-6-9-4-2-1-3-8-5(4)10-6/h1-3H,(H3,7,8,9,10)

Upstream product

• 790664-95-8 (Z)-[3-(2-amino-1H-imidazol-4-yl)allyl]carbamic acid methyl ester 
• 452-58-4 2,3-Diaminopyridine 
• 506-68-3 bromocyane 
• 36649-01-1 ethyl (3H-imidazo[4,5-b]pyridin-2-yl)carbamate 
• 33707-36-7 1-(methoxycarbonyl)-1,2-dihydropyridine 
• 110-86-1 pyridine 

Downstream Products

• 1616406-44-0 2-(2-amino-3H-imidazo[4,5-b]pyridin-3-yl)-1-(2,3-dichlorophenyl)ethanone 
• 1616406-45-1 C₁₄H₁₀Cl₂N₄O 

Relevant academic research and scientific papers

Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids: Ab initio calculations, tautomerism, and reactivity

(Chemical Equation Presented) A simple synthesis of the fused tetrahydro-imidazopyridine 13 was accomplished via selective addition of protected guanidine to N-carbomethoxy-1,2-dihydropyridine in the presence of bromine. Base-mediated semicleavage of the aminal gave 4-substituted 2-aminoimidazole 14. With this new method, natural marine metabolite 3-amino-1-(2-aminoimidazol-4-yl)-prop-1-ene (1) and derivatives may now be prepared from pyridine. Ab initio calculations of the energies of tautomers I-IV and deuteration experiments have provided insight into their reactivity.

Discovery and development of 2-aminobenzimidazoles as potent antimalarials

The emergence of Plasmodium falciparum resistance to frontline antimalarials, including artemisinin combination therapies, highlights the need for new molecules that act via novel mechanisms of action. Herein, we report the design, synthesis and antimalarial activity of a series of 2-aminobenzimidazoles, featuring a phenol moiety that is crucial to the pharmacophore. Two potent molecules exhibited IC50 values against P. falciparum 3D7 strain of 42 ± 4 (3c) and 43 ± 2 nM (3g), and high potency against strains resistant to chloroquine (Dd2), artemisinin (Cam3.IIC580Y) and PfATP4 inhibitors (SJ557733), while demonstrating no cytotoxicity against human cells (HEK293, IC50 > 50 μM). The most potent molecule, possessing a 4,5-dimethyl substituted phenol (3r) displayed an IC50 value of 6.4 ± 0.5 nM against P. falciparum 3D7, representing a 12-fold increase in activity from the parent molecule. The 2-aminobenzimidazoles containing a N1-substituted phenol represent a new class of molecules that have high potency in vitro against P. falciparum malaria and low cytotoxicity. They possessed attractive pharmaceutical properties, including low molecular weight, high ligand efficiency, high solubility, synthetic tractability and low in vitro clearance in human liver microsomes.

Copper-catalyzed sequential N-arylation of C-amino-NH-azoles

Copper(ii)-catalyzed boronic acid promoted C-N bond cross-coupling reactions have been successfully developed for sequential N-arylation of C-amino-NH-azoles. These general protocols are compatible with a variety of aryl/hetero-aryl boronic acids and provided rapid access to a diverse array of diarylaminoazole derivatives in a two-step sequence or in one-pot. This journal is

Synthesis of substituted heterocyclic compounds

The invention relates to a method of synthesizing heterocyclic compounds. The invention is characterised in that it consists in opening a compound having formula (I), wherein: —X represents NH, O, S or a N-p group, p being a protective group, such as Boc

Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4

High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.