142016-38-4

Basic information

• Product Name: 2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE
• Synonyms: 2-P-TOLYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE;2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE;2-(4-methylphenyl)-3-imidazo[3,2-a]pyridinecarboxaldehyde;2-(4-methylphenyl)imidazo[3,2-a]pyridine-3-carbaldehyde;BAS 11099796;MLS000718352;SMR000290620;ST5290805
• CAS NO: 142016-38-4
• Molecular Formula: C₁₅H₁₂N₂O
• Molecular Weight: 236.27
• Mol File: 142016-38-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(142016-38-4)
• EPA Substance Registry System: 2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(142016-38-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 142016-38-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is used as a synthetic intermediate for the preparation of various organic compounds due to its reactive carbaldehyde group and the presence of the imidazopyridine core.
Used in Medicinal Chemistry:
2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is used as a building block in the design and synthesis of new pharmaceutical agents, potentially targeting a range of therapeutic areas based on its structural features and potential biological activities.
Used in Pharmaceutical Research:
2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is used as a research tool in the discovery and development of novel drugs, where its unique structure may contribute to the creation of new therapeutic agents with improved efficacy and selectivity.
Note: The specific applications and industries for 2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE are not explicitly provided in the materials. The uses listed above are inferred based on the general properties and potential of compounds with similar structures and functional groups in the fields of organic and medicinal chemistry.

Upstream product

• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 65964-60-5 2-para-tolylimidazo[1,2-a]pyridine 
• 504-29-0 2-aminopyridine 
• 56578-35-9 4-methyl-cinnamaldehyde 
• 122-00-9 para-methylacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 619-41-0 4-(bromoacetyl)toluene 

Downstream Products

• 1176040-39-3 (2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanol 
• 1417910-25-8 C₁₅H₁₃N₅ 
• 1417910-41-8 3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-2-p-tolyl-1H-imidazo[1,2-a]pyridine 
• 1417910-43-0 2-p-tolyl-3-((4-p-tolyl-1H-1,2,3-triazol-1-yl)methyl)-1H-imidazo[1,2-a]pyridine 
• 140166-78-5 2-(p-tolyl)imidazole[1,2-a]pyridine-3-carbonitrile 

Relevant articles and documents

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.

Synthesis and biological evaluation of imidazopyridine-oxindole conjugates as microtubule-targeting agents

A library of imidazopyridine-oxindole conjugates was synthesised and investigated for anticancer activity against various human cancer cell lines. Some of the tested compounds, such as 10 a, 10 e, 10 f, and 10 k, exhibited promising antiproliferative activity with GI50 values ranging from 0.17 to 9.31 μM. Flow cytometric analysis showed that MCF-7 cells treated by these compounds arrested in the G2/M phase of the cell cycle in a concentration-dependent manner. More particularly, compound 10 f displayed a remarkable inhibitory effect on tubulin polymerisation. All the compounds depolarised mitochondrial membrane potential and caused apoptosis. These results are further supported by the decreased phosphorylation of Akt at Ser473. Studies on embryonic development revealed that the lead compounds 10 f and 10 k caused delay in the development of zebra fish embryos. Docking of compound 10 f with tubulin protein suggested that the imidazo[1,2-a]pyridine moiety occupies the colchicine binding site of tubulin. Arrested development: A library of imidazopyridine-oxindole conjugates was synthesised and investigated for anticancer activity against various human cancer cell lines. Some of the tested compounds, such as 10 a, 10 e, 10 f, and 10 k, exhibited promising antiproliferative activity. Copyright

Synthesis and antimicrobial activity of novel imidazo[1,2-a]pyridinopyrimidine-2,4,6(1H,3H,5H)-triones and thioxopyrimidine-4,6(1H,5H)diones

A novel series of imidazo[1,2-a]pyridinopyrimidine-2,4,6(1H,3H,5H)-triones and thioxopyrimidine-4,6(1H,5H)diones were synthesized via multistep synthesis starting from 2-aminopyridine on cyclisation with phenacyl bromide followed by Vilsmeier-Haack and Kn

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, synthesis, and biological evaluation of chalcone-linked thiazole-imidazopyridine derivatives as anticancer agents

A novel library of chalcone linked thiazole-imidazopyridine (12a–j) derivatives were designed, synthesized, and their structures were characterized by 1H NMR, 13C NMR and mass spectral studies. Further, all compounds were tested for their anticancer effects on four human cancer cell lines including MCF-7 (breast carcinoma), A549 (lung carcinoma), DU-145 (prostate carcinoma) and MDA MB-231 (breast carcinoma) by employing MTT method, using etoposide as the positive control. Among them, compound 12b displayed more potent anticancer activity against four cancer cell lines when compared to the positive control.

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

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

2-PHENYL-3-(PIPERAZINOMETHYL)IMIDAZO[1,2-A]PYRIDINE DERIVATIVES AS BLOCKERS OF TASK-1 AND TASK-2 CHANNELS, FOR THE TREATMENT OF SLEEP-RELATED BREATHING DISORDERS

The present application relates to novel 2-phenyl-3-(piperazinomethyl)imidazo[1,2-a]pyridine derivatives, to processes for their preparation, to their use alone or in combinations for the treatment and/or prevention of diseases, and to their use for prepa

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.

SUBSTITUTED PERHYDROPYRROLO[3,4-C]PYRROLE DERIVATIVES AND THE USE OF SAME

The present application relates to novel (2-phenylimidazo[1,2-a]pyridin-3-yl)methyl-substituted perhydropyrrolo[3,4-c]pyrrole derivatives, to methods for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention