83783-69-1

Basic information

• Product Name: 2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI&
• Synonyms: 2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI&;2-amino-1-[(4-fluorophenyl)methyl]-1H-benzimidazole;4-FLUORBENZYL-1H-BENZIMIDAZOOL-2-YLAMINE;1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-amine;Einecs 280-803-2;1H-Benzimidazol-2-amine, 1-[(4-fluorophenyl)methyl]-;1-(4-fluorobenzyl)-1H-benzimidazol-2-amine(SALTDATA: FREE);1-(4-fluorobenzyl)-1H-benzimidazol-2-amine
• CAS NO: 83783-69-1
• Molecular Formula: C₁₄H₁₂FN₃
• Molecular Weight: 241.2635832
• EINECS: 280-803-2
• Mol File: 83783-69-1.mol

Chemical Properties

• Boiling Point: 456.7 °C at 760 mmHg
• Flash Point: 230 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 1.58E-08mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: 2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI&(83783-69-1)
• EPA Substance Registry System: 2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI&(83783-69-1)

Safety Data

• Hazardous Substances Data: 83783-69-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI& is used as a chemical intermediate for the synthesis of various pharmaceuticals due to its potential biological activities. It plays a crucial role in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Chemical Synthesis:
In the chemical industry, 2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI& is used as a building block in the synthesis of complex organic molecules. Its unique structure allows for the creation of a variety of compounds with different applications in various fields.
Used in Medicinal Chemistry:
2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI& is employed as a key component in the design and synthesis of novel therapeutic agents. Its structural features enable the development of molecules with specific biological targets, potentially leading to the discovery of new drugs with improved efficacy and safety profiles.
Used in Biochemical Studies:
2-AMINO-1-((4-FLUOROPHENYL)METHYL)BENZI& is also utilized in biochemical research to investigate its interactions with various biological systems. Understanding these interactions can provide insights into the molecular mechanisms of diseases and contribute to the development of targeted therapies.

InChI:InChI=1/C14H12FN3/c15-11-7-5-10(6-8-11)9-18-13-4-2-1-3-12(13)17-14(18)16/h1-8H,9H2,(H2,16,17)

Upstream product

• 934-32-7 1H-benzimidazol-2-amine 
• 420-04-2 CYANAMID 
• 7191-70-0 N-(4''-fluorobenzyl)-1,2-phenylenediamine 
• 459-46-1 4-Fluorobenzyl bromide 
• 506-68-3 bromocyane 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 95-54-5 1,2-diamino-benzene 
• 1093981-22-6 2-azido-1-(4-fluorobenzyl)-1H-benzo[d]imidazole 
• 3978-80-1 Boc-Tyr-OH 
• 124443-67-0 1-[(4-fluorophenyl)methyl]-1H-benzimidazole 
• 67-56-1 methanol 
• 51-17-2 benzoimidazole 

Downstream Products

• 144836-28-2 [1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-[1-(4-fluoro-benzyl)-1H-benzoimidazol-2-yl]-amine 
• 144836-24-8 [1-(4-Fluoro-benzyl)-1H-benzoimidazol-2-yl]-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-amine 
• 144836-20-4 4-{[(E)-1-(4-Fluoro-benzyl)-1H-benzoimidazol-2-ylimino]-methyl}-2-methoxy-phenol 
• 144836-42-0 4-{[1-(4-Fluoro-benzyl)-1H-benzoimidazol-2-ylamino]-methyl}-2-methoxy-6-morpholin-4-ylmethyl-phenol 
• 144836-36-2 [1-(4-Fluoro-benzyl)-1H-benzoimidazol-2-yl]-(3,4,5-trimethoxy-benzyl)-amine 
• 144836-40-8 Benzo[1,3]dioxol-5-ylmethyl-[1-(4-fluoro-benzyl)-1H-benzoimidazol-2-yl]-amine 
• 144836-32-8 4-{[1-(4-Fluoro-benzyl)-1H-benzoimidazol-2-ylamino]-methyl}-2-methoxy-phenol 

Relevant articles and documents

Structure-Guided Development of Small-Molecule PRC2 Inhibitors Targeting EZH2-EED Interaction

Disruption of EZH2-embryonic ectoderm development (EED) protein-protein interaction (PPI) is a new promising cancer therapeutic strategy. We have previously reported the discovery of astemizole, a small-molecule inhibitor targeting the EZH2-EED PPI. Herein, we report the cocrystal structure of EED in complex with astemizole at 2.15 ?. The structure elucidates the detailed binding mode of astemizole to EED and provides a structure-guided design for the discovery of a novel EZH2-EED interaction inhibitor, DC-PRC2in-01, with an affinityKdof 4.56 μM. DC-PRC2in-01 destabilizes the PRC2 complex, thereby leading to the degradation of PRC2 core proteins and the decrease of global H3K27me3 levels in cancer cells. The proliferation of PRC2-driven lymphomas cells is effectively inhibited, and the cell cycle is arrested in the G0/G1 phase. Together, these data demonstrate that DC-PRC2in-01 could be an effective chemical probe for investigating the PRC2-related physiology and pathology and providing a promising chemical scaffold for further development.

Substituted benzimidazoles as modulators of Ras signaling

Benzimidazole compounds that increase the rate of SOS-mediated nucleotide exchange on Ras by binding to a functionally relevant, chemically tractable pocket on the SOS protein, as part of the Ras:SOS:Ras complex.

A novel 2-aminobenzimidazole-based compound Jzu 17 exhibits anti-angiogenesis effects by targeting VEGFR-2 signalling

Background and Purpose: Recent development in drug discovery have shown benzimidazole to be an important pharmacophore,. Benzimidazole derivatives exhibit broad-spectrum pharmacological properties including anti-microbial, anti-diabetic and anti-tumour activity. However, whether benzimidazole derivatives are effective in suppressing angiogenesis and its underlying mechanisms remain incompletely understood. In this study, we aim to characterize the anti-angiogenic mechanisms of a novel 2-aminobenzimidazole-based compound, Jzu 17, in an effort to develop novel angiogenesis inhibitor. Experimental Approach: Effects of Jzu 17 on endothelial cell proliferation, migration, invasion, and activation of signalling molecules induced by VEGF-A, were analysed by immunoblotting, MTT, BrdU, migration, and invasion assays. We performed tube formation assay, aorta ring sprouting assay, matrigel plug assay, and a mouse model of metastasis to evaluate ex vivo and in vivo anti-angiogenic effects of Jzu 17. Key Results: Jzu 17 inhibited VEGF-A-induced cell proliferation, migration, invasion, and endothelial tube formation of HUVECs. Jzu 17 suppressed VEGF-A-induced microvessel sprouting ex vivo and attenuated VEGF-A- or tumour cell-induced neovascularization in vivo. Jzu 17 also reduced B16F10 melanoma lung metastasis. In addition, Jzu 17 inhibited the phosphorylation of VEGFR-2 and its downstream signalling molecules in VEGF-A-stimulated HUVECs. Results from computer modelling further showed that Jzu 17 binds to VEGFR-2 with high affinity. Conclusions and Implications: Jzu 17 may inhibit endothelial remodelling and suppress angiogenesis through targeting VEGF-A-VEGFR-2 signalling. These results also suggest Jzu 17 as a potential lead compound and warrant the clinical development of similar agents in the treatment of cancer and angiogenesis-related diseases.

Water compatible photoarylation of amino acids and peptides

A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.

Photochemical arylation of Bronsted acids with 2-azidobenzimidazole

Irradiation of N-benzylated 2-azidobenzimidazoles at 300 nm in the presence of an excess amount of carboxylic acids results in a novel regioselective synthesis of 2-amino-6-oxybenzimidazoles in isolated yields of 60-70 %. It is also possible to regioselectively introduce 6-bromo, 6-chloro, and 6-triflyloxy groups. Irradiation in dichloromethane in the absence of external nucleophiles revealed that after loss of nitrogen, the benzimidazolylnitrene probably undergoes coarctate ring opening to an N-cyano diaza-o-xylylene intermediate. Photolysis of 2-azidobenzimidazoles in the presence of carboxylic or sulfonic acidsleads to regioselective oxygenation of the 6-position in good yield. Copyright

Synthesis and?QSAR studies of?novel 1-substituted-2-aminobenzimidazoles derivatives

A series of novel 1-substituted-2-aminobenzimidazole derivatives were synthesized. The structures of the synthesized compounds were confirmed by 1H-NMR spectra and by elemental analysis. Acute toxicities of these compounds were detected on mice via toxicity (logLD50). QSAR analysis of these chemicals was studied on the relationship between acute toxicity and the octanol/water partition coefficient (LogP). The products were identified by the results of elemental analysis and 1H-NMR spectra. The toxicity (logLD50) of 2-aminobenzimidazole 1-substituents were correlated well with the partition coefficient LogP, r = 0.9243. The bioactivity (toxicity) of 2-aminobenzimidazoles can be predicted by the molecular structural parameter such as LogP.

((Pharmacologically active bicyclic heterocyclic)methyl and -heteroatom) substituted hexahydro-1H-azepines and pyrrolidines

[(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-1H-azepines and pyrrolidines and their pharmaceutically acceptable acid addition salts having anti-histaminic properties, compositions containing the same, and methods of treating allergic diseases in warm-blooded animals.