23249-97-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzimidazolepropionic acid is used as a reagent for the generation of monoclonal antibodies against very small drug haptens, such as 5-benzimidazolecarboxylic acid, through both in vivo immunization methods and in vitro immunization procedures.
Used in Chemical Synthesis:
2-Benzimidazolepropionic acid is used as a key component in the synthesis of cytidine derivatives, which are important for various applications in the pharmaceutical and chemical industries.
Used in Antimalarial Applications:
2-Benzimidazolepropionic acid is used as an antimalarial agent due to its reported active antimalarial activity, potentially offering a new avenue for the development of treatments against malaria.

InChI:InChI=1/C10H10N2O2/c13-10(14)6-5-9-11-7-3-1-2-4-8(7)12-9/h1-4H,5-6H2,(H,11,12)(H,13,14)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 64-17-5 ethanol 
• 95-54-5 1,2-diamino-benzene 
• 71-43-2 benzene 
• 110-15-6 succinic acid 
• 19950-82-4 2,3-dihydro-1H-pyrrolo<1,2-a>benzimidazole-1-one 
• 7647-01-0 hydrogenchloride 
• 5838-57-3 2-(but-3-en-1-yl)-1H-benzo[d]imidazole 
• 67-56-1 methanol 
• 1156151-44-8 C₆H₁₁NO₄ 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 83549-10-4 o-aminosuccinanilic acid 

Downstream Products

• 53004-64-1 3-(2-Benzimidazolyl)-acrylsaeure 
• 19950-82-4 2,3-dihydro-1H-pyrrolo<1,2-a>benzimidazole-1-one 
• 103706-44-1 Acetic acid 4-[1-oxo-1,2-dihydro-benzo[d]pyrrolo[1,2-a]imidazol-(3E)-ylidenemethyl]-phenyl ester 
• 6315-23-7 3-(1H-benzimidazol-2-yl)-propionic acid ethyl ester 
• 103706-45-2 Acetic acid 2-[1-oxo-1,2-dihydro-benzo[d]pyrrolo[1,2-a]imidazol-(3E)-ylidenemethyl]-phenyl ester 
• 103706-50-9 3-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-2,3-dihydro-benzo[d]pyrrolo[1,2-a]imidazol-1-one 
• 176389-00-7 (2R,3R,4S)-2-{4-[(3-1H-Benzoimidazol-2-yl-propionylamino)-methyl]-benzylamino}-4-tert-butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid ethyl ester 
• 24786-76-3 β-(1-Methylbenzimidazol-2-yl)-propionsaeuremethylester 
• 1055033-76-5 (2R,3R,4S)-2-{4-[(3-1H-Benzoimidazol-2-yl-propionylamino)-methyl]-benzylamino}-4-tert-butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid 
• 26209-49-4 3-(1H-benzoimidazol-2-yl)-propionamide 
• 143949-72-8 3-(1H-benzoimidazol-2-yl)-propionic acid hydrazide 
• 24786-75-2 3-(1-methyl-1H-benzoimidazol-2-yl)-propionic acid 
• 916141-29-2 (S)-1-(3-(1H-benzo[d]imidazol-2-yl)propanoyl)-N-([1,1'-biphenyl]-2-yl)pyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

A unique 2D framework containing linear trimeric cobalt(ii) of mixed T d-Oh-Td geometries linked by two different single-carboxylate-aromatic amine ligands: Structure and magnetic properties

A new 2D coordination polymer Co3(OH)2(pa) 2(ina)2 (1, pa = 3-(1H-benzimidazol-2-yl) propanoic carboxylate, ina = isonicotinate) contained uncommon, linear Co(ii) trimers of mixed Td-Oh-Td geometries, exhibits spin canting below 20 K. Such magnetic behavior mainly arises from the Dzyaloshinski-Moriya interaction from the anisotropic, mixed geometries trimeric Co(ii) ions to the crimpled 2D network based on the nature of the binding modes of Co(ii)-carboxylate trimer and the effect of the intertrimers arrangement of 1. The mixed single-carboxylate-aromatic amine ligands bridged metal systems display a new structurally authenticated example of a thick 2D layer, and also indicate homometallic Co(ii) clusters with Td-Oh-T d mixed-geometries can result in relatively obvious noncompensation moments, according to different efficient spins of Co(ii) at very low temperature, in spite of antiferromagnetic intracluster interactions. The Royal Society of Chemistry.

