13570-08-6

Usage

Uses

Used in Pharmaceutical Industry:
(1H-BENZOIMIDAZOL-2-YL)-ACETIC ACID is used as a key intermediate for the synthesis of benzisothiazole/benzimidazole derivatives with acidic groups. These derivatives are known for their numerous pharmacological properties, which can be leveraged to develop new drugs and therapies for various medical conditions.
Used in Drug Development:
(1H-BENZOIMIDAZOL-2-YL)-ACETIC ACID is utilized in the development of novel drugs with potential applications in treating a wide range of diseases and disorders. The acidic groups present in the benzisothiazole/benzimidazole derivatives synthesized using this intermediate contribute to their diverse pharmacological activities, making them valuable in the search for new therapeutic agents.
Used in Research and Development:
(1H-BENZOIMIDAZOL-2-YL)-ACETIC ACID is also employed in research and development efforts to explore the potential of benzisothiazole/benzimidazole derivatives with acidic groups. This includes studying their chemical properties, understanding their interactions with biological systems, and evaluating their efficacy and safety in preclinical and clinical trials.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 36, p. 1746, 1993 DOI: 10.1021/jm00064a008

InChI:InChI=1/C9H8N2O2/c12-9(13)5-8-10-6-3-1-2-4-7(6)11-8/h1-4H,5H2,(H,10,11)(H,12,13)

Upstream product

• 4414-88-4 1H-benzimidazol-2-acetonitrile 
• 141-82-2 malonic acid 
• 95-54-5 1,2-diamino-benzene 
• 107-91-5 cyanoacetic acid amide 
• 105-56-6 ethyl 2-cyanoacetate 
• 4981-92-4 1-benzylbenzimidazole 
• 51-17-2 benzoimidazole 
• 14741-71-0 ethyl (1H-benzimidazol-2-yl)acetate 
• 95-55-6 2-amino-phenol 

Downstream Products

• 14741-71-0 ethyl (1H-benzimidazol-2-yl)acetate 
• 1354647-68-9 ethyl 2-(1H-benzimidazol-2-yl)-3-(2-chlorophenyl)prop-2-enoate 
• 284497-05-8 ethyl 2-(1H-benzimidazol-2-yl)-3-(4-chlorophenyl)prop-2-enoate 
• 49672-05-1 methyl 2-(1H-benzo[d]imidazol-2-yl)acetate 
• 19731-02-3 2-(1H-benzo[d]imidazol-2-yl)acetohydrazide 

Relevant academic research and scientific papers

Design, synthesis, docking and QSAR study of substituted benzimidazole linked oxadiazole as cytotoxic agents, EGFR and erbB2 receptor inhibitors

The synthesis of benzimidazole linked oxadiazole derivatives designed as potential EGFR and erbB2 receptor inhibitors with anticancer and apoptotic activity were studied. Compounds 7a specifically inhibit EGFR and erbB2 receptor at 0.081 and 0.098 μM concentration. Some of the compounds showed strong, broad-spectrum antiproliferative activitiy when tested against five human cancer cell lines. Compounds 7a and 7n were more cytotoxic than 5-fluorouracil against MCF-7 cancer cell, with IC50values of 5.0 and 2.55 μM whereas, only 7a led to cell cycle arrest at G2/M phase accompanied by an increase in apoptosis. Compounds 7a and 7n showed normal architecture of myofibrils in cardiomyopathy study whereas only compound 7a showed nearly equal biochemical parameters (SGOT and SGPT) when compared to control. Molecular docking & 3D-QSAR studies were used to establish interactions of 7a and 7n within the active site of enzyme for ATP binding site of kinase domain.

Synthesis and pharmacological properties of benzisothiazole/benzimidazole derivatives with acidic groups

The synthesis and the pharmacological evaluation of benzisothiazole and benzimidazole tetrazolyl- and carboxyl- derivatives 1-6 are described. Structural modification was aimed at investigating the influence of two isosteric substituents (tetrazolyl- and

General base catalyzed ester hydrolysis as a model of the ''charge relay'' system

The validity of the 'charge relay' system in serine esterases was examined by use of the general base catalyzed hydrolysis of ethyl chloroacetate (I) as a model system. The general base catalytic rate for 2 benzimidazoleacetic acid (II) exhibited an eightfold positive deviation from the Bronsted plot including benzimidazole, imidazole, N methylimidazole (V), and acetate ion, though in nucleophilic catalysis of the hydrolysis of p nitrophenyl acetate, the point for II conformed to the Bronsted relationship together with imidazole and benzimidazole derivatives. The positive deviation of II from the Bronsted plot for the general base catalysis was attributed to the cooperativety of the carboxyl group of II, the imidazolyl group of II, and the hydroxyl group of water. The present result provides support for the 'charge relay' system. Furthermore, the (essentially) total loss of the enzymatic activity due to N 3 methylation of histidine 57 in α chymotrypsin is discussed in comparison to the general base catalysis of V in the hydrolysis of I, which is also favorable for the 'charge relay' system.

Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles)

A series of bis(amidinobenzimidazoles) and bis(amidinoindoles) with varied linking chains connecting the aromatic groups and various modifications to the basic amidino groups have been prepared. The calf thymus (CT) DNA and nucleic acid homopolymer [poly(dA)·poly(dT), poly(dA-dT)·poly-(dA-dT), and poly(dG-dC)·poly(dG-dC)] binding properties of these compounds have been studied by thermal denaturation (ΔT(m)) and viscosity. The compounds show a greater affinity for poly(dA)·poly(dT) and poly(dA-dT)·poly(dA-dT) than for poly(dG-dC)·poly(dG-dC). Viscometric titrations indicate that the compounds do not bind by intercalation. Molecular modeling studies and the biophysical data suggest that the molecules bind to the minor groove of CT DNA and homopolymers. Analysis of the shape of the molecules is consistent with this mode of nucleic acid binding. Compounds with an even number of methylenes connecting the benzimidazole rings have a higher affinity for DNA than those with an odd number of methylenes. Molecular modeling calculations that determine the radius of curvature of four defined groups in the molecule show that the shape of the molecule, as a function of chain length, affects the strength of nucleic acid binding. Electronic effects from cationic substituents as well as hydrogen bonding from the imidazole nitrogens also contribute to the nucleic acid affinity. The bis(amidinoindoles) show no structurally associated differential in nucleic acid base pair specificity or affinity.

An efficient synthesis of novel di-heterocyclic benzazole derivatives and evaluation of their antiproliferative activities

A series of unsymmetrical nine di-heterocyclic compounds of benzazole derivatives were synthesized at one step via cyclization reaction. The compounds evaluated for in?vitro cytotoxic activity against A549, A498, HeLa, and HepG2 cancer cell lines. The biological evaluation results show that 23, 26 and 29 exhibit better activity against HepG2 and HeLa cancer cell lines. Compound 23 also showed good activity against A549, and A498 cancer cell lines. The analogs were further performed molecular docking studies against human cytochrome P450 2C8 monooxygenase enzyme, calculated some theoretical quantum parameters, ADMET descriptor and molecular electrostatic potential analysis. The strategy applied in this research work may act as a perspective for the rational design of potential anticancer drugs. Communicated by Ramaswamy H. Sarma.

Composition based on benzimidazole carboxylic acid compound and application thereof

The invention belongs to the field of medicine and pharmacology, and particularly relates to a pharmaceutical composition taking benzimidazole carboxylic acid and pharmaceutically acceptable salt thereof as active ingredients. The pharmaceutical composition taking the benzimidazole carboxylic acid and pharmaceutically acceptable salt thereof as main active ingredients is used for preventing and/ortreating respiratory tract reaction and nasal congestion caused by allergic reaction, nasal congestion caused by other reasons and other symptoms, and can realize immediate and/or lasting alleviationof congestion. The invention also provides a method of treating and/or alleviating and/or preventing nasal congestion in a patient, the method comprising administering to a patient in need thereof aneffective amount of the pharmaceutical composition of the benzimidazole carboxylic acid or a pharmaceutically acceptable salt thereof.

NOVEL FERROPORTIN INHIBITORS

The invention relates to novel ferroportin inhibitors of the general formula (I) pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for the prophylaxis and/or treatment of diseases caused by a lack of hepcidin or iron metabolism disorders, such as particularly iron overload states such as in particular thalassemia and hemochromatosis.

Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease

In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from Aβ-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD.

BENZIMIDAZOLE DERIVATIVES AS MITOCHONDRIAL FUNCTION MODULATORS

Provided are a benzimidazole derivative modulating mitochondrial functions and having pharmaceutical activity as a neuro-protective agent, and a pharmaceutical composition including the compound as an active ingredient.

Antipsychotic benzimidazole derivatives

A class of benzimidazole derivatives, substituted at the 2-position by a substituted piperazinylmethyl or piperazinylethyl moiety, are antagonists of dopamine receptor subtypes within the brain, having a selective affinity for the dopamine D 4 receptor su