330858-13-4

Basic information

• Product Name: 6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: BUTTPARK 13\05-81;ETHYL 6-CHLORO-2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE;6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;ethyl 6-chloro-2-methylH-imidazo[1,2-a]pyridine-3-carboxylate;ethyl 6-chloro-2-methy-imidazo[1,2-a]pyridine-3-carboxylate
• CAS NO: 330858-13-4
• Molecular Formula: C11H11ClN2O2
• Molecular Weight: 238.67
• Mol File: 330858-13-4.mol

Chemical Properties

• Appearance: /
• Density: 1.32g/cm³
• Refractive Index: 1.602
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(330858-13-4)
• EPA Substance Registry System: 6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(330858-13-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 330858-13-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER is used as a building block for the synthesis of various drug molecules, leveraging its chemical structure to create new therapeutic agents.
Used in Biological Research:
In biological research, 6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER is used as an enzyme and receptor inhibitor, contributing to the study of biological pathways and the development of targeted therapies.
Used in Agrochemicals:
6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER may have applications in the agrochemical industry, potentially serving as a component in the development of pesticides or other agricultural chemicals, although specific uses are not detailed in the provided materials.
Used in Materials Science:
6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER may also find utility in materials science, possibly due to its structural properties that could be exploited in the creation of new materials or the modification of existing ones, although the exact applications in this field are not specified in the provided information.

InChI:InChI=1/C11H11ClN2O2/c1-3-16-11(15)10-7(2)13-9-5-4-8(12)6-14(9)10/h4-6H,3H2,1-2H3

Upstream product

• 1072-98-6 5-chloro-2-pyridylamine 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 141-97-9 ethyl acetoacetate 
• 84911-18-2 ethyl 2-bromoacetoacetate 

Downstream Products

• 1296202-56-6 7-chloro-N-(3-methoxybenzyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 138642-96-3 6-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid 
• 1334716-80-1 N-([1,1'-biphenyl]-4-ylmethyl)-6-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxamide 

Relevant articles and documents

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

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

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.

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.

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.