6232-92-4

Basic information

• Product Name: 2-AMINO-5-NITRO-1H-BENZIMIDAZOLE
• Synonyms: 2-AMINO-6-NITROBENZIMIDAZOLE;2-AMINO-5-NITRO-1H-BENZIMIDAZOLE;1H-Benzimidazol-2-amine,5-nitro-(9CI);2-Amino-5-nitro-benzimidazole;2-amine-5-nitro-1H-benzimidazole;2-Amino-5-nitro-1H-benzimidazole ,98%;5-Nitro-1H-benzo[d]imidazol-2-amine;6-Nitro-1H-benzo[d]iMidazol-2-aMine
• CAS NO: 6232-92-4
• Molecular Formula: C₇H₆N₄O₂
• Molecular Weight: 178.15
• Product Categories: BENZIMIDAZOLE;pharmacetical;Imidazol&Benzimidazole
• Mol File: 6232-92-4.mol

Chemical Properties

• Melting Point: 222-223 °C (decomp)
• Boiling Point: 478.5 °C at 760 mmHg
• Flash Point: 243.2 °C
• Appearance: /
• Density: 1.631 g/cm³
• Vapor Pressure: 2.55E-09mmHg at 25°C
• Refractive Index: 1.816
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.63±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-NITRO-1H-BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-NITRO-1H-BENZIMIDAZOLE(6232-92-4)
• EPA Substance Registry System: 2-AMINO-5-NITRO-1H-BENZIMIDAZOLE(6232-92-4)

Safety Data

• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 6232-92-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-NITRO-1H-BENZIMIDAZOLE is used as a starting material for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or diseases.
Used in Dye Industry:
In the dye industry, 2-AMINO-5-NITRO-1H-BENZIMIDAZOLE is utilized for the production of dyes. Its chemical properties contribute to the color and stability of the dyes, making it a valuable component in the formulation of various colorants.
Used in Organic Chemistry Research:
2-AMINO-5-NITRO-1H-BENZIMIDAZOLE is used as a research compound in organic chemistry. Its reactivity and structural features make it an interesting subject for studies aimed at understanding chemical reactions and developing new synthetic methods.
Used in Antimicrobial Applications:
2-AMINO-5-NITRO-1H-BENZIMIDAZOLE has been studied for its potential antimicrobial properties. It is used in research to explore its effectiveness against various microorganisms, which could lead to the development of new antimicrobial agents.
Used in Material Science:
In material science, 2-AMINO-5-NITRO-1H-BENZIMIDAZOLE may be used to develop new materials with specific properties. Its chemical structure could contribute to the creation of materials with unique electronic, optical, or mechanical characteristics.

InChI:InChI=1/C7H6N4O2/c8-7-9-5-2-1-4(11(12)13)3-6(5)10-7/h1-3H,(H3,8,9,10)

Upstream product

• 934-32-7 1H-benzimidazol-2-amine 
• 5955-72-6 2-chloro-5-nitro-1H-benzo[d]imidazole 
• 506-68-3 bromocyane 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 75966-22-2 2,4-Dinitrophenylcyanamid 
• 1184-90-3 aminoiminomethanesulfonic acid 
• 6325-91-3 5-nitro-2-mercaptobenzimidazole 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 557-21-1 zinc(II) cyanide 
• 100-01-6 4-nitro-aniline 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 610-53-7 2,4-dinitroacetanilide 
• 97-02-9 2,4-Dinitroanilin 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 20559-51-7 N-(5-nitro-1H-benzimidazol-2-yl)benzamide 
• 1215352-95-6 (E)-N-(2-amino-1H-benzo[d]imidazol-5-yl)-4-(1-(2-methyl-3-phenylallyl)-1H-1,2,3-triazol-4-yl)butanamide hydrochloride 
• 1215353-04-0 N-(2-amino-1H-benzo[d]imidazol-5-yl)-4-(4-decyl-1H-1,2,3-triazol-1-yl)benzamide hydrochloride 
• 1215352-90-1 4-(4-(4-(2-amino-1H-benzo[d]imidazol-5-ylamino)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)benzoic acid hydrochloride 
• 1215351-97-5 tert-butyl 5-(4-azidobenzamido)-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate 
• 1215351-99-7 tert-butyl 6-(4-azidobenzamido)-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate 
• 1215353-01-7 N-(2-amino-1H-benzo[d]imidazol-5-yl)-4-(4-butyl-1H-1,2,3-triazol-1-yl)benzamide hydrochloride 
• 1215353-17-5 N-(2-amino-1H-benzo[d]imidazol-5-yl)-2-fluorobenzenesulfonamide hydrochloride 

Relevant articles and documents

Benzimidazole scaffold based hybrid molecules for various inflammatory targets: Synthesis and evaluation

Designing of hybrid drugs with specific multitarget profile is a promising line of attack against inflammation. In light of this, a series of benzimidazole scaffold based hybrid molecules were designed by integrating benzimidazoles (containing pharmacophoric elements for COXs and LOXs inhibitors) with phthalimide subunit of thalidomide (pharmacophore element for TNF-α inhibitor) under one construct via molecular hybridization strategy. The designed molecules were synthesized and evaluated for their inhibitory activity against COXs (COX-1, COX-2), LOXs (5-LOX, 15-LOX) enzymes as well as TNF-α inhibitory effect. The results revealed that, compounds (3a–l) obtained showed inhibition in submicromolar range against COXs and LOXs targets whereas milder inhibitory activity was obtained against lipopolysaccharides (LPS)-induced TNF-α secretion by murine macrophage-like cells (RAW264.7). Within this class of compounds, 3j emerged as having alluring multiple inhibitory effects on set of COX-1/2 and 5-/15-LOX enzymes (COX-1 IC50 = 9.85 μM; COX-2 IC50 = 1.00 μM; SI = 9.85; 5-LOX IC50 = 0.32 μM; 15-LOX IC50 = 1.02 μM) in conjunction with a good anti-inflammatory and analgesic activities. Additionally, compound 3j showed gastrointestinal safety with reduced lipid peroxidation. Docking results of compound 3j with COX-2 and 5-LOX were also consistent with the in vivo anti-inflammatory results.

