72459-47-3

Basic information

• Product Name: 1-(3-BROMOBENZYL)-1H-IMIDAZOLE
• Synonyms: 1-(3-BROMOBENZYL)-1H-IMIDAZOLE;1-(3-Bromobenzyl)-1H-imidazole 97%
• CAS NO: 72459-47-3
• Molecular Formula: C₁₀H₉BrN₂
• Molecular Weight: 237.1
• Mol File: 72459-47-3.mol

Chemical Properties

• Melting Point: 62 °C
• Boiling Point: 371.455°C at 760 mmHg
• Flash Point: 178.45°C
• Appearance: /
• Density: 1.441g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 1-(3-BROMOBENZYL)-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-BROMOBENZYL)-1H-IMIDAZOLE(72459-47-3)
• EPA Substance Registry System: 1-(3-BROMOBENZYL)-1H-IMIDAZOLE(72459-47-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 72459-47-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(3-BROMOBENZYL)-1H-IMIDAZOLE is used as a building block in organic synthesis for its reactivity, allowing for the formation of new bonds with other molecules, which is crucial in creating a wide range of chemical compounds.
Used in Pharmaceutical Industry:
1-(3-BROMOBENZYL)-1H-IMIDAZOLE is used as a precursor in the development of pharmaceuticals due to its potential to be incorporated into drug molecules, contributing to their therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(3-BROMOBENZYL)-1H-IMIDAZOLE is used as a starting material for the synthesis of various agrochemicals, potentially enhancing the effectiveness of pesticides and other agricultural chemicals.
Used in Materials Science:
1-(3-BROMOBENZYL)-1H-IMIDAZOLE is utilized in materials science for its potential to contribute to the development of new materials with specific properties, such as those with enhanced stability or reactivity.
Safety Note:
It is important to handle 1-(3-BROMOBENZYL)-1H-IMIDAZOLE with care due to its potential hazards and risks. Proper safety measures, including the use of personal protective equipment and adherence to safety protocols, should be strictly followed when working with this chemical compound.

InChI:InChI=1/C10H9BrN2/c11-10-3-1-2-9(6-10)7-13-5-4-12-8-13/h1-6,8H,7H2

Upstream product

• 288-32-4 1H-imidazole 
• 823-78-9 meta-bromobenzyl bromide 
• 591-17-3 meta-bromotoluene 

Downstream Products

• 1426937-33-8 C₁₇H₁₆N₄O₂ 
• 1426937-34-9 C₁₇H₁₇N₃O 
• 1426937-35-0 C₁₈H₁₇ClN₂O 
• 1426937-36-1 C₂₂H₁₈N₂O 
• 1426937-37-2 C₁₈H₁₈N₂O 
• 1426937-38-3 C₁₇H₁₆N₂O 
• 1426937-39-4 C₁₆H₁₃ClN₂O 
• 1426937-40-7 C₁₇H₁₆N₂O 
• 111371-15-4 C₁₆H₁₄N₂O 
• 912962-74-4 3-(3-((1H-imidazol-1-yl)methyl)phenyl)-N-(tert-butyl)-5-isobutylthiophene-2-sulfonamide 

Relevant articles and documents

A convenient transesterification method for synthesis of AT2 receptor ligands with improved stability in human liver microsomes

A series of AT2R ligands have been synthesized applying a quick, simple, and safe transesterification-type reaction whereby the sulfonyl carbamate alkyl tail of the selective AT2R antagonist C38 was varied. Furthermore, a limited number of compounds where acyl sulfonamides and sulfonyl ureas served as carboxylic acid bioisosteres were synthesized and evaluated. By reducing the size of the alkyl chain of the sulfonyl carbamates, ligands 7a and 7b were identified with significantly improved in vitro metabolic stability in both human and mouse liver microsomes as compared to C38 while retaining the AT2R binding affinity and AT2R/AT1R selectivity. Eight of the compounds synthesized exhibit an improved stability in human microsomes as compared to C38.

Interconversion of functional activity by minor structural alterations in nonpeptide AT2 receptor ligands

Migration of the methylene imidazole side chain in the first reported selective drug-like AT2 receptor agonist C21/M024 (1) delivered the AT2 receptor antagonist C38/M132 (2). We now report that the AT2 receptor antagonist compound 4, a biphenyl derivative that is structurally related to 2, is transformed to the agonist 6 by migration of the isobutyl group. The importance of the relative position of the methylene imidazole and the isobutyl substituent is highlighted herein.

CYCLOALKYL NITRILE PYRAZOLO PYRIDONES AS JANUS KINASE INHIBITORS

Compounds of formula I are provided, which are JAK inhibitors and are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.

Antitrypanosomal lead discovery: Identification of a ligand-efficient inhibitor of Trypanosoma cruzi CYP51 and parasite growth

Chagas disease is caused by the intracellular protozoan parasite Trypanosomal cruzi, and current drugs are lacking in terms of desired safety and efficacy profiles. Following on a recently reported high-throughput screening campaign, we have explored initial structure-activity relationships around a class of imidazole-based compounds. This profiling has uncovered compounds 4c (NEU321) and 4j (NEU704), which are potent against in vitro cultures of T. cruzi and are greater than 160-fold selective over host cells. We report in vitro drug metabolism and properties profiling of 4c and show that this chemotype inhibits the T. cruzi CYP51 enzyme, an observation confirmed by X-ray crystallographic analysis. We compare the binding orientation of 4c to that of other, previously reported inhibitors. We show that 4c displays a significantly better ligand efficiency and a shorter synthetic route over previously disclosed CYP51 inhibitors, and should therefore be considered a promising lead compound for further optimization.

CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES AS JANUS KINASE INHIBITORS

Cycloalkylnitrile pyrazole carboxamides as JAK inhibitors useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer are provided.

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.

C17,20-lyase inhibitors I. Structure-based de novo design and SAR study of C17,20-lyase inhibitors.

Novel nonsteroidal C(17,20)-lyase inhibitors were synthesized using de novo design based on its substrate, 17 alpha-hydroxypregnenolone, and several compounds exhibited potent C(17,20)-lyase inhibition. However, in vivo activities were found to be short-lasting, and in order to improve the duration of action, a series of benzothiophene derivatives were evaluated. As a result, compounds 9h, (S)-9i, and 9k with nanomolar enzyme inhibition (IC(50)=4-9 nM) and 9e (IC(50)=27 nM) were identified to have powerful in vivo efficacy with extended duration of action. The key structural determinants for the in vivo efficacy were demonstrated to be the 5-fluoro group on the benzothiophene ring and the 4-imidazolyl moiety. Superimposition of 9k and 17 alpha-hydroxypregnenolone demonstrated their structural similarity and enabled rationalization of the pharmacological results. In addition, selected compounds were also identified to be potent inhibitors of human enzyme with IC(50) values of 20-30 nM.