42032-27-9

Basic information

• Product Name: 1-(4-CHLOROBENZYL)-1H-IMIDAZOLE
• Synonyms: 1-(4-CHLOROBENZYL)-1H-IMIDAZOLE;1-(4-Chlorobenzyl)imidazole
• CAS NO: 42032-27-9
• Molecular Formula: C₁₀H₉ClN₂
• Molecular Weight: 192.64
• Mol File: 42032-27-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-CHLOROBENZYL)-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLOROBENZYL)-1H-IMIDAZOLE(42032-27-9)
• EPA Substance Registry System: 1-(4-CHLOROBENZYL)-1H-IMIDAZOLE(42032-27-9)

Safety Data

• Hazardous Substances Data: 42032-27-9(Hazardous Substances Data)

Upstream product

• 288-32-4 1H-imidazole 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 

Downstream Products

• 936216-46-5 1-(4-chlorobenzyl)-2-iodo-1H-imidazole 
• 1352953-03-7 1,1'-di(4-chlorobenzyl)-1H,1'H-2,2'-biimidazole 
• 109483-82-1 4-Chlorophenyl-1-(1-hydroxycyclohexyl)-1-imidazolylmethane 
• 99369-46-7 1-[1-Benzyl-1-(4-chloro-phenyl)-2-phenyl-ethyl]-1H-imidazole; compound with naphthalene-1,5-disulfonic acid 
• 99369-28-5 1-[1-(4-Chloro-phenyl)-2-phenyl-ethyl]-1H-imidazole; compound with naphthalene-1,5-disulfonic acid 
• 99369-27-4 1-(4-Chlorophenyl)-1-(1-imidazolyl)-2-phenylethane 
• 99369-45-6 2-(4-Chlorophenyl)-2-(1-imidazolyl)-1,3-diphenylpropane 
• 49823-18-9 [1-(4-chloro-benzyl)-1H-imidazol-2-yl]-bis-(4-chloro-phenyl)-methanol 

Relevant articles and documents

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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).

Novel imidazole aldoximes with broad-spectrum antimicrobial potency against multidrug resistant gram-negative bacteria

In the search for a new class of potential antimicrobial agents, five novel N-substituted imidazole 2-aldoximes and their six quaternary salts were evaluated. The antimicrobial activity was assessed against a panel of representative Gram-positive and Gram-negative bacteria, including multidrug resistant bacteria. All compounds demonstrated potent in vitro activity against the tested microorganisms, with MIC values ranging from 6.25 to 50.0 μg/mL. Among the tested compounds, two quaternary compounds (N-but-3-enyl- and meta- (10) or para- N-chlorobenzyl (11) imidazolium 2-aldoximes) displayed the most potent and broad-spectrum activity against both Gram-positive and Gram-negative bacterial strains. The broth microdilution assay was also used to investigate the antiresistance efficacy of the both most active compounds against a set of Enterobacteriaceae isolates carried a multiple extended-spectrum β-lactamases (ESBLs) in comparison to eight clinically relevant antibiotics. N-but-3-enyl-N-meta-chlorobenzyl imidazolium 2-aldoxime was found to possess promising antiresistance efficacy against a wide range of β-lactamases producing strains (MIC 2.0 to 16.0 μg/mL). Best results for that compound were obtained against Escherichia coli and Enterobacter cloacae producing multiple β-lactamases form A and C molecular classes, which were 32- and 128-fold more potent than ceftazidime and cefotaxime, respectively. To visualize the results, principal component analysis was used as an additional classification tool. The mixture of ceftazidime and compound 10 (3 μg:2 μg) showed a strong activity and lower the necessary amount (up to 40-fold) of 10 against five of ESBL-producing isolates (MIC ≤ 1 μg/mL).

First selective CYP11B1 inhibitors for the treatment of cortisol-dependent diseases

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An improved and convenient procedure for the synthesis of 1-substituted imidazoles

1-Protected imidazoles, such as 1-acetyl- and 1-benzoylimidazoles, react with various halides, such as benzyl, allyl, α-keto, and alkyl halides, to give 1-protected-3-substituted imidazolium salts in high yields. The resultant imidazolium salts are easily deprotected by treatment with water or alcohols to give the corresponding 1-substituted imidazoles in excellent yields. In this reaction the yields of 1-substituted imidazoles vary with the kinds of halides used and/or with the protecting groups, and the yields increase in the following order: benzyl halides≥allyl halides~α-keto halides>alkyl halides, and acetyl≥benzoyl>ethoxycarbonyl>diethoxymethyl>trimethylsilyl>tosyl.