10045-65-5

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-1H-imidazole-2-carbaldehyde is used as a building block for the synthesis of pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs, potentially leading to innovative treatments and therapies.
Used in Agrochemical Industry:
1-Benzyl-1H-imidazole-2-carbaldehyde is used as a building block in the synthesis of agrochemicals. Its potential applications in this field can lead to the creation of new pesticides, herbicides, or other agricultural chemicals, enhancing crop protection and yield.
Used in Organic Chemistry Research:
1-Benzyl-1H-imidazole-2-carbaldehyde is used as a valuable compound in organic chemistry research. Its antimicrobial and antifungal properties make it an interesting subject for studying the mechanisms of action and potential applications in medicinal and agricultural research.

InChI:InChI=1/C11H10N2O/c14-9-11-12-6-7-13(11)8-10-4-2-1-3-5-10/h1-7,9H,8H2

Upstream product

• 4238-71-5 1-benzylimidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 100-39-0 benzyl bromide 
• 288-32-4 1H-imidazole 
• 5376-10-3 1-benzyl-2-(hydroxymethyl)imidazole 
• 10111-08-7 2-imidazolecarbaldehyde 
• 100-44-7 benzyl chloride 

Downstream Products

• 53798-70-2 1-(1-benzyl-1H-imidazol-2-yl)-3-[1,3]dioxolan-2-yl-propan-1-ol 
• 20062-64-0 1-benzyl-1H-imidazole-2-carbaldehyde thiosemicarbazone 
• 134221-23-1 C₁₂H₁₄N₆S 
• 134221-09-3 N'-[1-(1-Benzyl-1H-imidazol-2-yl)-meth-(E)-ylidene]-N,N-dimethyl-hydrazine 
• 102807-88-5 1-Benzyl-4'-trifluoromethyl-1H,1'H-[2,2']biimidazolyl 
• 25603-17-2 1-benzyl-2-[1,3]dioxolan-2-yl-1H-imidazole 
• 99809-02-6 2-(tert-butyldimethylsiloxy)-2-(1-benzyl-2-imidazolyl)thioacetamide 
• 99809-09-3 2-[(1-Benzyl-1H-imidazol-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-4-(2-methyl-1H-imidazol-4-yl)-thiazole; hydrobromide 
• 134221-21-9 N,N'-Bis-[1-(1-benzyl-1H-imidazol-2-yl)-meth-(E)-ylidene]-hydrazine 
• 134221-18-4 N-[1-(1-Benzyl-1H-imidazol-2-yl)-meth-(E)-ylidene]-N'-[1-(3-nitro-4-pentyloxy-phenyl)-eth-(E)-ylidene]-hydrazine 
• 134221-20-8 N,N'-Bis-[1-(3-nitro-4-pentyloxy-phenyl)-eth-(E)-ylidene]-hydrazine 
• 74531-38-7 1-Benzyl-5(1H)-oxoimidazo<1,2-a>pyridin-7-carbonsaeure-ethylester 
• 1207455-84-2 (E)-4-((1-benzyl-1H-imidazol-2-yl)methyleneamino)isobenzofuran-1(3H)-one 
• 1352710-08-7 C₂₁H₂₉N₃ 

Relevant academic research and scientific papers

Synthesis and electrochemical evaluation of 2-substituted imidazolium salts

Herein, we report the synthesis, electrochemical, and computational evaluation of six 2-substituted imidazolium bromides and six 2-substituted imidazolium triflates. All final compounds were obtained in 2 or fewer synthetic steps from inexpensive starting

Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations

New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.

Selection of chiral zinc catalysts for the kinetic resolution of esters via dynamic templating

Dynamic combinatorial libraries of chiral tetradentate bis-imine zinc(II) complexes have been prepared and screened for (1) their discrimination of enantiomeric picolinate esters and pyridyl phosphonate transition state analogs (TSAs) and (2) their cataly

Synthesis and antimicrobial profile of N-substituted imidazolium oximes and their monoquaternary salts against multidrug resistant bacteria

