85102-93-8

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzylimidazole-4-carbaldehyde is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds.
Used in Dye Industry:
In the dye industry, 1-benzylimidazole-4-carbaldehyde is utilized as an intermediate, playing a crucial role in the production of various dyes due to its chemical properties that can impart color and stability.
Used in Organic Chemistry Research:
1-Benzylimidazole-4-carbaldehyde serves as a versatile building block in organic chemistry, used for the development of new materials and chemical processes, showcasing its importance in scientific research and innovation.
Used in Antimicrobial and Antifungal Applications:
Although its use in this area is still under study, 1-benzylimidazole-4-carbaldehyde has shown potential as an antimicrobial and antifungal agent, indicating possible applications in healthcare and related industries for infection control and prevention.

Upstream product

• 100-39-0 benzyl bromide 
• 3034-50-2 4⁽⁵⁾formylimidazole 
• 10111-08-7 2-imidazolecarbaldehyde 
• 3034-50-2 5-imidazolecarboxaldehyde 
• 100-44-7 benzyl chloride 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 
• 17674-16-7 benzyl triflate 
• 118004-64-1 1-[2-(trimethylsilyl)ethoxymethyl]imidazole-5-carboxaldehyde 
• 85102-84-7 N¹-Benzyl-4-hydroxymethylimidazole 

Downstream Products

• 94128-88-8 C₁₂H₁₃N₅S 
• 1122649-19-7 3-endo-[8-(1-benzyl-1H-imidazol-4-ylmethyl)-8-aza-bicyclo[3.2.1]oct-3-yl]benzamide 
• 1352929-61-3 C₁₅H₁₃N₃O₂ 
• 880106-37-6 4-[N-(1-benzyl-1H-imidazol-4-yl)methylamino]-2-phenylbenzoylmethionine methyl ester 
• 86803-30-7 1-benzyl-4-ethenyl-1H-imidazole 

Relevant academic research and scientific papers

Design, synthesis and biological activities of 2,3-dihydroquinazolin-4(1H)-one derivatives as TRPM2 inhibitors

Transient receptor potential melastatin 2 (TRPM2), a Ca2+-permeable cationic channel, plays critical roles in insulin release, cytokine production, body temperature regulation and cell death as a reactive oxygen species (ROS) and temperature sensor. However, few TRPM2 inhibitors have been reported, especially TRP-subtype selective inhibitors, which hampers the investigation and validation of TRPM2 as a drug target. To discover novel TRPM2 inhibitors, 3D similarity-based virtual screening method was employed, by which 2,3-dihydroquinazolin-4(1H)-one derivative H1 was identified as a TRPM2 inhibitor. A series of novel 2,3-dihydroquinazolin-4(1H)-one derivatives were subsequently synthesized and characterized. Their inhibitory activities against the TRPM2 channel were evaluated by calcium imaging and electrophysiology approaches. Some of the compounds exhibited significant inhibitory activity, especially D9 which showed an IC50 of 3.7 μM against TRPM2 and did not affect the TRPM8 channel. The summarized structure-activity relationship (SAR) provides valuable insights for further development of specific TRPM2 targeted inhibitors.

Supported TBD-assisted solution phase diversification of formyl-aza-heterocycles through alkylation-knoevenagel one pot sequences

An efficient solution-phase parallel procedure to perform the structural diversification of some formyl-nitrogen heterocycles (A) using the reusable TBD supported base is described. The library synthesis is based in a consecutive Alkylation-Knoevenagel functionalisation that uses alkyl halides (B), Michael acceptors (C) and activated methylene compounds (D) as diversity elements.

Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists

The invention provides heteroarylene substituted 8-azabicyclo[3.2.1]octane compounds of formula (I): wherein R1, R2, A, and m are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are antagonists at th

Regiochemistry of N-substitution of some 4(5)-substituted imidazoles under solvent-free conditions

(Chemical Equation Presented) Imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole were N-benzylated and N-methylated using benzyl chloride and methyl iodide on zinc oxide (ZnO), alumina, and KF/alumina under basic conditions without solvent. Triethylamine (Et3N) or potassium carbonate was added as base in the reactions on ZnO and alumina. Imidazole-4(5)-carboxaldehyde was also benzylated on silica and carbon nanotubes. The effect of bases and solids on the product distribution of 1,4- and 1,5-substituted compounds was investigated. In some cases, the product ratios were different for imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole. In the reactions on KF/alumina the 1,4-product was favored for both compounds. The combination of Et3N and ZnO favored the 1,5-product, however for the nitrile effect was not so pronounced. When N-benzylation and methylation of the aldehyde were performed in the presence of catalytic amount of zinc chloride with Et3N as base, the product distributions were the same as in the reactions on ZnO. Nitrile gave different product ratios on ZnO and in the presence of ZnCl2. In addition, a mixture of N-benzylimidazole and 1,3-dibenzylimidazolium was produced when imidazole was benzylated on KF/alumina. Only the latter product was afforded when two equivalents of benzyl chloride were used.

Regioselective alkylation of 2-alkyl-5,6,7,8-tetrahydro-3H- cycloheptimidazol-4-ones and 2-alkyl-3H-cycloheptimidazol-4-ones

Regioselective alkylation of 2-alkyl-5,6,7,8-tetrahydro-3H- cycloheptimidazol-4-one (1) and 2-alkyl-3H-cycloheptimidazol-4-one (2) was investigated. 3-[2′-(1-tert-Butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-2- propyl-5,6,7,8-tetrahydro-1H-cycloheptimidazol-4-one (6) was preferentially obtained under the conditions by using NaH in DMF or THF. On the other hand, 3-[2′-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-2-propyl-5,6,7, 8-tetrahydro-3H-cycloheptimidazol-4-one (5), the synthetic intermediate compound of Pratosartan, was obtained selectively in the presence of n-Bu4NBr in toluene by using aqueous sodium hydroxide as a base. In this reaction, it was found that the concentration of the alkaline solution influences its regioselectivity. This selectivity was observed even for aldehyde and ester 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,

REGIOSPECIFIC SYNTHESIS OF N-ALKYL-4- AND 5-SUBSTITUTED IMIDAZOLES

A facile regiospecific synthesis of 4- and 5-substituted N-alkyl imidazoles has been developed from N-trimethylsilyloxyethylimidazole(s).The method combines directed metallation with alkyl triflate mediated imidazole quaternization and SEM group cleavage.

Synthesis of 4(5)-Acyl-, 1-Substituted 5-Acyl, and 1-Substituted 4-Acyl-1H-imidazoles from 4-Aminoisoxazoles

4-Aminoisoxazoles can be acylated with a wide variety of activated carboxylic acids.Hydrogenation of the resulting amides gives α-(acylamino)enaminones, which cyclize to 4(5)-acylimidazoles upon treatment with base.This method allows for the synthesis of acylimidazoles with a wide range of substituents at C-2.Utilization of N-substituted 4-aminoisoxazoles in the same sequence of reactions yields 1-substituted 5-acylimidazoles, a substitution pattern not otherwise easily prepared.Treatment of α-(acylamino)enaminones, derived from N-unsubstituted isoxazoles, with primary amines leads to incorporation of the amine at the β-position with concomitant expulsion of ammonia.This sequence efficiently yields 1-substituted and 1,2-disubstituted 4-acylimidazoles but does not give satisfactory yields of 5-substituted 4-acylimidazoles due to steric inhibition of the amine exchange.