Design, synthesis and biological evaluation of 2-(2-amino-5(6)-nitro-1H-benzimidazol-1-yl)-narylacetamides as antiprotozoal agents

Parasitic diseases are a public health problem affecting millions of people worldwide. One of the scaffolds used in several drugs for the treatment of parasitic diseases is the benzimidazole moiety, a heterocyclic aromatic compound. This compound is a crucial pharmacophore group and is considered a privileged structure in medicinal chemistry. In this study, the benzimidazole core served as a model for the synthesis of a series of 2-(2-amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides 1-8 as benznidazole analogues. The in silico pharmacological results calculated with PASS platform exhibited chemical structures highly similar to known antiprotozoal drugs. Compounds 1-8 when evaluated in silico for acute toxicity by oral dosing, were less toxic than benznidazole. The synthesis of compounds 1-8 were carried out through reaction of 5(6)-nitro- 1H-benzimidazol-2-amine (12) with 2-chlroactemides 10a-h, in the presence of K2CO3 and acetonitrile as solvent, showing an inseparable mixture of two regioisomers with the -NO2 group in position 5 or 6 with chemical yields of 60 to 94%. The prediction of the NMR spectra of molecule 1 coincided with the experimental chemical displacements of the regioisomers. Comparisons between the NMR prediction and the experimental data revealed that the regioisomer endo-1,6-NO2 predominated in the reaction. The in vitro antiparasitic activity of these compounds on intestinal unicellular parasites (Giardia intestinalis and Entamoeba histolytica) and a urogenital tract parasite (Trichomonas vaginalis) were tested. Compound 7 showed an IC50 of 3.95 μM and was 7 time more active against G. intestinalis than benznidazole. Compounds 7 and 8 showed 4 times more activity against T. vaginalis compared with benznidazole.

Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines

An operationally simple oxidation-cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.

1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation

Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.

INDOLE DERIVATIVE, PREPARATION METHOD THEREOF, AND USE THEREOF IN PHARMACEUTICAL DRUG

An indole derivative as expressed by Formula (I), a preparation method thereof, a pharmaceutical salt, and use thereof as a therapeutic agent, especially as a FGFR inhibitor. Each substituent in Formula (I) has identical definition as specified in the specification.

COMPOUNDS AND METHODS FOR TREATMENT OF CANCER BY INHIBITING ATG4B AND BLOCKING AUTOPHAGY

ATG4B inhibitor compounds, compositions that include the compounds, and methods for using the compounds and compositions in the treatment of cancer by inhibiting ATG4B and/or blocking autophagy.

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Copper-Catalyzed C NH2Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles

A copper(II)-catalyzed selective C NH2arylation of 2-aminobenzimidazoles and related C-amino-NH-azoles was achieved in presence of 2,2′-bipyridine and cesium carbonate at 60 °C under open air conditions and this is first method for the copper-catalyzed selective C NH2arylation in the presence of other reactive nucleophilic sites. Previously unexplored heteroaromatics possessing multiple nucleophilic sites that are selectively arylated at the C NH2position are obtained, providing an exceptional tool for rapid delivery of a diverse array of medicinally important C NH(aryl) derivatives of aminoazoles without any protection/deprotection of ring N H bonds. It is first example for the selective C NH2arylation of 5-aminoindazole, 4-aminopyrazole, 5-aminopyrazole, 9H-purine-6-amine, and 1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives. (Figure presented.) .

Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles

Two groups of benzimidazole derivatives were synthesized using as precursors 5(6)-substituted 2-mercapto-benzimidazol-thiols and their antioxidant activity was investigated using TBA-MDA test. In the group of 1,3-disubstituted-benzimidazol-2-imines the highest lipid peroxidation inhibition effect 74.04% (IC50 = 141.89 μg/mL) revealed ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimdazol-1-yl]acetate 12 while in the group of 2-substituted-1,3-thiazolo[3,2-a]benzimidazolones the highest inhibition effect showed 2-(4-fluorobenzylidene)-7-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 17 90.76% (IC50 = 53.70 μg/mL). In order to estimate the capability of the studied benzimidazoles to act as radical scavengers the structure of the most active derivative within the both subseries was optimized at B3LYP/6-311++G?? level and the respective bond dissociation enthalpies were calculated. The appropriate models for the HAT and SET-mechanism of the antioxidant activity were proposed. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and three Gram-negative bacteria (Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027 and Salmonella abony NCTC 6017). 1,3-Diphenylpropyl-5-methyl-1,3-dihydro-2H-benzimidazol-2-imine 14 exhibited significant activity against B. subtilis, S. aureus, S. abony and E. coli (with MIC values of 0.125, 0.016, 0.50 and 0.50 mg/mL, respectively). The group of thiazolobenzimidazolones did not reveal antibacterial activity against the tested strains.

A facile synthesis of 2-aminobenzoxazoles and 2-aminobenzimidazoles using N -cyano- N -phenyl- P -toluenesulfonamide (NCTS) as an efficient electrophilic cyanating agent

A facile synthesis of 2-aminobenzoxazole and 2-aminobenzimidazole derivatives employing a nonhazardous electrophilic cyanating agent: N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) with various substituted 2-aminophenols and benzene-1,2-diamine derivatives in the presence of lithium hexamethyldisilazide (LiHMDS) is described. This novel protocol boasts operational simplicity, shorter reaction time, and simple workup.