54998-00-4

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(3-Amino-4-nitrophenyl)morpholine is used as a key intermediate in the synthesis of pharmaceuticals, particularly for the development of anti-inflammatory and anti-cancer drugs. Its unique structure allows for the creation of novel drug candidates with potential therapeutic benefits.
Used in Anticancer Applications:
In the field of oncology, 4-(3-Amino-4-nitrophenyl)morpholine is utilized as a potential anti-cancer agent. Its chemical properties enable it to target and inhibit the growth of cancer cells, making it a valuable tool in the fight against various types of cancer.
Used in Antiparasitic and Antimicrobial Applications:
4-(3-Amino-4-nitrophenyl)morpholine has been studied for its potential antiparasitic and antimicrobial properties. Its ability to target and eliminate harmful parasites and microorganisms makes it a promising candidate for use in treatments for various infectious diseases.
Used in Antioxidant and Neuroprotective Applications:
4-(3-Amino-4-nitrophenyl)morpholine has also been investigated for its role in antioxidant and neuroprotective applications. Its potential to protect cells from oxidative stress and support neuronal health positions it as a valuable asset in the development of treatments for neurodegenerative diseases and other conditions related to oxidative stress.

InChI:InChI=1/C10H13N3O3/c11-9-7-8(1-2-10(9)13(14)15)12-3-5-16-6-4-12/h1-2,7H,3-6,11H2

Upstream product

• 110-91-8 morpholine 
• 1635-61-6 5-chloro-2-nitroaniline 
• 68-12-2 N,N-dimethyl-formamide 
• 64-17-5 ethanol 
• 555-16-8 4-nitrobenzaldehdye 
• 5228-61-5 5-bromo-2-nitroaniline 

Downstream Products

• 119421-28-2 4-morpholinobenzene-1,2-diamine 
• 897446-65-0 2-cyclohexyl-N-(5-morpholin-4-yl-2-nitrophenyl)-2-phenylacetamide 
• 949570-75-6 methyl 4-chloro-2-(5-morpholino-2-nitrophenylamino)benzoate 
• 402948-33-8 ethyl 2-(5-morpholin-4-ylbenzimidazol-2-yl)acetate 
• 1227867-14-2 6-[(2-amino-5-morpholinophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide 
• 1187383-65-8 (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 1187383-66-9 (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 1187383-55-6 7-methoxy-8-{5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl}oxy-(11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 1187383-72-7 4-{2-[4-(benzyloxy)phenyl]benzimidazol-6-yl}morpholine 
• 111861-06-4 5⁽⁶⁾-Morpholino-2-(4-nitrophenyl)benzimidazole 

Relevant academic research and scientific papers

Benzimidazole compound, preparation method thereof and application of the benzimidazole compound in preparation of ferroptosis inhibitor

The invention discloses a benzimidazole compound, a preparation method thereof and application of the benzimidazole compound in preparation of a ferroptosis inhibitor. The benzimidazole compound has a structure as shown in a formula (I) or a formula (II)

Selective hydrogenation of nitroarenes under mild conditions by the optimization of active sites in a well defined Co?NC catalyst

The catalytic hydrogenation of aromatic nitro compounds containing multiple functional groups into amino compounds with high conversion rates, selectivity, and stability under mild conditions is a great challenge. Herein, a well defined catalyst (Co?NC) is prepared through the pyrolysis of the Co-centered metal-organic framework (MOF) at the optimized temperature. The as-synthesized catalyst exhibits a high conversion rate and selectivity for the hydrogenation of 12 aromatic nitro compounds with different competing groups into desired amino compounds with hydrazine hydrate under mild conditions (80 °C, 30 min, and 1 atm). The catalyst also shows excellent stability and can be reused over 20 times without considerably losing its activity. It is found that the Co-Nx site is the main active site for catalytic hydrogenation, and the Mott-Schottky effect between the surface Co NPs and N-doped carbon can further promote the hydrogenation reaction. EXAFS, TEM, XPS, and Raman analyses confirm that cobalt nanoparticles (NPs) are properly encapsulated by the N-doped carbon matrix at the optimized temperature, and the Co species maintain a high spin state after the catalysis, which may be responsible for the high performance of Co?NC. This work demonstrates not only a highly efficient catalyst for hydrogenation under mild conditions, but also provides insight into the active sites in Co-based catalysts for hydrogenation.

Pyrazole spleen tyrosine kinase inhibitor as well as preparation method and application thereof

The invention discloses a pyrazole spleen tyrosine kinase inhibitor, a preparation method thereof, a pharmaceutical composition containing the same, and application of the pyrazole spleen tyrosine kinase inhibitor and the pharmaceutical composition in the preparation of drugs for treating Syk-mediated diseases including cancers, inflammatory diseases and the like.

