24155-47-3

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Phenyl-2-(1-imidazolyl)ethanol is used as a key building block for the synthesis of various pharmaceuticals and biologically active compounds. Its unique structure allows it to be a versatile component in the development of new drugs.
Used in Antifungal Applications:
1-Phenyl-2-(1-imidazolyl)ethanol is used as an antifungal agent due to its ability to inhibit the growth of fungi. This property makes it a useful intermediate in the development of new antifungal drugs.
Used in Antibacterial Applications:
Similarly, 1-Phenyl-2-(1-imidazolyl)ethanol is used as an antibacterial agent, exhibiting properties that help control bacterial growth. This characteristic is beneficial in the creation of new antibiotics and related treatments.
Used in Medicinal Chemistry:
Due to its unique chemical structure and pharmacological properties, 1-Phenyl-2-(1-imidazolyl)ethanol has potential applications in the field of medicine. It can be utilized in the design and synthesis of novel therapeutic agents.
Used in Biochemical Research:
1-Phenyl-2-(1-imidazolyl)ethanol also has potential uses in biochemical research, where it can be employed to study various biological processes and interactions, contributing to a better understanding of its effects and potential applications in medicine and drug development.

InChI:InChI=1/C11H12N2O/c14-11(8-13-7-6-12-9-13)10-4-2-1-3-5-10/h1-7,9,11,14H,8H2

Upstream product

• 24155-34-8 2-(1H-imidazol-1-yl)-1-phenylethanone 
• 288-32-4 1H-imidazole 
• 96-09-3 styrene oxide 
• 70-11-1 α-bromoacetophenone 
• 122-60-1 Phenyl glycidyl ether 
• 98-86-2 acetophenone 
• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 
• 7568-93-6 2-Amino-1-phenylethanol 

Downstream Products

• 133993-29-0 ethyl 7-phenyl-8-(1-imidazolyl)-6-oxaoctanoate 
• 127847-26-1 Hexanedioic acid benzyl ester 2-imidazol-1-yl-1-phenyl-ethyl ester 
• 1208245-70-8 1-[2-(2-fluoro-4-nitro-phenoxy)-2-phenyl-ethyl]-1H-imidazole 
• 1208245-71-9 1-[2-(2-nitro-phenoxy)-2-phenyl-ethyl]-1H-imidazole 
• 1208245-69-5 1-[2-(4-nitro-phenoxy)-2-phenyl-ethyl]-1H-imidazole 
• 1208245-68-4 1-[2-phenyl-2-(4-trifluoromethyl-phenoxy)-ethyl]-1H-imidazole 

Relevant academic research and scientific papers

N-Functionalised heterocyclic dicarbene complexes of silver: Synthesis and structural studies

A range of new diimidazolium salts, held together by an alkyl unit and bearing alcohol pendant arms on their nitrogen, was synthesized. A short modular reaction pathway leads to the N-heterocyclic carbene (NHC) precursors, differing by the flexibility of

Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes

The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.

Design, synthesis and biological evaluation of imidazole and triazole-based carbamates as novel aromatase inhibitors

In the search for novel aromatase inhibitors, a series of triazole and imidazole-based carbamate derivatives were designed and synthesized. Final compounds were thus evaluated against human aromatase by in vitro kinetic experiments in a fluorimetric assay in comparison with letrozole. The effect of most active derivatives 13a and 15c was then evaluated in vitro on the human breast cancer cell line MCF7 by MTT assay, cytotoxicity assay (LDH release) and cell cycle analysis, revealing a dose-dependent inhibition profile of cell viability and low micromolar IC50 values. In addition, docking simulations were also carried out to elucidate at a molecular level of detail the binding modes adopted to target human aromatase.

Synthesis, in vitro antifungal evaluation and docking studies of novel derivatives of imidazoles and benzimidazoles

A series of imidazole and benzimidazole derivatives was designed and prepared in good yields via convenient and efficient two steps synthetic route using readily available starting materials. The structures of the synthesized compounds and their intermedi

Diaryl-containing imidazole compound and preparation method and medical application thereof

The invention discloses a diaryl-containing imidazole compound. The invention further discloses application of the diaryl-containing imidazole compound to preparation of drugs for preventing or treating Alzheimer's disease. The inventor screens butyrylcholine esterase and IDO1 as carriers for inhibiting the activity to evaluate the effect of the diaryl imidazole compound to treat Alzheimer's disease, and finds that the diaryl imidazole compound has good in vitro activity, and can be further developed as a precursor substance for performing the Alzheimer's disease resistant effect by inhibitingthe activity of cholinesterase. (The formula is shown in the description).

New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies

Azole antifungals are potent inhibitors of fungal lanosterol 14α demethylase (CYP51) and have been used for eradication of systemic candidiasis clinically. Herein we report the design, synthesis, and biological evaluation of a series of 1-phenyl/1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethanol esters. Many of these derivatives showed fungal growth inhibition at very low concentrations. Minimal inhibition concentration (MIC) value of 15 was 0.125?μg/mL against Candida albicans. Additionally, some of our compounds, such as 19 (MIC: 0.25?μg/mL), were potent against resistant C.?glabrata, a fungal strain less susceptible to some first-line antifungal drugs. We confirmed their antifungal efficacy by antibiofilm test and their safety against human monocytes by cytotoxicity assay. To rationalize their mechanism of action, we performed computational analysis utilizing molecular docking and dynamics simulations on the C.?albicans and C.?glabrata CYP51 (CACYP51 and CGCYP51) homology models we built. Leu130 and T131 emerged as possible key residues for inhibition of CGCYP51 by 19.

A comparative study of hydroxyl- and carboxylate-functionalized imidazolium and benzimidazolium salts as precursors for N-heterocyclic carbene ligands

The preparation of imidazolium and benzimidazolium salts with hydroxyl or carboxylate functions has been achieved using straightforward synthetic pathways. These salts in combination with palladium(II) acetate give active catalytic systems for Suzuki reac

Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids

Imidazolium and N-methyl-2-pyrrolidonium ionic liquids under ultrasound irradiation were developed as a green and expeditious approach for C-alkylation and N-alkylation of the nitrogen heterocycles including indoles and imidazoles with aliphatic and aroma

Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts

A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized β-amino compounds were synthesized by the hydroamination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M = Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA-15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives.

Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-throughput screen (HTS) for IDO1 inhibitors using the Prestwick Chemical Library of 1200 FDA-approved drugs and the Maybridge HitFinder Collection of 14,000 small molecules. Of the 60 hits selected for follow-up studies, 14 displayed IC50 values below 20 μM under the secondary assay conditions, and 4 showed an activity in cellular tests. In view of the high attrition rate we used both experimental and computational techniques to identify and to characterize compounds inhibiting IDO1 through unspecific inhibition mechanisms such as chemical reactivity, redox cycling, or aggregation. One specific IDO1 inhibitor scaffold, the imidazole antifungal agents, was chosen for rational structure-based lead optimization, which led to more soluble and smaller compounds with micromolar activity.