112809-54-8

Usage

Uses

Due to the limited information available on 4-(1H-Imidazol-1-ylmethyl)benzonitrile, it is difficult to definitively list its applications. However, based on its chemical structure and the properties of similar benzimidazole compounds, potential uses may include:
Used in Pharmaceutical Industry:
4-(1H-Imidazol-1-ylmethyl)benzonitrile could be used as an intermediate in the synthesis of pharmaceutical compounds, given the prevalence of benzimidazoles in drug development. The fused benzene and imidazole rings may provide unique chemical properties that could be exploited in the design of new drugs.
Used in Chemical Research:
As a member of the benzimidazole family, 4-(1H-Imidazol-1-ylmethyl)benzonitrile may be used in academic or industrial research settings to study the properties and reactivity of benzimidazole compounds. This could lead to the discovery of new applications or the development of novel synthetic methods.
Used in Material Science:
The unique structure of 4-(1H-Imidazol-1-ylmethyl)benzonitrile may also make it a candidate for use in the development of new materials, such as polymers or coatings, that could benefit from the chemical characteristics of benzimidazoles.

InChI:InChI=1/C11H9N3/c12-7-10-1-3-11(4-2-10)8-14-6-5-13-9-14/h1-6,9H,8H2

Upstream product

• 288-32-4 1H-imidazole 
• 17201-43-3 4-cyanobenzyl bromide 

Downstream Products

• 311823-24-2 4-[4-(tert-butyl-dimethyl-silanyloxy)-1-imidazol-1-yl-butyl]-benzonitrile 
• 94084-75-0 4-(1H-imidazol-1-ylmethyl)benzoic acid 
• 112086-47-2 4-(1H-imidazol-1-yl)methylphenylmethanamine 
• 1345412-03-4 5-(3-Bromo-4-cyclopropoxy-phenyl)-3-(4-imidazol-1-ylmethyl-phenyl)-[1,2,4]oxadiazole 
• 1345411-98-4 3-(4-Imidazol-1-ylmethyl-phenyl)-5-(4-isopropoxy-3-nitro-phenyl)-[1,2,4]oxadiazole 
• 327058-57-1 Cd(4'-cyanobenzyl-1-imidazole)4(NO₃)2 
• 327058-60-6 Ni(4'-cyanobenzyl-1-imidazole)4(NO₃)2 
• 327058-59-3 Co(4'-cyanobenzyl-1-imidazole)4(NO₃)2 
• 56643-80-2 ethyl 4-((1H-imidazol-1-yl)methyl)benzoate 
• 139277-57-9 4-[(1H-imidazol-1-yl)-methyl]benzhydrazide 

Relevant academic research and scientific papers

Synthesis and biochemical evaluation of a range of potent benzyl imidazole-based compounds as potential inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)

The cytochrome P-450 enzyme, 17α-hydroxylase/17,20-lyase (P45017α), is a potential target in hormone-dependent cancers. Here, we report the synthesis and biochemical evaluation of a range of benzyl imidazole-based compounds which have been targeted against the two components of this enzyme, that is, 17α-hydroxylase (17α-OHase) and 17,20-lyase (lyase). The results from the biochemical testing suggest that the compounds synthesised are good inhibitors, with N-4-iodobenzyl imidazole (5) (IC50 = 10.06 μM against 17α-OHase and IC50 = 1.58 μM against lyase) showing equipotent activity against lyase compared to the standard compound, ketoconazole (KTZ) (IC50 = 3.76 ± 0.01 μM against 17α-OHase and IC50 = 1.66 ± 0.15 μM against lyase). Furthermore, the compounds tested are less potent towards the 17α-OHase component, a desirable property in the development of novel inhibitors of P45017α.

DEGRADABLE IMIDAZOLIUM OLIGOMER AND POLYMER FOR ANTIMICROBIAL APPLICATIONS

The present invention relates to an imidazolium oligomer of formula (I) and an imidazolium oligomer or a polymer of formula (II) where the various groups are as defined in the specification. The present invention also relates to the methods for their preparation, antimicrobial composition, antimicrobial gel containing these oligomers and/or polymers of Formula (I) and (II), and uses of these oligomers and/or polymers in the treatment of a microbial infection or disease.

Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors

A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole 1. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 μM), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen.

Synthesis, Biological Evaluation, and Molecular Modeling of 1 -Benzyl-1H-imidazoles as Selective Inhibitors of Aldosterone Synthase (CYP11B2)

Reducing aldosterone action is beneficial in various major diseases such as heart failure. Currently, this is achieved, with mineralocorticoid, receptor antagonists, however, aldosterone synthase (CYP 11B2) inhibitors may offer a promising alternative. In this study, we used three-dimensional modeling of CYP11B2 to model, the binding modes of the natural substrate 18-hydroxycorticosterone and the recently published CYP11B2 inhibitor R-fadrozole as a rational guide to design 44 structurally simple and achiral 1-benzyl-1H-imidazoles. Their syntheses, in vitro inhibitor potencies, and in silico docking are described. Some promising CYP11B2 inhibitors were identified, with our novel lead, MOERAS 115 (4-((5-phenyl-1H-imidazol-1-yl)methyl) benzonitrile) displaying an IC50 for CYP11B2 of 1.7 nM, and a CYP11B2 (versus CYP11B1) selectivity of 16.5, comparable to R-fadrozole (IC 50 for CYP11B26.0 nM, selectivity 19.8). Molecular docking of the inhibitors in the models enabled us to generate posthoc hypotheses on their binding modes, providing a valuable basis for future studies and further design of CYP11B2 inhibitors.

Synthesis of conformationally constrained 5,6,7,8-tetrahydroimidazo[1,5-a]pyridine inhibitors of Farnesyltransferase

(Equation Presented) Synthesis of the 8-amino-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine ring system was accomplished by intramolecular cyclization of an iminium ion, derived from condensation of an amine and a substituted γ-(1-imidazolyl)butyraldehyde. The

INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE

The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase

New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o,m,p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m-substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.

ALPHA-HETEROCYCLC SUBSTITUTED TOLUNITRILES

The invention is concerned with aromatase inhibiting compounds of formula I wherein R and Ro represent hydrogen or lower alkyl; or R and Ro located on adjacent carbon atoms and together when combined with the benzene ring to which they are attached form a naphthalene or tetrahydronaphthalene ring; R1 and R2 independently represent hydrogen, lower alkyl, (lower alkyl, aryl or aryl-lower alkyl)-thio, lower alkenyl, aryl, aryl-lower alkyl, C3-C6-cycloalkyl, or C3-C6-cycloalkyl-lower alkyl; or R1 and R2 combined represent lower alkylidene, mono or di-aryl-lower alkylidene; R1 and R2 combined also represent C4-C6-straight chain alkylene, lower alkyl-substituted straight chain alkylene or ortho-phenylene bridged-C2-C4 -straight chain alkylene, each forming with the carbon atom attached thereto a corresponding optionally substituted or benzo-fused 5, 6 or 7-membered ring; W represents 1-imidazolyl, 1-(1,2,4- or 1,3,4)-triazolyl or 3-pyridyl; or W represents 1-imidazolyl, 1-(1,2,4 or 1,3,4)-triazolyl or 3-pyridyl substituted by lower alkyl; and pharmaceutically acceptable salts thereof

Alpha-heterocycle substituted tolunitriles

The invention is concerned with aromatase inhibiting compounds of formula I STR1 where R and Ro represent hydrogen or lower alkyl; or R and Ro located on adjacent carbon atoms and together when combined with the benzene ring to which they are attached for