56643-95-9

Upstream product

• 288-32-4 1H-imidazole 
• 824-94-2 p-methoxybenzyl chloride 
• 95460-09-6 1-(4-methoxybenzyl)imidazole-2-thione 
• 105-13-5 4-Methoxybenzyl alcohol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 2746-25-0 p-Methoxybenzyl bromide 
• 104-93-8 p-methylanizole 

Downstream Products

• 95460-12-1 1-(4-methoxybenzyl)-1H-imidazole-2-carbaldehyde 
• 41833-17-4 4-[(1-imidazolyl)methyl]phenol 
• 936216-40-9 2-iodo-1-(4-methoxybenzyl)-1H-imidazole 
• 861162-53-0 2-ethyl-1-[1-(4-methoxybenzyl)-1H-imidazol-2-yl]butan-1-ol 

Relevant academic research and scientific papers

Antifungal activity of 1,4-dialkoxynaphthalen-2-acyl imidazolium salts by inducing apoptosis of pathogenic candida spp.

Even though Candida spp. are staying commonly on human skin, it is also an opportunistic pathogenic fungus that can cause candidiasis. The emergence of resistant Candida strains and the toxicity of antifungal agents have encouraged the development of new classes of potent antifungal agents. Novel naphthalen-2-acyl imidazolium salts (NAIMSs), especially 1,4-dialkoxy-NAIMS from 1,4-dihydroxynaphthalene, were prepared and evaluated for antifungal activity. Those derivatives showed prominent anti-Candida activity with a minimum inhibitory concentration (MIC) of 3.125 to 6.26 μg/mL in 24 h based on microdilution antifungal susceptibility test. Among the tested com-pounds, NAIMS 7c showed strongest antifungal activity with 3.125 μg/mL MIC value compared with miconazole which showed 12.5 μg/mL MIC value against Candida spp., and more importantly >100 μg/mL MIC value against C. auris. The production of reactive oxygen species (ROS) was increased and JC-1 staining showed the loss of mitochondrial membrane potential in C. albicans by treatment with NAIMS 7c. The increased release of ultraviolet (UV) absorbing materials suggested that NAIMS 7c could cause cell busting. The expression of apoptosis-related genes was induced in C. albicans by NAIMS 7c treatment. Taken together, the synthetic NAIMSs are of high interest as novel antifungal agents given further in vivo examination.

Simple and rapid p-methoxybenzylation of hydroxy and amide groups at room temperature by NaOt-Bu and DMSO

The p-methoxybenzylation of hydroxy and amide groups by p-methoxybenzyl chloride utilizing NaOt-Bu in DMSO is described. p-Methoxybenzylation of sterically hindered menthol using NaOt-Bu in DMSO proceeded faster than the commonly used methods which use Na

Synthesis and investigation of inhibitory activities of imidazole derivatives against the metallo-β-lactamase IMP-1

Mutations in bacteria can result in antibiotic resistance due to the overuse or abuse of β-lactam antibiotics. One strategy which bacteria can become resistance toward antibiotics is secreting of metallo β-lactamase enzymes that can open the lactam ring of the β-lactam antibiotic and inactivate them. This issue is a threat for human health and one strategy to overcome this situation is co-administration of β-lactam antibiotics with an inhibitor. So far, no clinically available inhibitors of metallo β-lactamases (MBLs) reported and the clinically inhibitors of serine β-lactamase are useless for MBLs. Accordingly, finding a potent inhibitor of the MBLs being very important. In this study, imidazole derivatives primarily were synthesized and their inhibitory activity were measured. Later in silico binding model was used to predict the configuration and conformation of the ligands into the active site of enzyme. Two molecules demonstrated with IC50 of 39 μM and 46 μM against MBL (IMP-1).

Direct C-N coupling of imidazoles with aromatic and benzylic compounds via electrooxidative C-H functionalization

A method for the C-N coupling of imidazoles based on electrooxidative C-H functionalization of aromatic and benzylic compounds has been developed. The key to the success is the formation of protected imidazolium ions as initial products, avoiding overoxidation. Deprotection under nonoxidative conditions affords N-substituted imidazoles. Various functional groups are compatible with the present transformation. To demonstrate the power of the method, a P450 17 inhibiter and an antifungal agent having N-substituted imidazole structures were synthesized.

Synthesis of imidazole derivatives with antimycobacterial activity

4-Substituted 1-(p-methoxybenzyl)imidazoles were designed and synthesized in order to mimic parts of the structure of highly potent antimycobacterial 6-aryl-9-(p-methoxybenzyl)purines. 4-Haloimidazoles were subjected to Pd-catalyzed cross-coupling in order to introduce a (hetero)-aryl group, or they were converted to Grignard reagents and reacted with (hetero)arylaldehydes. Further transformations of the adducts gave a variety of potential antimycobacterials with different "spacers" between the imidazole and (hetero)aryl group. The adduct from furfural was rearranged to a cyclopentenone derivative when treated with methanol under acidic conditions. Several target compounds exhibited antimycobacterial activity in vitro (IC90 13 μg/mL for the best inhibitors), but they were not as active as the most potent purines and pyrimidines synthesized before.

Synthesis and structure-activity relationship of a novel series of heterocyclic sulfonamide γ-secretase inhibitors

γ-Secretase inhibitors have been shown to reduce the production of β-amyloid, a component of the plaques that are found in brains of patients with Alzheimer's disease. A novel series of heterocyclic sulfonamide γ-secretase inhibitors that reduce β-amyloid levels in cells is reported. Several examples of compounds within this series demonstrate a higher propensity to inhibit the processing of amyloid precursor protein compared to Notch, an alternative γ-secretase substrate.

Palladium-catalyzed intramolecular arylation of N-benzyl-2-iodoimidazoles: A facile and rapid access to 5H-imidazo[2,1-α]isoindoles

The first example of a Pd-catalyzed intramolecular arylation involving the C-2 position of an imidazole ring is presented. Application of this reaction led to the formation of 5H-imidazo[2,1-a]isoindole in one step from N-benzyl-2-iodoimidazole. Microwave irradiation enhanced the rate of reaction allowing the synthesis of various imidazo[2,1-a]isoindole analogues. Georg Thieme Verlag Stuttgart.

The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazoles

The reactions of non-benzylic primary and secondary aliphatic alcohols with carbonyldiimidazole (CDI) afford the corresponding carbamates but not N-alkylimidazoles. For benzylic primary alcohols, formation of N-alkylimidazoles proceeds reasonably at 170 °C in several different solvents and occurs by way of the initially formed carbamate. However, under these rather forcing conditions, or even at lower reaction temperatures, elimination is a significant side reaction for benzylic secondary alcohols with β-hydrogen atoms. With one exception, reactions of six N,N-disubstituted β-aminoalcohols with CDI to form N-alkylimidazoles proceed under relatively mild conditions and may occur by way of an aziridinium intermediate.

1-Methyl-3-trimethylsilylparabanic acid as an effective reagent for the preparation of N-substituted (1-methyl-2,5-dioxo-1,2,5H-imidazolin-4-YL)-amines and its application to the total synthesis of isonaamidines A and C, antitumor imidazole alkaloids

1-Methyl-3-trimethylsilylparabanic acid (17) was successfully used in the final step of the total synthesis of isonaamidine A (9), isonaamidine C (11) and pyronaamidine (8), antitumor marine imidazole alkaloids.

NOVEL COMPOUNDS USEFUL AS NEURO-PROTECTIVE AGENTS

This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.