80304-50-3

Usage

Uses

Used in Pharmaceutical Research:
1-Benzyl-5-hydroxymethyl-1H-imidazole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable building block for the development of new drugs with diverse therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 1-benzyl-5-hydroxymethyl-1H-imidazole serves as a versatile reagent and catalyst. Its ability to participate in various chemical reactions, such as condensation, cyclization, and substitution, makes it a useful component in the preparation of complex organic molecules.
Used in Antifungal and Antibacterial Applications:
1-Benzyl-5-hydroxymethyl-1H-imidazole has been studied for its potential use as an antifungal and antibacterial agent. Its ability to inhibit the growth of various pathogenic microorganisms makes it a promising candidate for the development of new antimicrobial agents to combat drug-resistant infections.
Used in Neurological Disorder Treatment:
1-BENZYL-5-HYDROXYMETHYL-1H-IMIDAZOLE has been investigated for its potential role in the treatment of neurological disorders. Its ability to modulate specific biological pathways and target cellular mechanisms involved in neurodegenerative diseases positions it as a potential therapeutic agent for conditions such as Alzheimer's, Parkinson's, and multiple sclerosis.
Used in Anticancer Applications:
1-Benzyl-5-hydroxymethyl-1H-imidazole has also been explored as a potential anticancer agent. Its capacity to interfere with cancer cell growth, proliferation, and survival pathways suggests its potential use in the development of novel cancer therapies, either as a standalone treatment or in combination with existing chemotherapeutic drugs.

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

Upstream product

• 822-55-9 (1H-imidazol-4-yl)methanol 
• 100-39-0 benzyl bromide 
• 76075-21-3 ethyl 1-benzyl-1H-imidazole-5-carboxylic acid 
• 98412-23-8 1-benzyl-2-mercapto-5-hydroxymethyl-imidazole 
• 626242-04-4 (1-benzyl-1H-5-imidazolyl)methyl acetate 
• 91025-37-5 ethyl 3-benzyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-4-carboxylate 
• 1609282-78-1 1-benzyl-2-(methylthio)-5-imidazolcarbonitrile 
• 287198-16-7 3-benzyl-2-(methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one 
• 39123-65-4 3-benzyl-2-thioxotetrahydro-4H-imidazol-4-one 
• 100-44-7 benzyl chloride 
• 1399859-85-8 N-benzyl-N'-(2'-acetamido)thiourea 
• 100-46-9 benzylamine 
• 160999-35-9 1-Benzyl-5-(2-phenylethenyl)-1H-imidazole 
• 60293-41-6 N-((E)-3-phenylallylidene)benzylamine 

Downstream Products

• 82830-36-2 1-Benzyl-5-(chloromethyl)-1H-imidazolium chloride 
• 784182-26-9 1-benzyl-5-chloromethyl-1H-imidazole 
• 880106-38-7 4-[N-(1-benzyl-1H-imidazol-5-yl)methylamino]-2-phenylbenzoylmethionine methyl ester 
• 1417526-45-4 N-((1-benzyl-1H-imidazol-5-yl)methyl)-N-ethylethanamine 
• 73941-33-0 methyl 1-benzyl-1H-imidazole-5-carboxylate 
• 76075-21-3 ethyl 1-benzyl-1H-imidazole-5-carboxylic acid 
• 86803-31-8 1-benzyl-5-vinyl-1H-imidazole 
• 182965-61-3 1-Benzyl-5-((E)-2-nitro-2-phenyl-vinyl)-1H-imidazole 
• 186502-01-2 (S)-4-Benzyl-3-[(S)-2-(3-benzyl-3H-imidazol-4-yl)-2-(tert-butyl-dimethyl-silanyloxy)-acetyl]-oxazolidin-2-one 

Relevant academic research and scientific papers

A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives

A simple yet robust flow set-up for the efficient desulfurization of a series of thioimidazoles is presented, which generates the corresponding imidazole derivatives in high yields. The strategic choice of peristaltic over piston pumps allowed reliable delivery of the heterogeneous stream of the thioimidazole substrate into a T-piece where it reacted with NaNO2 in the presence of acetic acid. This approach enabled the controlled and safe formation of the reactive nitrosonium species without uncontrolled exposure to hazardous nitrous oxide by-products as observed in related batch protocols. The value of the resulting imidazole products was further demonstrated by their conversion into various esters representing new derivatives of the known analgesic etomidate through an efficient one-pot Corey–Gilman–Ganem oxidation procedure.

AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE

The present invention relates to the filed of pharmarcutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) amd a preparation method thereof, a pharmarcutical composition with the compounds as active components, and a use of the azole compounds and the pharmarcutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as deinfed in the specifictaion.

AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE

The present invention relates to the field of pharmaceutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) and a preparation method thereof, a pharmaceutical composition with the compounds as active components, and a use of the azole compounds and the pharmaceutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as defined in the specification.

Preparation of 2'-13c-l-histidine starting from 13c-thiocyanate: Synthetic access to any site-directed stable isotope enriched l-histidine

1-Benzyl-2-(methylthio)-imidazole-5-ketone is obtained in a few simple steps starting from thiocyanate and glycine amide (glycin). Subsequent treatment with diethyl phosphorocyanidate and functional group manipulations gives 1-benzyl-5-chloromethylimidazolium chloride. This compound is converted under mild O'Donnell conditions into the corresponding L-histidine derivative. After deprotection L-histidine is obtained in good yield and 99% enantiomeric excess. 2'-13C-L-Histidine has been obtained via this new scheme with high (99%) 13C incorporation starting with commercially available 13C- thiocyanate. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives.

Structure-based design of imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase

A series of imidazole-containing peptidomimetic PFTase inhibitors and their co-crystal structures bound to PFTase and FPP are reported. The structures reveal that the peptidomimetics adopt a similar conformation to that of the extended CVIM tetrapeptide,

Novel N-(4-piperidinyl)benzamide antimalarials with mammalian protein farnesyltransferase inhibitory activity

Protein farnesyltransferase of Plasmodium falciparum is a potential target in the treatment of malaria for which increased drug resistance is observed. The design, synthesis and evaluation of a series of N-(4-piperidinyl)benzamides is reported. The most potent compounds showed in vitro activity against the parasite at submicromolar concentrations.

Potent and selective farnesyl transferase inhibitors

We recently described a novel series of CA1A2X peptidomimetics as farnesyl transferase inhibitors (FTIs). These compounds possess an N-(4-piperidinyl)benzamide scaffold mimicking A1A 2 residue. Extensive exploration of structure-activity relationships revealed that replacement of cysteine by substituted benzylimidazoles provided nanomolar FTIs with in vitro activities (18e, IC50 = 4.60 nM on isolated enzyme, EC50 = 20.0 nM for growth inhibition on a tumor cell line). The molecular docking of 18e and 19e in the active site of the enzyme provided details of key interactions with the protein and showed that the methionine or phenylalanine residue fits into the aryl binding site.

Parallel liquid synthesis of N,N′-disubstituted 3-amino azepin-2-ones as potent and specific farnesyl transferase inhibitors

A rapid structure-activity study was performed by parallel liquid synthesis on N,N′-disubstitution of 3-amino azepin-2-one to afford potent and specific farnesyl transferase inhibitors with low nM enzymatic and cellular activities. The activities of the selected compounds were validated in vivo, and compounds 41a and 44a presented significant antitumour activity.

Preparation of a clinically investigated ras farnesyl transferase inhibitor

The synthesis of ras farnesyl-protein transferase inhibitor 1 is described on a multi-kilogram scale. Retrosynthetic analysis reveals chloromethylimidazole 2 and a piperazinone 3 as viable precursors. The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoimidazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new Mitsunobu cyclization strategy was developed to prepare the arylpiperazinone fragment 3.

Process for preparing a 1-substituted 5-hydroxymethyl imidazole

A process for preparing a 1-substituted 5-hydroxymethylimidazole of the formula: , wherein R represents alkyl, hydroxyalkyl, allyl, or substituted or unsubstituted arylmethyl or diarylmethyl, comprising the step of reacting a 1-substituted 2-mercapto-5-hy