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Usage

Derivative of imidazo[4,5-b]pyridine

A heterocyclic compound 1H-Imidazo[4,5-b]pyridin-2-amine,1-methyl- is derived from imidazo[4,5-b]pyridine, which is a heterocyclic compound containing an imidazole ring fused to a pyridine ring.

Heterocyclic ring system

Potential pharmaceutical importance The presence of a heterocyclic ring system in 1H-Imidazo[4,5-b]pyridin-2-amine,1-methyl- makes it potentially important in the pharmaceutical industry.

Building block in synthesis

Biologically active compounds Due to its structure, 1H-Imidazo[4,5-b]pyridin-2-amine,1-methylcan be used as a building block in the synthesis of various biologically active compounds.

Applications in medicinal chemistry

Development of new drugs This chemical compound may have applications in the field of medicinal chemistry, particularly for the development of new drugs.

Methyl group attachment

Nitrogen atom in the imidazole ring In the structure of 1H-Imidazo[4,5-b]pyridin-2-amine,1-methyl-, a methyl group is attached to the nitrogen atom in the imidazole ring, which may influence its chemical properties and reactivity.

Upstream product

• 506-68-3 bromocyane 
• 56291-51-1 2-amino-3-methylaminopyridine 
• 50339-06-5 1-methyl-1,3-dihydro-2H-imidazo<4,5-b>pyridin-2-one 
• 13534-99-1 2-Amino-3-bromopyridine 
• 39998-52-2 1-methyl-1H-imidazo[4,5-b]pyridine 
• 13269-19-7 3-amino-2-nitropyridine 
• 54231-35-5 3-fuoro-2-nitropyridine 
• 32605-06-4 3-(N-methylamino)-2-nitropyridine 
• 1451999-14-6 C₇H₆BrN₃ 
• 65550-24-5 2-chloro-1-methyl-1H-imidazo[4,5-b]pyridine 

Relevant academic research and scientific papers

Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase

In order to explore the interactions of bisphosphonate ligands with the active site and an allosteric pocket of the human farnesyl pyrophosphate synthase (hFPPS), substituted indole and azabenzimidazole bisphosphonates were designed as chameleon ligands. NMR and crystallographic studies revealed that these compounds can occupy both sub-pockets of the active site cavity, as well as the allosteric pocket of hFPPS in the presence of the enzyme's Mg2+ ion cofactor. These results are consistent with the previously proposed hypothesis that the allosteric pocket of hFPPS, located near the active site, plays a feed-back regulatory role for this enzyme.

Cross-coupling reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine offers a new synthetic route to mutagenic heterocyclic amine-PHIP and DMIP

A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.

Synthesis and mutagenic potency of structural isomers of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

(Chemical Equation Presented) Synthesis of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP), three structural isomers, and two desphenyl PhIP congeners has been carried out. Mutagenic potency was evaluated using S. typhimurium strain TA98 in the Ames test. Mutagenic potency increased in relation to structural features in these heterocyclic amines that allow extended resonance between the phenyl and imidazo[4,5-b]pyridine N2-amino substituents. By contrast, PhIP isomers, whose substitution disallows involvement of the phenyl group in their ammoimidazo resonance hybrids, and desphenyl congeners were from 86- to 234-fold less mutagenic than PhIP.