138642-96-3

Usage

Uses

Used in Pharmaceutical Research:
6-CHLORO-2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID is used as a precursor in the synthesis of new drugs, contributing to the development of pharmaceuticals with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 6-CHLORO-2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID is employed as an intermediate, facilitating the production of other heterocyclic compounds that may have various applications in different industries.
Used in Antimicrobial and Antifungal Applications:
6-CHLORO-2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID is studied for its potential antimicrobial and antifungal properties, making it a target for further investigation in the development of new medical treatments to combat resistant infections.
Used in the Development of New Medical Treatments:
Due to its potential biological activity, 6-CHLORO-2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID is used in research aimed at developing new medical treatments, particularly those targeting microbial and fungal infections.

Upstream product

• 330858-13-4 ethyl 6-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylate 
• 1072-98-6 5-chloro-2-pyridylamine 

Downstream Products

• 1296202-56-6 7-chloro-N-(3-methoxybenzyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1440650-53-2 7-chloro-N-(4-(4-fluorophenoxy)benzyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1334716-80-1 N-([1,1'-biphenyl]-4-ylmethyl)-6-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 1,2,3-triazole analogues of Imidazo-[1,2-a]-pyridine-3-carboxamide against Mycobacterium tuberculosis

Twenty-eight novel 1,2,3-triazole analogues of imidazo-[1,2-a]-pyridine-3-carboxamide were designed and synthesized based on hybridization approach. The structure of the final compounds are characterized using 1HNMR, 13CNMR, LCMS and

Synthesis, study of antileishmanial and antitrypanosomal activity of imidazo pyridine fused triazole analogues

Four groups, thirty-five compounds in total, of novel 1,2,3-triazole analogues of imidazo-[1,2-a]-pyridine-3-carboxamides were designed and synthesized using substituted pyridine, propargyl bromide, 2-azidoethyl 4-methyl benzenesulfonate and substituted acetylenes. These compounds were characterized using 1H NMR, 13C NMR, LCMS and elemental analyses and a crystal structure was obtained for one of the significantly active compounds, 8f. All the synthesized and characterized compounds were screened in vitro for antileishmanial and antitrypanosomal activity against Leishmania major and Trypanosoma brucei parasites, respectively. Among the tested analogues, fivecompounds (8d, 8f, 8j, 10b and 10d) exhibited significant antileishmanial activity while three compounds (10b, 11a and 11b) showed substantial activity against T. brucei parasite. In silico ADME prediction studies depicted that the essential compounds obeyed Lipinski's rule of five. The predictedin silico toxicity profile suggested that the tested compounds would be non-toxic, which was confirmed experimentally by the lack of cytotoxicity against HeLa cells. Finally, a molecular docking study was also performed, for 10d the most active antileishmanial compound, to study its putative binding pattern at the active site of the selected leishmanial trypanothione reductase target.

Design, synthesis, and biological evaluation of novel imidazo[1,2-a]pyridinecarboxamides as potent anti-tuberculosis agents

Tuberculosis (TB) is a highly infectious disease that has been plaguing the human race for centuries. The emergence of multidrug-resistant strains of TB has been detrimental to the fight against tuberculosis with very few safe therapeutic options availabl

Design, synthesis and biological activity of N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides as new antitubercular agents

A series of N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides (IPAs), based on the structure of WZY02 discovered in our lab, were designed and synthesized as new anti-TB agents. Results reveal that many of them exhibit excellent in vitro inhibitory activity with low nanomolar MIC values against both drug-sensitive MTB strain H37Rv and drug-resistant clinical isolates. Compounds 15b and 15d display good safety and pharmacokinetic profiles, suggesting their promising potential to be lead compounds for future antitubercular drug discovery.

Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug- resistant anti-tuberculosis agent

A critical unmet clinical need to combat the global tuberculosis epidemic is the development of potent agents capable of reducing the time of multi-drug-resistant (MDR) and extensively-drug-resistant (XDR) tuberculosis therapy. In this paper, we report on the optimization of imidazo[1,2-a]pyridine amide (IPA) lead compound 1, which led to the design and synthesis of Q203 (50). We found that the amide linker with IPA core is very important for activity against Mycobacterium tuberculosis H37Rv. Linearity and lipophilicity of the amine part in the IPA series play a critical role in improving in vitro and in vivo efficacy and pharmacokinetic profile. The optimized IPAs 49 and 50 showed not only excellent oral bioavailability (80.2% and 90.7%, respectively) with high exposure of the area under curve (AUC) but also displayed significant colony-forming unit (CFU) reduction (1.52 and 3.13 log10 reduction at 10 mg/kg dosing level, respectively) in mouse lung.

Advancement of imidazo[1,2-a]pyridines with improved pharmacokinetics and nM activity vs. Mycobacterium tuberculosis

A set of 14 imidazo[1,2-a]pyridine-3-carboxamides was synthesized and screened against Mycobacterium tuberculosis H37Rv. The minimum inhibitory concentrations of 12 of these agents were ≤1 μM against replicating bacteria and 5 compounds (9, 12, 16, 17, and 18) had MIC values ≤0.006 μM. Compounds 13 and 18 were screened against a panel of MDR and XDR drug resistant clinical Mtb strains with the potency of 18 surpassing that of clinical candidate PA-824 by nearly 10-fold. The in vivo pharmacokinetics of compounds 13 and 18 were evaluated in male mice by oral (PO) and intravenous (IV) routes. These results indicate that readily synthesized imidazo[1,2-a]pyridine-3-carboxamides are an exciting new class of potent, selective anti-TB agents that merit additional development opportunities.