69570-97-4

Usage

Structure

A heterocyclic compound containing a benzene ring fused to an imidazole ring

Type

Methyl ester derivative of 1H-Benzimidazole-5-carboxylic acid, 2-phenyl-

Usage

Commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals

Biological activities

Has potential biological activities and is being studied for its potential therapeutic applications

Interest

Of interest to researchers and chemists due to its versatile reactivity and potential for drug development.

Upstream product

• 36692-49-6 Methyl 3,4-diaminobenzoate 
• 65-85-0 benzoic acid 
• 873-67-6 benzonitrile oxide 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 3987-92-6 methyl 4-amino-3-nitrobenzoate 
• 86255-36-9 N-(2-amino-5-methoxycarbonylphenyl)benzamide oxime 
• 19718-49-1 4-amino-3-iodobenzoic acid methyl ester 

Downstream Products

• 66630-70-4 2-phenyl-1H-1,3-benzimidazole-5-carboxylic acid 
• 66630-70-4 2-phenyl-1H-benzo[d]imidazole-6-carboxylic acid 
• 3925-93-7 5-hydroxymethyl-2-phenyl-benzimidazole 
• 174648-21-6 2-phenyl-1H-benzo[d]imidazole-6-carbaldehyde 
• 361457-34-3 5-hydroxymethyl-2-phenylbenzimidazole 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles as inhibitors of ebola virus infection

Novel 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles were designed and synthesized as Ebola virus inhibitors. The proposed structures of the new prepared benzimidazole-piperidine hybrids were confirmed based on their spectral data and CHN analyses. The target compounds were screened in vitro for their anti-Ebola activity. Among tested molecules, compounds 26a (EC50=0.93 μM, SI = 10) and 25a (EC50=0.64 μM, SI = 20) were as potent as and more selective than Toremifene reference drug (EC50 = 0.38 μM, SI = 7) against cell line. Data suggests that the mechanism by which 25a and 26a block EBOV infection is through the inhibition of viral entry at the level of NPC1. Furthermore, a docking study revealed that several of the NPC1 amino acids that participate in binding to GP are involved in the binding of the most active compounds 25a and 26a. Finally, in silico ADME prediction indicates that 26a is an idealy drug-like candidate. Our results could enable the development of small molecule drug capable of inhibiting Ebola virus, especially at the viral entry step.

Design, synthesis and biological evaluation: 5-amino-1h-pyrazole-1-carbonyl derivatives as fgfr inhibitors

Background: Fibroblast growth factors (FGFs) and their high affinity receptors (FGFRs) play a major role in cell proliferation, differentiation, migration, and apoptosis. Aberrant FGFR signaling pathway might accelerate development in a broad panel of mal

Method for preparing benzimidazole and quinazoline compounds by adopting supported nickel catalyst (by machine translation)

The invention discloses a method for synthesizing benzimidazole and quinazoline compounds by oxidative coupling and dehydrogenation of a nitrogen-doped hierarchical porous biomass-based carbon material supported catalyst and a preparation method. The method comprises the following steps: adding o-phenylenediamine compound, alcohol, supported catalyst, toluene and potassium tert-butoxide as a solvent, carrying out reaction under 50~150 °C conditions, carrying out reaction 4~24 hours, cooling to room temperature, filtering the reaction liquid, and obtaining a benzimidazole compound or quinazoline compound. The method adopts "one-pot method" preparation, the intermediate can be separated and purified, energy consumption can be reduced, and the efficiency. (by machine translation)

Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon

A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

Structure-Guided Synthesis and Evaluation of Small-Molecule Inhibitors Targeting Protein–Protein Interactions of BRCA1 tBRCT Domain

The tandem BRCT domains (tBRCT) of BRCA1 engage phosphoserine-containing motifs in target proteins to propagate intracellular signals initiated by DNA damage, thereby controlling cell cycle arrest and DNA repair. Recently, we identified Bractoppin, the fi

Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies.

PIPERAZINE DERIVATIVES AS MAGL INHIBITORS

The invention provides new heterocyclic compounds having general Formula (I), or a pharmaceutically acceptable salt thereof, wherein R1, R2, X, Y1 and Y2 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

BENZIMIDAZOL DERIVATIVES FOR TREATING FILOVIRUS INFECTION

The present invention relates to compounds comprising a benzimidazole scaffold, and the use of such compounds for the treatment of viral diseases. The invention also relates to pharmaceutical compositions comprising said compounds as an active ingredient. In particular the compounds of the invention comprising a benzimidazole scaffold are used for the treatment of filoviruses or retroviruses, and preferably for the treatment of Ebola virus or HIV virus.

Targeting Phosphopeptide Recognition by the Human BRCA1 Tandem BRCT Domain to Interrupt BRCA1-Dependent Signaling

Intracellular signals triggered by DNA breakage flow through proteins containing BRCT (BRCA1 C-terminal) domains. This family, comprising 23 conserved phosphopeptide-binding modules in man, is inaccessible to small-molecule chemical inhibitors. Here, we develop Bractoppin, a drug-like inhibitor of phosphopeptide recognition by the human BRCA1 tandem (t)BRCT domain, which selectively inhibits substrate binding with nanomolar potency in vitro. Structure-activity exploration suggests that Bractoppin engages BRCA1 tBRCT residues recognizing pSer in the consensus motif, pSer-Pro-Thr-Phe, plus an abutting hydrophobic pocket that is distinct in structurally related BRCT domains, conferring selectivity. In cells, Bractoppin inhibits substrate recognition detected by F?rster resonance energy transfer, and diminishes BRCA1 recruitment to DNA breaks, in turn suppressing damage-induced G2 arrest and assembly of the recombinase, RAD51. But damage-induced MDC1 recruitment, single-stranded DNA (ssDNA) generation, and TOPBP1 recruitment remain unaffected. Thus, an inhibitor of phosphopeptide recognition selectively interrupts BRCA1 tBRCT-dependent signals evoked by DNA damage. Periasamy et al. report the development of Bractoppin, a drug-like inhibitor of phosphopeptide recognition by the BRCA1 tBRCT domain, opening avenues to block intracellular signaling via a family of related targets.

Synthesis of 2-arylbenzimidazole analogues

Substituted 2-arylbenzimidazoles (4) were easily synthesized in good yields starting from the condensation reaction of 1,2-diaminobenzenes (1) with β-ketosulfones (5) in the presence of boiling HOAc.