21801-79-6

Usage

Chemical Properties

Pink solid

InChI:InChI=1/C9H8N2O2/c1-6-8(9(12)13)11-5-3-2-4-7(11)10-6/h2-5H,1H3,(H,12,13)

Upstream product

• 95607-07-1 3-bromo-2-methyl-pyrido[1,2-a]pyrimidin-4-one 
• 2549-19-1 ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate 
• 504-29-0 2-aminopyridine 
• 943112-78-5 methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 1693-94-3 2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 

Downstream Products

• 21801-89-8 2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1333519-53-1 N-benzyl-N-methyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 478245-46-4 (2-methylimidazo[1,2-a]pyridin-3-yl)(4-morpholino)methanone 
• 135854-51-2 2-methylimidazo[1,2-a]pyridine-3-carbonyl chloride 
• 570361-36-3 (2-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone 
• 352024-12-5 N-benzyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1367714-25-7 C₂₁H₂₂F₂N₄O 
• 1396397-27-5 C₁₉H₂₀N₄O₃ 
• 1093255-52-7 N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide trifluoroacetate 
• 1334716-55-0 N-([1,1'-biphenyl]-4-ylmethyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 903744-27-4 2-methyl-N-phenethylimidazo[1,2-a]pyridine-3-carboxamide 
• 329715-90-4 N-cyclohexyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 357160-94-2 N-(4-bromophenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 477852-38-3 N-(4-chlorophenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 

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.

Identification and development of 2-methylimidazo[1,2-a]pyridine-3- carboxamides as Mycobacterium tuberculosis pantothenate synthetase inhibitors

In the present study, we used crystal structure of mycobacterial pantothenate synthetase (PS) bound with 2-(2-(benzofuran-2-ylsulfonylcarbamoyl)- 5-methoxy-1H-indol-1-yl) acetic acid inhibitor for virtual screening of antitubercular compound database to identify new scaffolds. One of the identified lead was modified synthetically to obtain thirty novel analogues. These synthesized compounds were evaluated for Mycobacterium tuberculosis (MTB) PS inhibition study, in vitro antimycobacterial activities and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, N′-(1-naphthoyl)- 2-methylimidazo[1,2-a]pyridine-3-carbohydrazide (5b) was found to be the most active compound with IC50 of 1.90 ± 0.12 μM against MTB PS, MIC of 4.53 μM against MTB with no cytotoxicity at 50 μM. The binding affinity of the most potent inhibitor 5b was further confirmed biophysically through differential scanning fluorimetry.

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.

Design, synthesis, and pharmacological evaluation of N-acylhydrazones and novel conformationally constrained compounds as selective and potent orally active phosphodiesterase-4 inhibitors

Among a small series of tested N-acylhydrazones (NAHs), the compound 8a was selected as a selective submicromolar phosphodiesterase-4 (PDE4) inhibitor associated with anti-TNF-α properties measured both in vitro and in vivo. The recognition pattern of compound 8a was elucidated through molecular modeling studies based on the knowledge of the 3D-structure of zardaverine, a PDE4 inhibitor resembling the structure of 8a, cocrystallized with the PDE4. Based on further conformational analysis dealing with N-methyl-NAHs, a quinazoline derivative (19) was designed as a conformationally constrained NAH analogue and showed similar in vitro pharmacological profile, compared with 8a. In addition 19 was found active when tested orally in LPS-evoked airway hyperreactivity and fully confirmed the working hypothesis supporting this work.

Identification of fused bicyclic heterocycles as potent and selective 5-HT2A receptor antagonists for the treatment of insomnia

A series of fused bicyclic heterocycles was identified as potent and selective 5-HT2A receptor antagonists. Optimization of the series resulted in compounds that had improved PK properties, favorable CNS partitioning, good pharmacokinetic properties, and significant improvements on deep sleep (delta power) and sleep consolidation.

ANTI-INFECTIVE COMPOUNDS

The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

Synthesis and characterisation of novel N substituted 2-methylimidazo[1,2a] pyridine-3-carboxamides

A series of novel N substituted 2-methylimidazo[1,2a]pyridine-3- carboxamides has been synthesised in high yield by a convenient method and characterised by 1H NMR, MS, IR and elemental analysis.

HETEROARYLS AND THEIR USE AS PI3K INHIBITORS

This invention provides compounds of formula (IA) or (IB): wherein R1, R2, G1 and HY are as described in the specification. The compounds are inhibitors of PI3K and/or mTor and are thus useful for treating proliferative, inflammatory, or cardiovascular disorders.