3-Methyl-3H-imidazo[4,5-b]pyridin-6-ol

Imidazo[4,5-b] pyridine derivatives was often defined as a precursor in thesynthesis of a variety of therapeutic agents. Indeed, heterocyclic compoundscontaining this motif are endowed with anticancer activity (Guo , 2005), antibacterial (Aridoss , 2006),tuberculostatic(Bukowski , 1989) and antimitotic activity (Temple,1990).

Synthesis of 7-substituted imidazo[4,5-b]pyridine derivatives 7a–e is shown in Scheme 1

To a solution of the 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine(0.3 g, 1.09 mmol), potassium carbonate (0.2 g, 1.42 mmol) andtetra-n-butylammonium bromide (0.04 g, 0.1 mmol) in DMF (15 ml) was addedmethyl iodide (0.08 ml, 1.31 mmol). Stirring was continued at room temperaturefor 12 h. The salt was removed by filtration and the filtrate concentratedunder reduced pressure. The residue was separated by chromatography on acolumn of silica gel with ethyl acetate/hexane (1/2) as eluent. The compoundwas recrystallized from ethanol.


3-Methyl-3H-imidazo[4,5-b]pyridine AldrichCPR | Sigma-Aldrich

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To a solution 6-bromo-2-phenyl-1-imidazo[4,5-]pyridine (0.30 g,1.1 mmol), potassium carbonate (0.20 g, 1.42 mmol) andtetra--butylammonium bromide 0.035 g (0,11 mmol) in DMF (15 ml) wasadded ethyl 2-bromoacetate (0.14 ml, 1.30 mmol). Stirring was continued atroom temperature for 12 h. The salt was removed by filtration and the filtrateconcentrated under reduced pressure. The residue was separated bychromatography on a column of silica gel with ethyl acetate/hexane (1/2) aseluent. Reddish crystals were isolated when the solvent was allowed toevaporate (yield = 28%)


-7-piperazin-1-yl-3H-imidazo[4,5-b]pyridine (7) ..

Here, we wish to report a novel route leading to 3-benzyl-6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one. We have checked the action ofbenzyl chloride towards 6-bromo-1,3-dihydro-imidazo[4,5 - b-]pyridin-2- oneusing K2CO3 as base (schem1).

3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridine | …

For background regarding biological activity of imidazo[4,5-b]pyridines, see: Cristalli et al. (1995); Bukowski & Kaliszan (1991); Aridoss et al. (2006); Bavetsias et al. (2007). For background to their pharmacological activity, see: Chen & Dost (1992); Weier et al. (1993).

-3H-imidazo[4,5-b]-pyridine-6-carboxylic acid ..

The imidazopyridine moieties are important pharmacophores, which have proven tobe useful for a number of biologically relevant targets. The compounds derivedfrom the imidazopyridine system have recently been evaluated as antagonists ofvarious biological receptors, including angiotensin-II (Chen et al.,1992; Cappelli et al., 2006), platelet activating factor(Weier etal., 1994), and metabotropic glutamate subtype V (Kulkarni etal.,2007). Recently, a series of imidazo[4,5-b] pyridine derivativesasorally bioavailable Aurora A inhibitors with excellent potencies were reported(Bavetsias et al., 2007; Bavetsias et al., 2010)Hence, thesynthesis of imidazo[4,5-b]pyridine derivatives is currently of greatinterest. Despite the importance of these intermediates, the methodologyavailable for the synthesis was generally target-specific and restrictive intheir scope.

New Derivatives of 1H-imidazo[4,5-b]pyridine-2(3H)- …

An attempt tried for in-silico design of title compounds aiming to inhibit lumazine synthase. Binding interaction of test motifs studied using crystal protein lumazine synthase from M. tuberculosis (PDB 2C92).[] With the aim of rationalizing the antimicrobial activity data obtained, docking study was performed for the imidazo [4,5-b] pyridine derivatives 1a-1l and 2a-2j in order to investigate the possible interactions with lumazine synthase. Minimum docking score for test ligands was showed in in comparison with the reference ligand Trimethoprim.