1176664-83-7

Upstream product

• 31562-99-9 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine 
• 107-21-1 ethylene glycol 
• 504-29-0 2-aminopyridine 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 426239-77-2 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 

Downstream Products

• 1417910-26-9 C₁₅H₁₃N₅O 
• 1417910-44-1 2-(4-methoxyphenyl)-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-1H-imidazo[1,2-a]pyridine 
• 1417910-46-3 3-((4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(4-methoxyphenyl)-1H-imidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

Structural modification of zolpidem led to potent antimicrobial activity in imidazo[1,2-: A] pyridine/pyrimidine-1,2,3-triazoles

Ambien (zolpidem), an imidazo[1,2-a]pyridine derivative, is a commercial drug to treat insomnia which also possesses antitubercular activity against Mycobacterium tuberculosis H37Rv. In this paper, we describe the synthesis of three diverse lead series of imidazo[1,2-a]pyridine/pyrimidine-1,2,3-triazoles (IPTs) which are designed by specific structural modifications of zolpidem. Most of the IPTs exhibited remarkable in vitro antitubercular activity with an MIC of 1.56 μg mL-1, which is two-fold higher than the MIC of zolpidem. Further, the synthesized IPTs displayed moderate inhibitory activity against several bacterial and fungal strains as well, and also showed an acceptable safety profile as verified through in vitro cytotoxicity assessment against Vero cells. In addition, the potent IPTs exhibited promising binding interactions within the active site of the InhA enzyme. An interesting correlation between the in vitro inhibitory activity and the binding mode was observed: most of the potent molecules (MIC = 1.56 μg mL-1) interact through a H-bond with the Tyr 158 residue of the target enzyme. These efforts toward the structural modification of zolpidem could be helpful for further optimization of the IPT core to develop new anti-TB drugs.

KIO4-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach

Herein, we report a KIO4-mediated, sustainable and chemoselective approach for the one-pot C(sp2)?H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.

Exploration of the CuAAC reaction for the synthesis of novel 3-(triazol-1-yl)methyl-imidazo[1,2-a]pyridines

The archetypical CuAAC click chemistry is explored to assemble diverse 3-(triazol-1-yl)methyl-imidazo[1,2-a]pyridines. The approach is simple, general, and environmentally benign to generate a library of novel triazolo-imidazo[1,2- a]pyridine derivatives in good yield (30-90%).