Design, synthesis and biological evaluation of benzimidazole derivatives as novel human Pin1 inhibitors

In this work, a series of novel benzimidazole derivatives were designed and synthesized as Pin1 inhibitors. Protease-coupled assay was used to investigate the Pin1 inhibitory potency of all synthesized compounds. Thirteen of them showed preferable Pin1 inhibitory effects with IC50 values lower than 5 μM, and 12a, 15b, 15d and 16c exhibited the most promising Pin1 inhibitory activity at low micromolar level (0.33–1.00 μM) than the positive control compound Juglone. Flow cytometry results showed that treating PC-3 cells with 16c caused slight cycle arrest in a concentration-dependent manner. The structure-activity relationships of R1, R2, R3 and linker of the benzimidazole derivatives were analyzed in detail, which would help further exploration of new Pin1 inhibitors.

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.

Hit-to-Lead Optimization and Discovery of 5-((5-([1,1′-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase

AMP-activated protein kinase (AMPK) plays an essential role as a cellular energy sensor and master regulator of metabolism in eukaryotes. Dysregulated lipid and carbohydrate metabolism resulting from insulin resistance leads to hyperglycemia, the hallmark of type 2 diabetes mellitus (T2DM). While pharmacological activation of AMPK is anticipated to improve these parameters, the discovery of selective, direct activators has proven challenging. We now describe a hit-to-lead effort resulting in the discovery of a potent and selective class of benzimidazole-based direct AMPK activators, exemplified by 5-((5-([1,1′-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid, 42 (MK-3903). Compound 42 exhibited robust target engagement in mouse liver following oral dosing, leading to improved lipid metabolism and insulin sensitization in mice.

18 beta-glycyrrhetinic acid derivative and application thereof

The invention relates to the technical field of medicines, in particular to an 18 beta-glycyrrhetinic acid derivative with Pin1 inhibitory activity and pharmacologically-acceptable salt thereof, a preparation method of the derivative, a pharmaceutical composition taking the derivative as an active ingredient and application of the derivative to the preparation of a Pin1 inhibitor and the preparation of a drug for treating and/or preventing various cancers. The derivative shown in a general formula I or the pharmacologically-acceptable salt thereof has the following structure, wherein R, X, Y and n are stated in the claims and the descriptions.

Conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid as Pin1 inhibitors displaying anti-prostate cancer ability

Twenty-six conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid were designed and synthesized as Pin1 inhibitors. Most of these semi-synthetic compounds showed improved Pin1 inhibitory activity and anti-proliferative effects against prostate cancer cells as compared to 3-(1H-benzo[d]imidazol-2-yl)propanoic acid and GA. Compounds 10a and 12i were the most potent to inhibit growth of prostate cancer PC-3 with GI50 values of 7.80 μM and 3.52 μM, respectively. The enzyme inhibition ratio of nine compounds at 10 μM was over 90%. Structure-activity relationships indicated that both appropriate structure at ring C of GA and suitable length of linker between GA skeleton and benzimidazole moiety had significant impact on improving activity. Western blot assay revealed that 10a decreased the level of cell cycle regulating protein cyclin D1. Thus, these compounds might represent a novel anti-proliferative agent working through Pin1 inhibition.

Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles

One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy.

Functionalized orthoesters as powerful building blocks for the efficient preparation of heteroaromatic bicycles

By combining substituted anilines with functionalized orthoesters, an efficient and connective methodology for the preparation of benzoxazole, benzothiazole, and benzimidazole derivatives has been established. The versatility of this approach enables the development of new libraries of heterocycles containing multifunctional sites.

Boric acid-catalyzed direct condensation of carboxylic acids with benzene-1,2-diamine into benzimidazoles

The applicability of boric acid catalysis for the direct condensation of carboxylic acids with benzene-1,2-diamine to give 2-substituted benzimidazoles was investigated. It was found that catalytic amounts (5-10 mol-%) of boric acid efficiently promote the cyclocondensation of aliphatic carboxylic acids in refluxing toluene. In addition, the relatively neutral conditions allow the use of acid-sensitive substrates and give rise to specific transformations and selectivities that are not observed with some classical methods. Benzoic acids were found to be less reactive than aliphatic acids and thus require refluxing xylene for better efficiency. Phenylboronic acid was found to be inactive as a catalyst due to its rapid consumption by condensation with benzene-1,2-diamine to give a 2-phenylbenzodiazaborole. Copyright