Targeting G-quadruplex DNA structures in the telomere and oncogene promoter regions by benzimidazole?carbazole ligands

Recent studies support the idea that G-quadruplex structures in the promoter regions of oncogenes and telomere DNA can serve as potential therapeutic targets in the treatment of cancer. Accordingly, several different types of organic small molecules that stabilize G-quadruplex structures and inhibit telomerase activity have been discerned. Here, we describe the binding of benzimidazole-carbazole ligands to G-quadruplex structures formed in G-rich DNA sequences containing the promoter regions of human c-MYC, c-KIT1, c-KIT2, VEGF and BCL2 proto-oncogenes. The fluorescence spectroscopic data indicate that benzimidazole-carbazole ligands bind and stabilize the G-quadruplexes in the promoter region of oncogenes. The molecular docking studies provide insights into the mode and extent of binding of this class of ligands to the G-quadruplexes formed in oncogene promoters. The high stability of these G-quadruplex structures was validated by thermal denaturation and telomerase-catalyzed extension of the 3' end. Notably, benzimidazole-carbazole ligands suppress the expression of oncogenes in cancer cells in a dose-dependent manner. We anticipate that benzimidazole-carbazole ligands, by virtue of their ability to stabilize G-quadruplex structures in the promoter regions of oncogenes, might reduce the risk of cancer through the loss of function in the proteins encoded by these genes.

Heterocycle type derivative and preparing method and pharmaceutical application thereof

The invention relates to a novel heterocycle type derivative, a preparing method thereof, a medicine composition containing the derivative and application of the heterocycle type derivative as therapeutic agent, particularly an FGFR4 inhibitor. The preferable compound has a good inhibiting effect on FGFR4.

Fragment-based design, synthesis, biological evaluation, and SAR of 1H-benzo[d]imidazol-2-yl)-1H-indazol derivatives as potent PDK1 inhibitors

In this work, we describe the use of the rule of 3 fragment-based strategies from biochemical screening data of 1100 in-house, small, low molecular weight fragments. The sequential combination of in silico fragment hopping and fragment linking based on S1

Hybrid pharmacophore design and synthesis of naphthalimide-benzimidazole conjugates as potential anticancer agents

Naphthalimide-benzimidazole conjugates were prepared using two different types of spacer units; either a simple alkane chain or a substituted piperazine moiety with variable alkyl side chains. Each set of conjugates was evaluated for their in vitro antica

Design and synthesis of new benzimidazole-carbazole conjugates for the stabilization of human telomeric DNA, telomerase inhibition, and their selective action on cancer cells

Cell-permeable small molecules that enhance the stability of the G-quadruplex (G4) DNA structures are currently among the most intensively pursued ligands for inhibition of the telomerase activity. Herein we report the design and syntheses of four novel benzimidazole-carbazole conjugates and demonstrate their high binding affinity to G4 DNA. S1 nuclease assay confirmed the ligand mediated G-quadruplex DNA protection. Additional evidence from Telomeric Repeat Amplification Protocol (TRAP-LIG) assay demonstrated efficient telomerase inhibition activity by the ligands. Two of the ligands showed IC 50 values in the sub-micromolar range in the TRAP-LIG assay, which are the best among the benzimidazole derivatives reported so far. The ligands also exhibited cancer cell selective nuclear internalization, nuclear condensation, fragmentation, and eventually antiproliferative activity in long-term cell viability assays. Annexin V-FITC/PI staining assays confirm that the cell death induced by the ligands follows an apoptotic pathway. An insight into the mode of ligand binding was obtained from the molecular dynamics simulations.

N-aryl-2-aminobenzimidazoles: Novel, efficacious, antimalarial lead compounds

From the phenotypic screening of the AstraZeneca corporate compound collection, N-aryl-2-aminobenzimidazoles have emerged as novel hits against the asexual blood stage of Plasmodium falciparum (Pf). Medicinal chemistry optimization of the potency against Pf and ADME properties resulted in the identification of 12 as a lead molecule. Compound 12 was efficacious in the P. berghei (Pb) model of malaria. This compound displayed an excellent pharmacokinetic profile with a long half-life (19 h) in rat blood. This profile led to an extended survival of animals for over 30 days following a dose of 50 mg/kg in the Pb malaria model. Compound 12 retains its potency against a panel of Pf isolates with known mechanisms of resistance. The fast killing observed in the in vitro parasite reduction ratio (PRR) assay coupled with the extended survival highlights the promise of this novel chemical class for the treatment of malaria.

Synthesis, DNA binding ability and anticancer activity of 2-heteroaryl substituted benzimidazoles linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates

As a continuation of our efforts to develop the benzimidazole-PBD conjugates as potential anticancer agents, a series of heteroaryl substituted benzimidazole linked PBD conjugates has been synthesized and evaluated for their anticancer potential in 60 human cancer cell lines. Most of the compounds exhibited promising anticancer activity and interestingly, compounds 4c and 4d displayed significant activity in most of the cell lines tested. Whereas, compound 4e showed selectivity in renal cancer cells with GI50 values of 10 and 70 nM against RXF 393 and UO-31 cell lines, respectively. Further, these compounds also showed significant DNA-binding affinity by thermal denaturation study using duplex form of calf thymus (CT) DNA.