3156-18-1

Usage

Chemical structure

A benzimidazole derivative with a chlorine atom and a phenoxymethyl group attached to the benzene ring

Usage

Building block in the synthesis of various bioactive molecules in the pharmaceutical industry

Pharmacological activities

Antiviral, antifungal, anticancer, and anti-inflammatory properties

Specific properties and potential applications

Not widely studied, but may have potential as a drug candidate or as a precursor in organic synthesis due to its structural features.

Upstream product

• 122-88-3 4-Chlorophenoxyacetic acid 
• 95-54-5 1,2-diamino-benzene 
• 79397-26-5 N-(p-chlorophenoxyacetyl)phenylalanine methyl ester 
• 106-48-9 4-chloro-phenol 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 3598-13-8 (4-chlorophenoxy)acetonitrile 
• 615-28-1 o-phenylenediamine dihydrochloride 

Downstream Products

• 210564-62-8 4-{2-[2-(4-Chloro-phenoxymethyl)-benzoimidazol-1-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 193626-31-2 4-{3-[2-(4-Chloro-phenoxymethyl)-benzoimidazol-1-yl]-propyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 210564-57-1 2-{2-[2-(4-Chloro-phenoxymethyl)-benzoimidazol-1-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 750599-05-4 2-(4-chlorophenoxymethyl)-1H-benzimidazole acetic acid hydrazide 
• 1403579-55-4 C₁₇H₁₄ClN₄O₂S₂^(1-)*K⁽¹⁺⁾ 
• 1257231-31-4 4-amino-5-[2-(4-chlorophenoxymethylbenzimidazole)-1-methylene]-3-mercapto-1,2,4-triazole 
• 1227751-28-1 C₂₄H₁₇ClN₆OS 
• 1227751-29-2 C₂₅H₁₉ClN₆OS 
• 1227751-30-5 C₂₅H₁₉ClN₆OS 
• 1227751-31-6 C₂₅H₁₉ClN₆OS 
• 1227751-32-7 C₂₅H₁₉ClN₆O₂S 
• 1227751-33-8 C₂₅H₁₉ClN₆O₂S 
• 1227751-34-9 C₂₅H₁₉ClN₆O₂S 
• 1227751-35-0 C₂₄H₁₆Cl₂N₆OS 

Relevant academic research and scientific papers

1-ethyl gallate-2-substituted phenoxymethyl benzimidazoles: Synthesis, molecular structure, antimicrobial activities and complex with Cr(III)

Summary: The design of gallate and benzimidazole containing derivatives is expected to produce new bioactive molecules with multiple applications. Here the synthesis of eight novel benzimidazole compounds containing ethyl gallate and substituted phenoxyme

Synthesis and molecular structures of 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles

Five novel 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles were synthesized by a three-step route. Under microwave irradiation, the p-substituted phenols were firstly O-carboxymethylated to prepare the corresponding p-substituted phenoxymethyl acids, which then reacted with o-phenylendiamine to get the key intermediates 2-(p-substituted) phenoxymethyl benzimidazole. Finally, the solid-liquid phase transfer catalysis method, where tetrabutyl ammonium bromide (TBAB) was used as the catalyst, was applied to synthesize the target compounds c1-c5 by the N-hydroxyethylation reaction with 2-chloroethyl alcohol. The structures of the obtained compounds were well characterized and confirmed by elemental analysis, MS, IR, 1H NMR, 13C NMR and single-crystal X-ray diffraction analysis.

BENZIMIDAZOLE DERIVATIVES AS SELECTIVE BLOCKERS OF PERSISTENT SODIUM CURRENT

The present invention is directed to a compound of Formula (I) or a pharmaceutically acceptable salt thereof; wherein R, R1, R2, R3, R4, m, and n are as defined herein, to pharmaceutical compositions comprising said compound, and to methods of treating diseases or conditions mediated by elevated persistent sodium current, such as an ocular disorder, multiple sclerosis, seizure disorder, and chronic pain.

Aza-Michael addition of acrylonitrile with 2-aryloxymethylbenzimidazole derivatives under microwave irradiation

A simple, rapid, and highly efficient method has been developed for the aza-Michael addition of acrylonitrile to 2-aryl-oxymethylbenzimidazole derivatives in the presence of anhydrous potassium carbonate under microwave irradiation. A series novel of 1-cyanoethyl-2-aryloxymethylbenzimidazole derivatives have been prepared and characterised by 1H NMR, 13C NMR, IR spectra and elemental analysis.

Synthesis and bioactivity of a novel series of 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles

A novel series of 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4- thiadiazoles were synthesized by the condensation of 4-amino-5-[2-(4- chlorophenoxymethylbenzimidazole)-1-methylene]-3-mercapto-1,2,4-triazole with various (un)substituted aromatic acids in the presence of phosphorous oxychloride. These compounds were investigated for their inhibitory activity to E. coli methionine aminopeptidase (EcMetAP1). Some of the tested compounds showed significant inhibitory activity.

Discovery of some benzimidazole derivatives as a new agrochemical fungicides

VARIOUSLY new substituted benzimidazole derivatives were synthesized with a wide range of suhstitucnis. Compounds were prepared by the reaction of 2-chloromethylbenzimidazole with different nitrogen, oxygen and sulfur nucleophiles as well as acetylacetone as an active methylene containing compound in organic solvent in the presence of hydrogen chloride acceptor. Most of the synthesized compounds were assayed for their fungicidal activity on three soil borne fungi. Some of the new synthesized compounds showed higher fungicidal activity than the standard fungicide Penycvcuron (Moncerene 25% WP).

Synthesis and structure-activity relationships of new antimicrobial active multisubstituted benzazole derivatives

A series of multisubstituted benzoxazoles, benzimidazoles, and benzothiazoles (5-7) as non-nucleoside fused isosteric heterocyclic compounds was synthesized and tested for their antibacterial activities against various Gram-positive and Gram-negative bacteria and antifungal activity against the fungus Candida albicans. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 100 and 3.12 μg/ml. Structure-activity relationships (SAR) studies revealed that benzothiazole ring system enhanced the antimicrobial activity against Staphylococcus aureus. In these sets of non-nucleoside fused heterocyclic compounds electron withdrawing groups at position 5 of the benzazoles increased the activity against C. albicans.

Synthesis and evaluation of a series of novel 2-[(4- chlorophenoxy)methyl]benzimidazoles as selective neuropeptide Y Y1 receptor antagonists

A series of novel benzimidazoles (BI) derived from the indole 2 was synthesized and evaluated as selective neuropeptide Y (NPY) Y1 receptor antagonists with the aim of developing antiobesity drugs. In our SAR approach, the (4-chlorophenoxy)methyl group at

Inhibition of Rat Hepatic Microsomal Aminopyrine N-Demethylase Activity by Benzimidazole Derivatives. Quantitative Structure-Activity Relationships

Eighty-two benzimidazole derivatives have been prepared and tested for the ability to inhibit cytochrome P-450 mediated enzyme activity (aminopyrine N-demethylase) from phenobarbitone-induced rat hepatic microsomes.Using physicochemical parameters and multiple regression analysis, we derived a quantitative structure-activity relationship (QSAR) that describes up to 87percent of the data variance in terms of hydrophobic and electronic effects and the molar refractivity of the substituent in the 2-position of the benzimidazole ring.