71002-88-5

Usage

Uses

Given the limited information available, it is challenging to definitively list the uses of 4-(5-Nitro-H-benzimidazol-2-yl)aniline. However, based on the presence of the benzimidazole ring and the functional groups, it can be speculated that 4-(5-nitro-H-benzimidazol-2-yl)aniline may have applications in the following areas:
Used in Pharmaceutical Industry:
4-(5-Nitro-H-benzimidazol-2-yl)aniline could be used as a starting material or intermediate in the synthesis of pharmaceutical drugs, given the prevalence of benzimidazole in therapeutic agents. The nitro and aniline groups may allow for further chemical modifications to enhance the compound's therapeutic properties.
Used in Chemical Research:
As a complex chemical compound, 4-(5-Nitro-H-benzimidazol-2-yl)aniline may serve as a subject of study in chemical research, particularly in the fields of organic synthesis and medicinal chemistry. Its reactivity and potential to undergo various chemical reactions could be of interest to researchers exploring new synthetic pathways or drug discovery.

InChI:InChI=1/C13H10N4O2/c14-9-3-1-8(2-4-9)13-15-11-6-5-10(17(18)19)7-12(11)16-13/h1-7H,14H2,(H,15,16)

Upstream product

• 2963-77-1 4-(1H-benzimidazol-2-yl)aniline 
• 150-13-0 4-amino-benzoic acid 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 556-18-3 4-aminobenzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 122-85-0 para-acetamidobenzaldehyde 
• 745809-88-5 2-(4-p-acetaminophenyl)-5⁽⁶⁾-nitrobenzimidazole 
• 1772-39-0 6-nitro-2-(4-nitrophenyl)-1H-benzo[d]imidazole 

Downstream Products

• 87345-59-3 5-Nitro-4'-trifluoroacetamido-2-phenylbenzimidazole 
• 345934-83-0 N-[4-(6-Amino-1H-benzoimidazol-2-yl)-phenyl]-2,2,2-trifluoro-acetamide 
• 87345-65-1 N,N'-Bis<2-(4-aminophenyl)benzimidazol-5-yl>terephthaloyl diamide 
• 87353-68-2 N,N'-Bis<2-(4-trifluoroacetamidophenyl)benzimidazol-5-yl>terephthaloyl diamide 
• 1027223-34-2 N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-2-thiophen-2-yl-acetamide 
• 1026492-55-6 4-fluoro-N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 
• 1026869-56-6 3-chloro-N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 
• 911211-59-1 2-chloro-N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 
• 1027223-35-3 4-cyano-N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 
• 1027233-87-9 N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-4-trifluoromethyl-benzamide 
• 1025982-82-4 3,4,5-trimethoxy-N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 
• 1026280-35-2 cyclopropanecarboxylic acid [4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-amide 
• 1025894-45-4 N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 
• 1027202-86-3 4-methyl-N-[4-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-benzamide 

Relevant academic research and scientific papers

Experimental and theoretical investigation of long-wavelength fluorescence emission in push-pull benzazoles: Intramolecular proton transfer or charge transfer in the excited state?

This study presents the synthesis, characterisation and theoretical calculations of compounds that contain electron donor and withdrawing groups connected through a π-conjugated benzazolic structure. The compounds in solution show an absorption maximum in the UV-visible spectrum (380-390 nm) due to spin and symmetry allowed electronic 1ππ? transitions with no clear evidence for charge transfer in either compound in the ground state. A fluorescence emission located in the violet-blue-green region, tailored by solvent polarity, with a large Stokes shift was observed. Taking the long-wavelength emission into account, the Lippert-Mataga plot indicates a positive solvatochromism in the solvent polarity function (Δf) range 0.02-0.20, related to the occurrence of an ICT mechanism in the excited state. At Δf greater than 0.20, the polarity of the medium seems no longer to increase the stabilization of the compounds, reaching a plateau. Time-dependent density functional theory (TD-DFT) and resolution-of-identity second-order approximate coupled-cluster (RI-CC2) calculations were also used to better understand the excited state of these compounds. The results indicated that ESIPT was disfavoured in the compounds, mainly in polar solvents, and the emission wavelengths were primarily associated with ICT. In summary, in these push-pull compounds, the electron donating and withdrawing groups do not favour the ESIPT process.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

BENZIMIDAZOLE DERIVATIVES FOR DNA METHYLATION INHIBITORS

The invention provides for DNA methylation inhibitors, and also methods and use of the compounds of the invention, by themselves or in combination with other therapies, for treating a disease in which DNA hypermethylation is found.

