325736-91-2

Basic information

• Product Name: 2-(4-methoxyphenyl)-6-chloroimidazo[1,2-a]pyridine
• Synonyms: 2-(4-methoxyphenyl)-6-chloroimidazo[1,2-a]pyridine
• CAS NO: 325736-91-2
• Molecular Formula: C₁₄H₁₁ClN₂O
• Molecular Weight: 259
• Mol File: 325736-91-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-methoxyphenyl)-6-chloroimidazo[1,2-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methoxyphenyl)-6-chloroimidazo[1,2-a]pyridine(325736-91-2)
• EPA Substance Registry System: 2-(4-methoxyphenyl)-6-chloroimidazo[1,2-a]pyridine(325736-91-2)

Safety Data

• Hazardous Substances Data: 325736-91-2(Hazardous Substances Data)

Usage

Chemical Class

The compound belongs to the imidazopyridine class.

Structure

It is a heterocyclic compound with an imidazo[1,2-a]pyridine core structure.

Substituents

The compound contains a 4-methoxyphenyl and a 6-chloro substituent.

Pharmaceutical Applications

2-(4-methoxyphenyl)-6-chloroimidazo[1,2-a]pyridine has potential pharmaceutical applications.

Biological Activities

It has been investigated for its biological activities, including its potential as an antitumor agent.

Medicinal Chemistry

The compound may have potential use in medicinal chemistry for the development of new drugs targeting a range of medical conditions.

Further Research

Further research and investigation are necessary to fully understand and utilize the properties and potential applications of this chemical compound.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 1072-98-6 5-chloro-2-pyridylamine 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 93435-57-5 α-tosyloxy-p-methoxyacetophenone 
• 54187-96-1 1-(chloromethyl)-1H-benzotriazole 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 

Downstream Products

• 365213-36-1 1-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine 
• 365213-55-4 2-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetamide 
• 365213-64-5 [6-chloro-2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridin-3-yl]-acetic acid 

Relevant articles and documents

Synthesis, biological evaluation and molecular modeling studies of imidazo[1,2-a]pyridines derivatives as protein kinase inhibitors

We report here the synthesis, the biological evaluation and the molecular modeling studies of new imidazo[1,2-a]pyridines derivatives designed as potent kinase inhibitors. This collection was obtained from 2-aminopyridines and 2-bromoacetophenone which af

Design, Synthesis, and Biological Evaluation of Novel Fluorescent Probes Targeting the 18-kDa Translocator Protein

A series of fluorescent probes from the 6-chloro-2-phenylimidazo[1,2-a]pyridine-3-yl acetamides ligands featuring the 7-nitro-2-oxa-1,3-diazol-4-yl (NBD) moiety has been synthesized and biologically evaluated for their fluorescence properties and for thei

A simple and efficient route to 2-arylimidazo[1,2-a]pyridines and zolimidine using automated grindstone chemistry

A green and efficient mechanochemical method for the synthesis of a series of 2-arylimidazo[1,2-a]pyridines was developed using an electrical grinder. I2 catalyzed mechanochemical grinding facilitates the cyclocondensation reaction between various aryl methyl ketones and 2-aminopyridines to afford 2-arylimidazo[1,2-a]pyridines in good yields at ambient temperature. The method was successfully used for the gram-scale synthesis of a marketed drug, zolimidine. The noticeable advantages of this environmentally sustainable protocol include mild conditions, simple instrumentation, inexpensive catalyst, atom economy, short reaction time etc.

Efficient and green microwave-assisted one-pot synthesis of azaindolizines in PEG-400 and water

A facile, convenient, environmentally benign, and one-pot synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines and in-situ generated phenacyl bromides under microwave irradiation in polyethylene glycol (PEG-400) and water (1:2) has been developed. The protocol provides a better alternative to the existing method as it involves utilization of in-situ-generated α-bromoacetophenones, avoids the use of lachrymatric α-haloketones as well as volatile toxic organic solvents, and reduces the reaction time to obtain excellent yield.

One-pot synthesis of 2-phenylimidazo[1,2-α]pyridines from acetophenone, [Bmim]Br3 and 2-aminopyridine under solvent-free conditions

One-pot synthesis of 2-phenylimidazo[1,2-α]pyridines from acetophenone, [Bmim]Br3 and 2-aminopyridine under solvent-free conditions in the presence of Na2CO3, gave the corresponding 2-phenylimidazo[1,2-α]pyridines in excel

Iodobenzene-catalyzed synthesis of imidazo[1,2-a]pyridines from aryl ketones with mCPBA in ionic liquid

Iodobenzene-catalyzed synthesis of imidazo[1,2-a]pyridines from aryl ketones with mCPBA as a cooxidant in ionic liquid is described. The method is simple, rapid and practical, generating Imidazo[1,2-a]pyridines from the aryl ketone without isolation of α-

Synthesis and biological evaluation of substituted [18F] imidazo[1,2-a]pyridines and [18F]pyrazolo[1,5-a]pyrimidines for the study of the peripheral benzodiazepine receptor using positron emission tomography

The fluoroethoxy and fluoropropoxy substituted 2-(6-chloro-2-phenyl) imidazo[1,2-a]pyridin-3-yl)-N,N-diethylacetamides 8 (PBR102) and 12 (PBR111) and 2-phenyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamides 15 (PBR099) and 18 (PBR146) wer

Synthesis of bridgehead nitrogen heterocycles on a solid surface

Bridgehead nitrogen heterocycles were synthesized from heteroaromatic amidines and cyclic or acyclic α-bromoketones under solvent-free conditions at room temperature on a solid surface in excellent yields, which are higher than those obtained with hithert

Hypervalent iodine(III) sulfonate mediated synthesis of imidazo[1,2-a]pyridines

A direct and efficient method for the conversion of alkyl aryl ketones to imidazo[1,2-a]pyridines has been developed based on initial formation of α-organosulfonyloxy ketones and their subsequent cyclocondensation by 2-aminopyridines in one-pot conditions

A structure-activity relationship study of the affinity of selected imidazo[1,2-a]pyridine derivatives, congeners of zolpidem, for the ω1-subtype of the benzodiazepine receptor

A series of 6-substituted 2-aryl-N,N-dimethylimidazol [1,2-a]pyridine-3-acetamides, congeners of zolpidem and alpidem, was synthesized and tested in vitro for binding with the benzodiazepine receptor in the competition with 3H-zolpidem as an ω1-selective radioligand. Molecular electrostatic potential (MEP) and the HOMO and LUMO energies were calculated for the compounds by semi-empirical quantum chemistry methods. The lipophilicity parameter of the compounds, expressed as the logarithm of the octanol-water partition coefficient (log P), was calculated; alternatively, standard values of the Hansch hydrophobic substituent constants π were used. In agreement with earlier investigations on the benzodiazepine receptor ligands with a high preference for the ω1-subtype, a quantitative correlation of the biological data with molecular parameters has revealed a significant dependence (r=0.954) of the binding affinity (IC50) on the deepest MEP minimum, in this case associated with the amide carbonyl oxygen atom. The lipophilicity parameters were found to be of lower significance.