1216142-18-5

Usage

General Description

6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylic acid is a chemical compound with the molecular formula C11H10ClN3O2. It is an imidazo[1,2-a]pyridine derivative that contains a chlorine atom and an ethyl group. 6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylic acid is a carboxylic acid, meaning it contains a carboxyl group (COOH) that can act as an acid in chemical reactions. It is commonly used in research and pharmaceutical development, particularly in the study of DNA adduct formation and mutagenesis. Its structure and properties make it a valuable tool for investigating the effects of chemical compounds on genetic material and potential carcinogenicity.

Upstream product

• 1072-98-6 5-chloro-2-pyridylamine 
• 87943-99-5 ethyl 2-bromo-3-oxopentanoate 
• 4949-44-4 ethyl propanoylacetate 
• 1334721-53-7 ethyl 6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylate 

Downstream Products

• 1334717-18-8 N-(([1,1'-biphenyl]-4-yl)methyl)-6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1613627-72-7 N-([1,1'-biphenyl]-4-yl)-6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1613627-74-9 N-([1,1'-biphenyl]-4-ylmethyl)-6-chloro-2-ethyl-N-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1613627-75-0 1-([1,1'-biphenyl]-4-yl)-N-[(6-chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)methyl]methanamine 
• 1613627-79-4 2-([1,1'-biphenyl]-4-yl)-N-(6-chloro-2-ethylimidazo[1,2-a]pyridin-3-yl)acetamide 
• 1334717-20-2 6-chloro-N-{(2'-chloro-[1,1'-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1334717-21-3 6-chloro-N-{(4'-chloro-[1,1'-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1334717-24-6 6-chloro-2-ethyl-N-{(4′-methyl-[1,1′-biphenyl]-4-yl)methyl}-imidazo[1,2-a]pyridine-3-carboxamide 
• 1334717-60-0 6-chloro-N-{(4′-cyano-[1,1′-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1334717-51-9 6-chloro-2-ethyl-N-(4-(4-(4-fluorophenyl)piperazin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide 
• 1334718-23-8 6-chloro-2-ethyl-N-(4-(4-(4-(trifluoromethoxy)phenyl)piperazin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide 
• 1334719-86-6 6-chloro-2-ethyl-N-{4-[4-(4-fluorophenyl)piperidin-1-yl]benzyl}-imidazo[1,2-a]pyridine-3-carboxamide 
• 1334721-16-2 6-chloro-N-(4-(4-(4-chlorophenyl)piperidin-1-yl)benzyl)-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1334718-18-1 6-chloro-2-ethyl-N-(4-(4-(4-(trifluoromethoxy)benzyl)piperazin-1-yl) benzyl)imidazo[1,2-a]pyridine-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and antitubercular evaluation of reduced lipophilic imidazo[1,2-a]pyridine-3-carboxamide derivatives

A series of reduced lipophilic N-benzylic imidazo[1,2-a]pyridine carboxamides (IPAs) with various side chains were designed and synthesized as new anti-TB agents in this work. Five derivatives A2, A3, A4, B1 and B9 exhibit excellent in vitro activity (MIC: 0-∞ and Cmax than Q203 and PBTZ169, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.

Design, synthesis and antimycobacterial activity of less lipophilic Q203 derivatives containing alkaline fused ring moieties

We report herein the design and synthesis of a series of less lipophilic Q203 derivatives containing an alkaline fused ring moiety. Most of them show considerable potency against MTB H37Rv strain (MIC 0.25 μM). Nine compounds (13, 15, 19, 21, 23, 25, 29

N-(2-Phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides containing various amine moieties: Design, synthesis and antitubercular activity

Seven 2,6-disubstituted N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamide series containing various amine moieties were designed and synthesized as new anti-TB agents. Many of them show excellent in vitro activity against both drug-sensitive MTB strain H37Rv and two MDR-MTB clinical isolates (MIC: 0.002–0.030 μg/mL). Compounds 2f, 5e and 5g display acceptable safety and pharmacokinetic profiles, opening a new direction for further development.

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.

Synthesis and structure-activity studies of side chain analogues of the anti-tubercular agent, Q203

The anti-tubercular activity of 6-chloro-2-ethyl-N-(4-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)benzyl)imidazo [1,2-a]pyridine-3-carboxamide (Q203) is modified by varying its side chain. In this study, we synthesized Q203 analogues with different side

Synthesis and structure-activity relationships of novel fused ring analogues of Q203 as antitubercular agents

A set of fused ring analogues of a new antitubercular agent, Q203, was designed and synthesized. To reduce the lipophilicity of Q203 caused by linearly extended side chains, shorter and heteroatoms containing fused rings were introduced into the side chain region. Antitubercular activity was tested against H37Rv-GFP replicating in liquid broth culture medium (extracellular) and within macrophages (intracellular). Many analogues showed potent extracellular activities as well as intracellular activities without cytotoxicity. Among them, compounds 18–21 displayed significant antitubercular activities with favorable metabolic stabilities. Representative compound 21 exhibited excellent in?vivo pharmacokinetic values at high drug exposure levels in the plasma, which makes this compound promising candidate for a new antitubercular drug.

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.