148533-73-7

Basic information

• Product Name: 5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE
• Synonyms: ASISCHEM D50988;AKOS BB-7919;5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE;5-NITRO-2-(4-PYRIDYL)BENZIMIDAZOLE;5-NITRO-2-PYRIDIN-4-YL-1H-BENZIMIDAZOLE;TIMTEC-BB SBB000793;ZERENEX E/6023014;5-Nitro-2-(pyridin-4-yl)-1H-benzo[d]iMidazole
• CAS NO: 148533-73-7
• Molecular Formula: C12H8N4O2
• Molecular Weight: 240.22
• Mol File: 148533-73-7.mol

Chemical Properties

• Melting Point: 224-226 °C
• Boiling Point: 527.1 °C at 760 mmHg
• Flash Point: 272.6 °C
• Appearance: /
• Density: 1.451 g/cm³
• Vapor Pressure: 3.37E-11mmHg at 25°C
• Refractive Index: 1.727
• Storage Temp.: 2-8°C
• PKA: 8.27±0.10(Predicted)
• CAS DataBase Reference: 5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE(148533-73-7)
• EPA Substance Registry System: 5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE(148533-73-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 148533-73-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE is used as an antiprotozoal drug for the treatment of Chagas disease, a parasitic infection caused by Trypanosoma cruzi. It is effective in producing nitro radicals that interact with the parasite's macromolecules, leading to cell death and alleviating the symptoms of the disease.
Used in Treatment of Other Protozoal Infections:
5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE is also used as a therapeutic agent for other protozoal infections such as leishmaniasis and giardiasis. Its ability to generate nitro radicals and interact with the parasites' macromolecules makes it a valuable treatment option for these conditions.
Used in Research and Development:
5-NITRO-2-(4-PYRIDINYL)-1H-BENZIMIDAZOLE serves as a valuable compound in the field of research and development, particularly in the study of antiprotozoal drugs and their mechanisms of action. Its unique properties and activity against various protozoal infections make it an important subject for further investigation and potential development of new therapeutic agents.

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

Upstream product

• 2208-59-5 2-(pyridin-4-yl)-1H-benzo[d]imidazole 
• 872-85-5 pyridine-4-carbaldehyde 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 108-89-4 picoline 
• 619-18-1 2,5-dinitroaniline 
• 95-54-5 1,2-diamino-benzene 
• 55-22-1 pyridine-4-carboxylic acid 

Downstream Products

• 1434517-57-3 2-phenoxy-N-[(2-pyridin-4-yl)-1H-benzo[d]imidazole-5-yl]propionamide 
• 1724-67-0 2-(pyridin-4-yl)-1H-benzo[d]imidazole-5-amine 

Relevant articles and documents

Heterocyclic betaines. XXII. Azinium(Azolium) 4-nitrobenzimidazolate inner salts and their derivatives with several interannular spacers. Synthesis, characterization and antitrichomonal activity

The synthesis of an ensemble of pyridinium(imidazolium) 4-nitrobenzimidazolate betaines and their derivatives with several interannular linkages has been explored. Their antiprotozoal activity has also been examined.

Development of 2-(4-pyridyl)-benzimidazoles as PKN2 chemical tools to probe cancer

Kinases are signalling proteins which have proven to be successful targets for the treatment of a variety of diseases, predominantly in cancers. However, only a small proportion of kinases (50 of 0.064 μM against PKN2, with ca. 17-fold selectivity over close homologue, PKN1.

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.

COMPOUNDS AND METHODS FOR TREATING MAMMALIAN GASTROINTESTINAL MICROBIAL INFECTIONS

Disclosed are compounds and pharmaceutically acceptable salts thereof, which are useful as inhibitors of IMPDH. In certain embodiments, a compound selectively inhibits a parasitic IMPDH versus a host IMPDH. Also disclosed are pharmaceutical compositions comprising one or more compounds of the invention. Related methods of treating various parasitic and bacterial infections in mammals are disclosed. Moreover, the compounds may be used alone or in combination with other therapeutic or prophylactic agents, such as anti-virals, anti-inflammatory agents, antimicrobials and immunosuppressants.

Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase

Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5′-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD +. The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC 50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD 50 > 50 μM) against a panel of four mammalian cells lines.

Iron sulfide catalyzed redox/condensation cascade reaction between 2-amino/hydroxy nitrobenzenes and activated methyl groups: A straightforward atom economical approach to 2-hetaryl-benzimidazoles and -benzoxazoles

Iron sulfide generated in situ from elemental sulfur and iron was found to be highly efficient in catalyzing a redox/condensation cascade reaction between 2-amino/hydroxy nitrobenzenes and activated methyl groups. This method represents a straightforward and highly atom economical approach to 2-hetaryl-benzimidazoles and -benzoxazoles.

6-Nitrobenzimidazole derivatives: Potential phosphodiesterase inhibitors: Synthesis and structure-activity relationship

6-Nitrobenzimidazole derivatives (1-30) synthesized and their phosphodiesterase inhibitory activities determined. Out of thirty tested compounds, ten showed a varying degrees of phosphodiesterase inhibition with IC50 values between 1.5 ± 0.043 and 294.0 ± 16.7 μM. Compounds 30 (IC50 = 1.5 ± 0.043 μM), 1 (IC50 = 2.4 ± 0.049 μM), 11 (IC50 = 5.7 ± 0.113 μM), 13 (IC50 = 6.4 ± 0.148 μM), 14 (IC50 = 10.5 ± 0.51 μM), 9 (IC50 = 11.49 ± 0.08 μM), 3 (IC50 = 63.1 ± 1.48 μM), 10 (IC50 = 120.0 ± 4.47 μM), and 6 (IC50 = 153.2 ± 5.6 μM) showed excellent phosphodiesterase inhibitory activity, much superior to the standard EDTA (IC50 = 274 ± 0.007 μM), and thus are potential molecules for the development of a new class of phosphodiesterase inhibitors. A structure-activity relationship is evaluated. All compounds are characterized by spectroscopic parameters.

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.

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.