Two different series of N-substituted imidazolium oximes and their monoquaternary salts were synthesized and biologically tested with respect to their ability to inhibit growth a diverse panel of antibiotic susceptible Gram-positive and antibiotic resistant Gram-negative bacteria as well fungal strains. The newly synthesized compounds were analyzed by spectral studies to confirm their structure. The preliminary results showed that all compounds tested possess promising antimicrobial potential against both susceptible Gram-positive and antibiotic resistant Gram-negative isolates, exhibiting a wide range of MIC values from 0.14 to 100.0 μg/mL. The structure-activity relationship demonstrates that the p-methylphenyl and p-fluorophenyl groups in monoquaternary salts 6 and 7 attached directly to the imidazolium ring could be essential for observed remarkable inhibitory profiles against clinically important pathogens Pseudomonas aeruginosa (MIC = 0.14 μg/mL) and Klebsiella pneumoniae (MIC = 1.56 μg/mL). Furthermore, the broth microdilution assay was then used to investigate the antiresistance efficacy of compound 7 against fourteen extended-spectrum β-lactamase (ESBL)-producing strains in comparison to eight clinically relevant antibiotics. Compound 7 exhibited a remarkable antiresistance profiles ranging between 0.39 and 12.50 μg/mL against all of ESBL-producing strains, which leads to the suggestion that may be interesting candidate for development of new antimicrobials to combat multidrug resistant Gram-negative bacteria.

Novel Quinoline-Hepcidine Antagonists

The present invention relates to novel hepcidin antagonists of the general formula (I), pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for treatment of disorders in iron metabolism, such as, in particular, iron deficiency diseases and anaemias, in particular anaemias in connection with chronic inflammatory diseases (ACD: anaemia of chronic disease and AI: anaemia of inflammation).

Synthesis and biological evaluation of novel 2-(2-arylmethylene)hydrazinyl- 4-aminoquinazoline derivatives as potent antitumor agents

Two series of novel 2-(2-arylmethylene)hydrazinyl-4-aminoquinazoline derivatives were synthesized and evaluated for their cytotoxicity against H-460, HT-29, HepG2 and SGC-7901 cancer cell lines in vitro. Most compounds displayed moderate to excellent activity, with IC50 values ranging from 0.015 to 4.09 μM against all tested cell lines, respectively. The most promising compound 9p (E)-2-(2-((1-(2,3-dichlorobenzyl)-1H-imidazol-2-yl)methylene) hydrazinyl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine with IC50 values of 0.031 μM, 0.015 μM, 0.53 μM and 0.58 μM, which was 4- to 224 times more active than references 10 and Iressa, had emerged as a lead for further structural modifications.

Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives

A series of N-alkylimidazole-2-carboxylic acid, N-alkylimidazole-2- carboxaldehyde and N-alkylimidazole-2-methanol derivatives [alkyl = benzyl, methyl, ethyl, propyl, butyl, heptyl, octyl and decyl] have been synthesized and the protonation constants determined. The antimicrobial properties of the compounds were tested against Gram-negative (Escherichi coli), Gram-positive (Staphylococcus aureus & Bacillus subtilis subsp. spizizenii) bacterial strains and yeast (C. albicans). Both the disk diffusion and broth microdilution methods for testing the antimicrobial activity showed that N-alkylation of imidazole with longer alkyl chains and the substitution with low pKa group at 2-position resulted in enhanced antimicrobial activity. Particularly, the N-alkylimidazole-2-carboxylic acids exhibited the best antimicrobial activity due to the low pKa of the carboxylic acid moiety. Generally, all the N-alkylimidazole derivatives were most active against the Gram-positive bacteria [S. aureus (MIC = 5-160 μg mL-1) and B. subtilis subsp. spizizenii (5-20 μg mL-1)], with the latter more susceptible. All the compounds showed poor antimicrobial activity against both Gram-negative (E. coli, MIC = 0.15 to >2500 μg mL-1) bacteria and all the compounds were inactive against the yeast (Candida albicans).

METHODS OF USING DIHYDROPYRIDOPHTHALAZINONE INHIBITORS OF POLY (ADP-RIBOSE)POLYMERASE (PARP)

Provided herein are methods of treating cancer comprising administering a topoisomerase inhibitor, temozolomide, or a platin in combination with a Compound of Formula (I) or Formula (II), where the substituents Y, Z, A, B, R1, R2, R3, R4 and R5 are as defined herein.

Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand

A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).

DIHYDROPYRIDOPHTHALAZINONE INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE (PARP)

A compound having the structure set forth in Formula (I) and Formula (II): wherein the substituents Y, Z, A, B, R1, R2, R3, R4 and R5 are as defined herein. Provided herein are inhibitors of poly(ADP-ribose)polymerase activity. Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat diseases, disorders and conditions that are ameliorated by the inhibition of PARP activity.