Structure-guided design and development of novel benzimidazole class of compounds targeting DNA gyraseB enzyme of Staphylococcus aureus

The gyraseB subunit of Staphylococcus aureus DNA gyrase is a well-established and validated target though less explored for the development of novel antimicrobial agents. Starting from the available structural information in PDB (3TTZ), we identified a novel series of benzimidazole used as inhibitors of DNA gyraseB with low micromolar inhibitory activity by employing structure-based drug design strategy. Subsequently, this chemical class of DNA gyrase inhibitors was extensively investigated biologically through in vitro assays, biofilm inhibition assays, cytotoxicity, and in vivo studies. The binding affinity of the most potent inhibitor 10 was further ascertained biophysically through differential scanning fluorimetry. Further, the most potent analogues did not show any signs of cardiotoxicity in Zebra fish ether-a-go-go-related gene (zERG), a major breakthrough among the previously reported cardiotoxic gyraseB inhibitors.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

Identification of potent agonists of photoreceptor-specific nuclear receptor (NR2E3) and preparation of a radioligand

Agonists of NR2E3 (PNR, RNR) have been identified and optimized to EC50 200 nM. A tritiated analogue of one agonist was prepared to aid in the development of a binding assay.

Substituted 2-phenyl-benzimidazole derivatives: novel compounds that suppress key markers of allergy

The pharmacotherapy of allergy and asthma has traditionally focused on the effecter molecules of the allergic cascade, while neglecting targets that play an early role in their development. Reasoning that IgE is central to the expansion of atopic diseases, we identified and extended a novel family of 2-(substituted phenyl)-benzimidazole inhibitors of IgE response. Pharmacological activity depends on an intact phenylbenzimidazole-bis-amide backbone, and is optimized by the presence of lipophilic terminal groups composed of either bis cycloalkyl or combinations of aliphatic and halogen-substituted aromatic groups. These compounds also inhibit IL-4 and IL-5 responses in T cells and CD23 expression on B cells, with potencies that parallel their inhibition of IgE. The broad profile of these compounds thus underscores their potential for treating the multifarious pathology of asthma.

Tuning second-order optical nonlinearities in push-pull benzimidazoles

The synthesis and full characterization of new chromophores with second order optical nonlinearities containing the 2-phenyl-(5,6)-nitrobenzimidazole group is reported. Starting from 2-{4-[(4-N,N-dihydroxyethylamino)phenylazo] phenyl}-5(6)-nitrobenzimidazole, a combined theoretical and experimental approach, including theoretical computations of second order nonlinear optical activity (MNDO/AM1), X-ray structural analysis and synthetic strategies, has led to a significant optimization (more than 50%) of the NLO activity of related chromophores. The results indicate that 6-nitro-substituted compounds are more active than 5-nitro-substituted ones and that a further increase of NLO activity can be achieved by insertion of a carbon-carbon double bond between the benzimidazole and 2-phenyl rings. Calculations also suggest that an additional improvement of the nonlinearity should be expected upon functionalization of the N1 atom of the 6-nitrobenzimidazole with electron-withdrawing groups. Experimental nonlinearities (EFISH technique, μβ/ 10-48 esu, γ = 1.907 μm, DMF solution) between 940 and 1550 were measured. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

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 SYMMETRICAL TEREPHTHALOYL DERIVATIVES OF 2-(p-AMINOPHENYL)-5-AMINOBENZIMIDAZOLES - MONOMERS FOR THE PREPARATION OF POLYAMIDES

Various methods for the synthesis of symetrical terephthaloyl derivatives of 2-(p-aminophenyl)-5-aminobenzimidazoles were studied.Acylation of the isomeric aminonitro-2-phenylbenzimidazoles obtained in this research with subsequent reduction of the nitro groups was found to be the most preparatively convenient method.