426239-77-2

Basic information

• Product Name: 2-(4-METHOXY-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE
• Synonyms: 2-(4-METHOXY-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE;2-(4-METHOXY-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXALDEHYDE;Albb-006830;2-(4-methoxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde(SALTDATA: FREE);2-(4-methoxyphenyl)-3-imidazo[3,2-a]pyridinecarboxaldehyde;2-(4-methoxyphenyl)imidazo[3,2-a]pyridine-3-carbaldehyde;A3001/0126409;MLS000666576
• CAS NO: 426239-77-2
• Molecular Formula: C₁₅H₁₂N₂O₂
• Molecular Weight: 252.27
• Mol File: 426239-77-2.mol

Chemical Properties

• Appearance: /
• Density: 1.21g/cm³
• Refractive Index: 1.624
• PKA: 4.34±0.50(Predicted)
• CAS DataBase Reference: 2-(4-METHOXY-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXY-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(426239-77-2)
• EPA Substance Registry System: 2-(4-METHOXY-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(426239-77-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 426239-77-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-(4-Methoxy-phenyl)-imidazo[1,2-a]pyridine-3-carbaldehyde is used as a research compound for exploring its potential biological activities and therapeutic effects. Its unique chemical structure and the bioactive properties of imidazo[1,2-a]pyridines make it a promising candidate for the development of new drugs and pharmaceutical agents.
Used in Biochemical Studies:
In the field of biochemistry, 2-(4-Methoxy-phenyl)-imidazo[1,2-a]pyridine-3-carbaldehyde is utilized as a tool compound to study its interactions with various biomolecules and its effects on biological processes. Understanding its biochemical properties can contribute to the discovery of novel mechanisms and potential applications in medicine.
Used in Chemical Synthesis:
2-(4-Methoxy-phenyl)-imidazo[1,2-a]pyridine-3-carbaldehyde can be used as a starting material or intermediate in the synthesis of more complex organic compounds and pharmaceuticals. Its unique structure and functional groups make it a valuable building block for the development of new chemical entities with potential applications in various industries.
Used in Material Science:
Although not explicitly mentioned in the provided materials, the compound's unique structure and properties may also find applications in material science, such as in the development of new materials with specific properties or functions, depending on further research and exploration.

InChI:InChI=1/C15H12N2O2/c1-19-12-7-5-11(6-8-12)15-13(10-18)17-9-3-2-4-14(17)16-15/h2-10H,1H3

Upstream product

• 31562-99-9 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine 
• 504-29-0 2-aminopyridine 
• 1963-36-6 4-methoxycinnamaldehyde 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1312164-39-8 2-(4'-methoxyphenyl)-3-formylimidazo[1,2-a]pyridine thiosemicarbazone 
• 1417910-46-3 3-((4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(4-methoxyphenyl)-1H-imidazo[1,2-a]pyridine 
• 1417910-44-1 2-(4-methoxyphenyl)-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-1H-imidazo[1,2-a]pyridine 
• 1417910-26-9 C₁₅H₁₃N₅O 

Relevant articles and documents

Synthesis, Molecular Docking, BSA, and In Vitro Reactivation Study of Imidazopyridine Oximes Against Paraoxon Inhibited Acetylcholinesterase

Aim: To synthesize and evaluate the fused heterocyclic imidazo[1,2-a]pyridine based oxime as a reactivator against paraoxon inhibited acetylcholinesterase. Background: Organophosphorus compounds (OPs) include parathion, malathion, chlorpyrifos, monocrotop

Design, one-pot green synthesis and antimicrobial evaluation of novel imidazopyridine bearing pyran bis-heterocycles

