145861-59-2

Usage

Uses

Used in Pharmaceutical Industry:
5-NITRO-2-(3-PYRIDINYL)-1H-BENZIMIDAZOLE is used as an antibiotic for its antimicrobial properties, which are attributed to the nitro group's ability to disrupt essential cellular processes in microorganisms, thereby inhibiting the growth of certain bacteria.
Used in Antiparasitic Applications:
In the field of antiparasitic treatment, 5-NITRO-2-(3-PYRIDINYL)-1H-BENZIMIDAZOLE is utilized as an anti-parasitic agent, showing promising results in research for inhibiting the growth of specific parasites, thus offering a potential solution for combating parasitic infections.

InChI:InChI=1/C12H8N4O2/c17-16(18)9-3-4-10-11(6-9)15-12(14-10)8-2-1-5-13-7-8/h1-7H,(H,14,15)

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 59-67-6 nicotinic acid 
• 1121-60-4 pyridine-2-carbaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 1137-67-3 2-(3-pyridyl)-1H-benzimidazole 

Downstream Products

• 1571-99-9 5-amino-2-(β-pyridyl)benzimidazoles 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of some novel benzimidazole derivatives for their potential anticonvulsant activity

Selective GABAA receptor ligands are widely used clinically to reduce the occurrence of convulsions. Hence there is an intense interest in developing new benzimidazole derivatives demonstrating high selectivity and high affinity for GABAA

Synthesis of pyridinyl-benzo[d]imidazole/pyridinyl-benzo[d]thiazole derivatives and their yeast glucose uptake activity in vitro

Background: Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity. Methods: In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals. Results: Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 μM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) showed an excellent yeast glucose uptake activity better than the standard. Conclusion: Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.

Synthesis and evaluation of novel bacterial rRNA-binding benzimidazoles by mass spectrometry

A series of novel benzimidazoles were efficiently synthesized using both solution- and solid-phase chemistry. These compounds were found to bind to the bacterial 16S ribosomal RNA A-site with micromolar affinities using unique mass spectrometry-based assays.

Synthesis of 2-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)benzimidazoles

A useful approach for the synthesis of pharmacologically active tetrahydropyridinylbenzimidazoles is described. 2-Pyridin-3-ylbenzimidazoles 3a-d have been synthesized by condensation of 3-pyridinecarboxaldehyde 1 with substituted 1,2-phenylenediamines 2a-d following oxidative cyclization with iodobenzene diacetate. Methylation of 3a-d with iodomethane and potassium hydroxide, subsequent formation of methylpyridinium salts 4a-d and 7a-d and reduction thereafter afforded tetrahydropyridinylbenzimidazoles 5a-d and 8a-d.

Chemistry of 2-substituted benzimidazoles. 1. 5-Amino-2-methyl(aryl, arylalkyl, pyridyl)benzimidazoles

A series of 2-substituted benzimidazoles was synthesized. These products were consecutively converted into 5-nitro- and 5-amino-2-substituted benzimidazoles.