69570-99-6

Basic information

• Product Name: 2-(4-NITRO-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID
• Synonyms: 2-(4-NITRO-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID;2-(4-Nitrophenyl)-1H-benzimidazole-5-carboxylic acid;2-(4-nitrophenyl)-1H-1,3-benzodiazole-6-carboxylic acid
• CAS NO: 69570-99-6
• Molecular Formula: C₁₄H₉N₃O₄
• Molecular Weight: 283.24
• Mol File: 69570-99-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 609.785°C at 760 mmHg
• Flash Point: 322.586°C
• Appearance: /
• Density: 1.533g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: 2-(4-NITRO-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-NITRO-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(69570-99-6)
• EPA Substance Registry System: 2-(4-NITRO-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(69570-99-6)

Safety Data

• Hazardous Substances Data: 69570-99-6(Hazardous Substances Data)

Usage

Molecular Structure

2-(4-Nitro-phenyl)-3H-benzoimidazole-5-carboxylic acid is a heterocyclic compound that contains a benzimidazole ring with a carboxylic acid group and a nitrophenyl substitution.

Biological Activities

The compound has diverse biological activities, including antimicrobial, antitumor, and anti-inflammatory properties.

Functional Groups

The nitro group in the molecule is responsible for its antimicrobial activity, while the benzimidazole ring is associated with its antitumor and anti-inflammatory effects.

Applications

The compound is commonly used as a building block in the synthesis of pharmaceutical compounds and has potential applications in drug discovery and development due to its versatile pharmacological properties.

InChI:InChI=1/C14H9N3O4/c18-14(19)9-3-6-11-12(7-9)16-13(15-11)8-1-4-10(5-2-8)17(20)21/h1-7H,(H,15,16)(H,18,19)

Upstream product

• 41468-11-5 sodium hydroxy(4-nitrophenyl)methanesulfonate 
• 619-05-6 3,4-diaminobenzoic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 69570-96-3 methyl 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylate 

Downstream Products

• 820242-64-6 2-(4-nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid adamantan-1-ylamide 
• 459809-23-5 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylic acid pyridin-2-yl-amide 
• 190121-99-4 2-(4-aminophenyl)benzimidazole-5-carboxylic acid 
• 69570-96-3 methyl 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylate 

Relevant articles and documents

Design, synthesis, mechanistic studies and in silico ADME predictions of benzimidazole derivatives as novel antifungal agents

Herein, novel three series of benzimidazole scaffold bearing hydrazone, 1,2,4-triazole and 1,3,4-oxadiazole moieties 1-3, 4a-j, 6a-c and 7 derivatives were designed, synthesized and evaluated for their antimicrobial activity. The structures of the prepared compounds were assigned using different spectroscopic techniques such as IR, 1H NMR, 13C NMR and elemental analyses. Compounds 3, 4a, 4e and 4f exhibited remarkable antifungal activity against C. albicans and C. neoformans var. grubii with MIC values ranging from 4 to 16 μg/mL. Furthermore, they were not cytotoxic against red blood cells and human embryonic kidney cells at concentration up to 32 μg/mL. The study was expanded to forecast the mechanism of action of the prepared compounds and determine sterol quantitation method (SQM) by spectrophotometric assay. On the other hand, compound 4e showed the highest inhibitory activity against lanosterol 14α-demethylase (CYP51) with IC50 value = 0.19 μg/mL compared to fluconazole as reference IC50 value = 0.62 μg/mL. Also, compounds 4d and 4f exhibited mild to moderate antibacterial activity. Moreover, molecular docking of the active target compound 4e in active site of lanosterol 14α-demethylase (CYP51) revealed that docking scores and binding mode are comparable to that of co-crystallized ligand confirming their antifungal activity. In silico ADME prediction investigations also forecasting the drug-like characters of these compounds.

Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

Novel 4″-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4″ bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the mef gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4″-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4″-O-(2-alkyl)benzimidazolyl derivatives.

Very fast and efficient synthesis of some novel substituted 2-arylbenzimidazoles in water using ZrOCl2?nH2O on montmorillonite K10 as catalyst

A simple and eco-friendly protocol for the synthesis of some novel substituted 2-arylbenzimidazoles was developed. In this process, these compounds were prepared in water as the solvent using ZrOCl2?nH 2O supported on montmorillonite K10 as an efficient water tolerating Lewis acid. The reaction was performed under mild conditions with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct.