6637-29-2

Usage

Uses

Used in Gastroenterology:
2-(phenoxymethyl)-1H-benzimidazole hydrochloride is used as an anti-ulcer agent for its ability to inhibit gastric acid secretion and promote healing of damaged gastrointestinal mucosa. This makes it particularly effective in the treatment of peptic ulcers and gastroesophageal reflux disease, as well as other gastric and duodenal disorders, showcasing its therapeutic potential in the field of gastroenterology.

InChI:InChI=1/C14H12N2O/c1-2-6-11(7-3-1)17-10-14-15-12-8-4-5-9-13(12)16-14/h1-9H,10H2,(H,15,16)

Upstream product

• 40828-54-4 1H-benzimidazole-2-sulfonic acid 
• 122-59-8 2-phenoxyacetic acid 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 1039358-73-0 C₂₁H₂₅ClN₂O 
• 1039358-74-1 C₂₂H₂₇ClN₂O 
• 1039358-75-2 C₂₃H₂₉ClN₂O 
• 1039358-71-8 C₁₉H₂₁ClN₂O 
• 1039358-76-3 C₂₄H₃₁ClN₂O 
• 92756-20-2 C₂₁H₁₆N₂O₂ 
• 1039358-69-4 C₁₇H₁₇ClN₂O 
• 439574-26-2 C₂₁H₁₈N₂O₃S 
• 1039358-70-7 C₁₈H₁₉ClN₂O 
• 1039358-72-9 C₂₀H₂₃ClN₂O 
• 112055-57-9 C₁₇H₁₅N₃O 

Relevant academic research and scientific papers

Quantum mechanical and spectroscopic (FT-IR, FT-Raman, 1H NMR and UV) investigations of 2-(phenoxymethyl)benzimidazole

The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 2-(phenoxymethyl)benzimidazole have been investigated experimentally and theoretically using Gaussian09 software package. The energy and oscillator streng

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.

Synthesis, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline

2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-{5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10-5 M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).

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.

A rapid and convenient synthesis of derivatives of imidazoles under Microwaveirradiation

Anefficient and a quick microwave-assisted synthesis of benzimidazoles and trisubstituted imidazoles was developed. Three benzimidazoles were obtained as a result of the condensation of 1,2-phenylenediamine with carboxylic acids and acetoacetic ester without catalyst. A series of trisubstituted imidazoles were syn thesized by condensation of benzil, aromatical dehyde and ammonium acetate in the presence of glacial acetic acid.

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 HIV-1 reverse transcriptase inhibitor activity of some 2,5,6-substituted benzoxazole, benzimidazole, benzothiazole and oxazolo (4,5-b)pyridine derivatives

In this study, the synthesis of some benzoxazoles and their analogues were described and their antiviral activities were studied together with the previously synthesized 2,5,6-trisubstituted benzoxazole, benzothiazole, benzimidazole and oxazolo(4,5-b)pyridine derivatives. The reverse transcriptase (RT) inhibitory activity of these compounds was determined using a commercial kit and assay system which utilizes the scintillation proximity assay principle. The results are concentration at which the compound inhibits RT activity by 50%). The compounds inhibited the in vitro binding of thymidine to the RT enzyme exhibiting IC50 values between 6.3 × 105 μmol/l-0.34 μmol/l and their activities were compared to some standard drugs such as 3′-azido-2′,3′-dideoxythymidine triphosphate and dideoxythymidine triphosphate.