Herein, we report design, one pot synthesis and antibacterial evaluation of novel imidazopyridine bearing pyran bis-heterocycles. The compounds were synthesized in an aqueous solution of gluconic acid under both conventional heating and ultrasound irradiation. The target compounds were obtained in good to moderate yields with yield of 65–88% in 20–60 min under ultrasonic irradiation. The compounds were characterized by spectroscopic methods IR, 1H NMR, 13C NMR, MS and HRMS. X-ray single crystal structure of 7i was also determined. The compounds were evaluated for antibacterial activity by measuring zone of inhibition using disk diffusion method that revealed that some compounds were inhibiting the growth of Gram +ve and Gram -ve bacteria. Result of minimum inhibitory concentration (MIC) showed that 7a, 7h & 7k from a series 7a-7k inhibited the growth of S. aureus. The minimum bactericidal concentration (MBC) value was determined for 7a, 7h & 7k. MBC/MIC ratio of the derivatives 7a, 7k & 7h suggest former two derivatives act as bactericidal agent & later act as bacteriostatic agents against Gram +ve bacteria. Haemolysis results showed that compounds are non-cytotoxic to erythrocytes.

Copper- A nd DMF-mediated switchable oxidative C-H cyanation and formylation of imidazo[1,2-: A] pyridines using ammonium iodide

The cyanation and formylation of imidazo[1,2-a]pyridines were developed under copper-mediated oxidative conditions using ammonium iodide and DMF as a nontoxic combined cyano-group source and DMF as a formylation reagent. Mechanistic studies indicate that the cyanation of imidazo[1,2-a]pyridines proceeds through a two-step sequence: Initial iodination and then cyanation. The cyanation has a broad substrate scope and high functional group tolerance, and can be safely conducted on a gram scale. A novel copper-mediated formylation using the widely available DMF as the formylation reagent and environmentally friendly molecular oxygen as the oxidant has also been developed. This protocol also provided a convenient approach for the synthesis of clinically used saripidem. This journal is

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.

Novel method for one-step construction of substituted 2-phenylimidazo[1,2-a]pyridine-3-aldehyde by using DMF (N,N-dimethylformamide) as formylation reagent

The invention discloses a novel method for one-step construction of substituted 2-phenylimidazo[1,2-a]pyridine-3-aldehyde by using DMF (N,N-dimethylformamide) as a formylation reagent. According to the method, substituted 2-phenylimidazo[1,2-a]pyridine is

Visible light induced tetramethylethylenediamine assisted formylation of imidazopyridines

A metal-free visible light induced C-3 formylation of imidazo[1,2-a]pyridine has been developed using tetramethylethylenediamine (TMEDA) as a one carbon source. An array of 3-formyl imidazo[1,2-a]pyridines with wide functionality are synthesized using rose bengal as a photosensitizer under ambient air.

Imidazopyridine linked triazoles as tubulin inhibitors, effectively triggering apoptosis in lung cancer cell line

A library of new imidazopyridine linked triazole hybrid conjugates (8a-r) were designed, synthesized and evaluated for their cytotoxicity against four cancer cell lines namely, human lung (A549), human prostate (DU-145), human colon (HCT-116) and breast (

Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis

A metal-free catalytic strategy for the facile synthesis of biologically relevant molecular architectures indolizines and imidazopyridines has been developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael ad

Design, synthesis and biological evaluation of imidazopyridine-propenone conjugates as potent tubulin inhibitors

A library of imidazopyridine-propenone conjugates (8a-8u) were synthesized and evaluated for their antitumor activity against four human cancer cell lines, namely, prostate (DU-145), lung (A549), cervical (Hela) and breast (MCF-7) cancer cell lines. These conjugates showed good to moderate activity against the tested cell lines. Among them, two conjugates (8m and 8q) showed significant antiproliferative activity against the human lung cancer cell line (A549) with IC50 values of 0.86 μM and 0.93 μM, respectively. Flow cytometry analysis revealed that these compounds arrested the cell cycle at the G2/M phase in the human lung cancer cell line (A549), inhibiting tubulin polymerization leading to apoptosis. Further, Hoechst staining, decrease in mitochondrial membrane potential and Annexin V-FITC assay suggested that the cell death was due to apoptosis induction. Overall, the present investigation demonstrated that the synthesized imidazopyridine-propenone conjugates are promising tubulin inhibitors and apoptotic inducers.

CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines

Copper bromide catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes directly led to the formation of 3-formyl-2-phenyl-imidazo[1,2-a]pyridines. The quantum chemical calculations were performed to trace the reaction mechanism and g