81448-48-8

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
ETHYL 2,7-DIMETHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE is used as a research compound for its potential biological activities. It is particularly valuable in the discovery and development of new drugs due to its ability to modulate specific biological processes, which can be critical in treating various diseases and conditions.
Used in Organic Synthesis:
In the field of organic synthesis, ETHYL 2,7-DIMETHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE serves as a key intermediate or building block in the synthesis of more complex organic molecules. Its unique structure and functional groups make it a versatile component in creating a wide range of chemical products.
Used in Medicinal Chemistry:
ETHYL 2,7-DIMETHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE is utilized in medicinal chemistry as a starting material or a modifying agent to create new pharmaceutical agents. Its structural features allow for the development of compounds with specific therapeutic properties, contributing to the advancement of medicine and healthcare.
Used in Chemical Education and Training:
ETHYL 2,7-DIMETHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE can also be used in educational settings for teaching purposes, particularly in courses related to organic chemistry, medicinal chemistry, and pharmaceutical sciences. It provides students with hands-on experience in handling and synthesizing complex organic molecules, fostering a deeper understanding of chemical reactions and processes.

InChI:InChI:1S/C12H14N2O2/c1-4-16-12(15)11-9(3)13-10-7-8(2)5-6-14(10)11/h5-7H,4H2,1-3H3

Upstream product

• 695-34-1 2-Amino-4-methylpyridine 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 64-17-5 ethanol 
• 105-39-5 chloroacetic acid ethyl ester 
• 84911-18-2 ethyl 2-bromoacetoacetate 

Downstream Products

• 1282522-64-8 N-benzyl-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-65-9 N-(2-methoxybenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-66-0 N-(3-methoxybenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-67-1 N-(4-methoxybenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-68-2 N-(4-methylbenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-69-3 N-(4-chlorobenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-70-6 N-(3,4-dichlorobenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-71-7 N-(3-fluorobenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1282522-72-8 N-(phenyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1300029-80-4 N-(3-methoxyphenyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1300031-15-5 2,7-dimethyl-N-(4-(4-(trifluoromethyl)phenoxy)phenyl)imidazo[1,2-a]pyridine-3-carboxamide 
• 1300031-03-1 N-(4-(4-Chlorophenoxy)benzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1300031-02-0 N-(4-(4-fluorophenoxy)benzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1300030-62-9 2,7-dimethyl-N-(4-sulfamoylbenzyl)imidazo[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 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.

BENZYL AMINE-CONTAINING HETEROCYCLIC COMPOUNDS AND COMPOSITIONS USEFUL AGAINST MYCOBACTERIAL INFECTION

Described herein are compounds and compositions, and methods of making and their use as effective agents against mycobacterial infections.

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives

We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.

Identification of N-(2-Phenoxyethyl)imidazo[1,2-a]pyridine-3-carboxamides as New Antituberculosis Agents

A series of imidazo[1,2-a]pyridine carboxamides (IPAs) bearing an N-(2-phenoxyethyl) moiety was designed and synthesized as new antitubercular agents. Seven 2,6-dimethyl IPAs demonstrated excellent in vitro activity (MIC: 0.025-0.054 μg/mL) against the drug susceptive H37Rv strain and two clinically isolated multidrug-resistant Mycobacterium tuberculosisstrains. Compound 10j displayed acceptable safety and pharmacokinetic properties, opening a new direction for further development.

Design, syntheses, and anti-tuberculosis activities of conjugates of piperazino-1,3-benzothiazin-4-ones (pBTZs) with 2,7-dimethylimidazo [1,2-a]pyridine-3-carboxylic acids and 7-phenylacetyl cephalosporins

Tuberculosis (TB) remains one of the most threatening diseases in the world and the need for development of new therapies is dire. Herein we describe the rationale for the design and subsequent syntheses and studies of conjugates between pBTZ and both the imidazopyridine and cephalosporin scaffolds. Overall some compounds exhibited notable anti-TB activity in the range of 2-0.2 μM in the Microplate Alamar Blue (MABA) Assay.

Microwave assisted synthesis of disubstituted imidazo[1,2-a]pyridine-3-carboxylic acid esters

A novel and efficient synthetic method leveraging microwave-assisted organic synthesis (MAOS) to prepare disubstituted imidazo[1,2-a]- pyridine-3-carboxylic acid esters (IPCEs) (3a-z), the key intermediates for a class of novel anti-tuberculosis agents, is reported. Under microwave heating at 120 °C for 20 or 30 min, the condensations of 2-aminopyridines (1a-k) and ethyl 2-halogenated acetoacetates (2a-d) were conveniently performed in ethanol with acceptable yields.

Scaffold-switching: An exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine- 3-carboxylates

A set of 5,6-fused bicyclic heteroaromatic scaffolds were investigated for their in vitro anti-tubercular activity versus replicating and non-replicating strains of Mycobacterium tuberculosis (Mtb) in an attempt to find an alternative scaffold to the imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidines that were previously shown to have potent activity against replicating and drug resistant Mtb. The five new bicyclic heteroaromatic scaffolds explored in this study include a 2,6-dimethylimidazo[1,2-b]pyridazine-3-carboxamide (7), a 2,6-dimethyl-1H-indole-3-carboxamide (8), a 6-methyl-1H-indazole-3-carboxamide (9), a 7-methyl-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide (10), and a 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxamide (11). Additionally, imidazo[1,2-a]pyridines isomers (2 and 12) and a homologous imidazo[1,2-a] pyrimidine isomer (6) were prepared and compared. Compounds 2 and 6 were found to be the most potent against H37Rv Mtb (MIC's of 0.1 μM and 1.3 μM) and were inactive (MIC >128 μM) against Staphylococcus aureus, Escherichia coli and Candida albicans. Against other non-tubercular mycobacteria strains, compounds 2 and 6 had activity against Mycobacterium avium (16 and 122 μM, respectively), Mycobacterium kansasii (4 and 19 μM, respectively), Mycobacterium bovis BCG (1 and 8 μM, respectively) while all the other scaffolds were inactive (>128 μM).

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.