61985-32-8

Basic information

• Product Name: (imidazol-4-yl)(phenyl)methanone
• Synonyms: (imidazol-4-yl)(phenyl)methanone
• CAS NO: 61985-32-8
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18332
• Mol File: 61985-32-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (imidazol-4-yl)(phenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (imidazol-4-yl)(phenyl)methanone(61985-32-8)
• EPA Substance Registry System: (imidazol-4-yl)(phenyl)methanone(61985-32-8)

Safety Data

• Hazardous Substances Data: 61985-32-8(Hazardous Substances Data)

Usage

Description

(imidazol-4-yl)(phenyl)methanone, also known as 4-(4-imidazol-1-ylphenyl)butan-2-one, is a compound with the molecular formula C12H12N2O. It is a ketone derivative featuring a phenyl and imidazol-4-yl group attached to the carbon atom. This chemical has potential pharmaceutical applications and is widely utilized in the synthesis of various pharmaceuticals and organic building blocks. It also plays a significant role in the study of structure-activity relationships in drug discovery and development. Furthermore, (imidazol-4-yl)(phenyl)methanone has been investigated for its potential anticonvulsant and neuroprotective properties.

Uses

Used in Pharmaceutical Synthesis:
(imidazol-4-yl)(phenyl)methanone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex molecular structures, contributing to the development of new drugs with improved efficacy and safety profiles.
Used in Drug Discovery and Development:
In the field of drug discovery and development, (imidazol-4-yl)(phenyl)methanone is used as a structural component to study structure-activity relationships. This helps researchers understand how the structure of a compound influences its biological activity, leading to the design of more effective and targeted therapeutic agents.
Used in Neurological Applications:
(imidazol-4-yl)(phenyl)methanone is used as a potential therapeutic agent in neurological applications due to its investigational anticonvulsant and neuroprotective properties. These properties make it a promising candidate for the treatment of conditions such as epilepsy and other neurological disorders where seizure control and neuroprotection are critical.
Used in Organic Chemistry:
In the realm of organic chemistry, (imidazol-4-yl)(phenyl)methanone is used as a versatile building block for the creation of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a valuable tool for the synthesis of complex organic molecules with diverse applications.

Upstream product

• 133228-20-3 5-hydroxydiphenylmethyl-N,N-dimethylimidazole-1-sulphonamide 
• 133228-19-0 1-(Dimethylsulfamoyl)-5-imidazol 
• 288-32-4 1H-imidazole 
• 98-88-4 benzoyl chloride 
• 2302-25-2 4-bromo-1 H-imidazole 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases

Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption, distribution, metabolism, and excretion (ADME) predictions were performed. The synthesized core skeleton was bound to important regions of the active site of AChE such as the peripheral anionic site (PAS), oxyanion hole (OH), and anionic subsite (AS). Selectivity of the reported test compounds was calculated and enzyme kinetic studies revealed that they behave as competitive inhibitors, while two of the test compounds showed noncompetitive inhibitory behavior. ADME predictions revealed that the synthesized molecules might pass through the blood brain barrier and intestinal epithelial barrier and circulate freely in the blood stream without binding to human serum albumin. While the toxicity of one compound on the WS1 (skin fibroblast) cell line was 1790 μM, its toxicity on the SH-SY5Y (neuroblastoma) cell line was 950 μM.

Synthesis of novel imidazopyridines and their biological evaluation as potent anticancer agents: A promising candidate for glioblastoma

Novel imidazopyridine derivatives were synthesized according to a very simple protocol and then subjected to cytotoxicity testing against LN-405 cells. Two of the compounds exhibited antiproliferative effects on LN-405 cells at 10 and 75 μM and were selected as lead compounds for further study. Safety experiment for lead compounds on WS1 was carried out and IC50 values were calculated as 480 and 844 μM. LN-405 cell line were incubated with the lead compounds and then tested for DNA damage by comet assay and effects on cell cycle using flow cytometry. The results of these two tests showed that both lead compounds affected the G0/G1 phase and did not allow the cells to reach the synthesis phase. The log BB (blood–brain barrier) and Caco-2 permeability of the synthesized molecules were calculated and it was shown that imidazopyridine derivatives taken orally are likely to pass through gastrointestinal membrane and the blood–brain barrier.

Carbodesilylation of (Trimethylsilyl)imidazoles and -pyrazoles

The preparation of the 1-methyl(trimethylsilyl) (TMS)-substituted imidazoles 3a, 4a, 8, 9, and 11a by silylation of the corresponding metallated imidazoles is described.Carbodesilylation of 3 with aldehydes or carboxylic halogenides occurs selectively in 2-position.In the presence of a strong base (CsF) the reactivity against carbon electrophiles correlates well with the stability of the imidazolyl anions; regioselective carbodesilylation in 2-, 5-, or 4-position of the twofold TMS-substituted imidazoles 3a and 9 therefore is possible, which allows the synthesis of a great variety of hydroxyalkyl-substituted imidazoles and of acylimidazoles.By using the dimethylsulfamoyl substituent as an N-protecting group, the N-unsubstituted 5-benzoylimidazole (26) as well as the comparable 5-benzoyl-pyrazole (30b) and 5-(hydroxyphenylmethyl)pyrazole (30a) are accessible. Key Words : Imidazoles, (trimethylsilyl)-, carbodesilylation of / Pyrazoles, (trimethylsilyl)-, carbodesilylation of / Carbodesilylation