3042-00-0

Basic information

• Product Name: (2-BENZIMIDAZOLYLTHIO)ACETIC ACID
• Synonyms: ASISCHEM N48906;AURORA 5436;LABOTEST-BB LT00255555;AKOS AU36-M68;AKOS BBS-00005718;2-(CARBOXYMETHYLTHIO)BENZIMIDAZOLE;(2-BENZIMIDAZOLYLTHIO)ACETIC ACID;(2-BENZIMIDAZOLYTHIO)ACETIC ACID
• CAS NO: 3042-00-0
• Molecular Formula: C₉H₈N₂O₂S
• Molecular Weight: 208.24
• Product Categories: Imidazol&Benzimidazole
• Mol File: 3042-00-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 214-215°C (dec.)
• Boiling Point: 475.3 °C at 760 mmHg
• Flash Point: 241.3 °C
• Appearance: off white solid
• Density: 1.5 g/cm³
• Vapor Pressure: 7.69E-10mmHg at 25°C
• PKA: 2.72±0.10(Predicted)
• BRN: 11825
• CAS DataBase Reference: (2-BENZIMIDAZOLYLTHIO)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2-BENZIMIDAZOLYLTHIO)ACETIC ACID(3042-00-0)
• EPA Substance Registry System: (2-BENZIMIDAZOLYLTHIO)ACETIC ACID(3042-00-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 3042-00-0(Hazardous Substances Data)

Usage

General Description

(2-Benzimidazolylthio)acetic acid is a chemical compound that is commonly used in pharmaceutical research and drug development. It is classified as a thiazolidinedione derivative, which is a class of drugs known for their potential use in the treatment of diabetes and other metabolic disorders. The compound is a potent inhibitor of peroxisome proliferator-activated receptor gamma (PPARγ), a nuclear receptor that plays a key role in the regulation of glucose and lipid metabolism. This makes (2-Benzimidazolylthio)acetic acid a promising candidate for the development of new medications for managing diabetes and related metabolic conditions. Additionally, it may have potential applications in research related to cancer, inflammation, and neurodegenerative diseases.

InChI:InChI=1/C9H8N2O2S/c12-8(13)5-14-9-10-6-3-1-2-4-7(6)11-9/h1-4H,5H2,(H,10,11)(H,12,13)/p-1

Upstream product

• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 79-11-8 chloroacetic acid 
• 79-08-3 bromoacetic acid 
• 134469-07-1 Benzimidazol-2-thiol 
• 64-18-6 formic acid 
• 174621-79-5 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile 
• 95-54-5 1,2-diamino-benzene 
• 3926-62-3 sodium monochloroacetic acid 
• 6268-88-8 1-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione 
• 132380-68-8 C₉H₇N₂O₂S^(1-)*K⁽¹⁺⁾ 
• 175733-64-9 2-(1H-Benzoimidazol-2-ylsulfanyl)-malononitrile 
• 5429-62-9 ethyl 2-(1H-benzo[d]imidazol-2-ylthio)acetate 

Downstream Products

• 3042-01-1 thiazolo[3,2-a]benzimidazol-3(2H)-one 
• 79420-24-9 2-(1H-Benzoimidazol-2-ylsulfanyl)-N-benzothiazol-2-yl-acetamide 
• 511283-88-8 2-(1H-Benzoimidazol-2-ylsulfanyl)-N-(4-hydroxy-phenyl)-acetamide 
• 30065-35-1 2-(1H-benzo[d]imidazol-2-ylthio)-N-(4-methylphenyl)acetamide 
• 41215-89-8 2-(1H-benzoimidazol-2-ylsulfanyl)-N-(4-chloro-phenyl)-acetamide 
• 86109-62-8 2-(1H-benzo[d]imidazol-2-ylthio)-N-(4-acetylphenyl)acetamide 
• 30065-36-2 2-(1H-benzo[d]imidazol-2-ylthio)-N-(4-methoxyphenyl)acetamide 
• 86109-64-0 4-(2-(1H-benzo[d]imidazol-2-ylthio) acetamido)benzoic acid 
• 41215-93-4 2-(1H-benzoimidazol-2-ylsulfanyl)-N-(4-nitro-phenyl)-acetamide 
• 356776-28-8 2-(1H-benzo[d]imidazole-2-ylthio)-N-(2-nitrophenyl)acetamide 
• 30065-33-9 2-(1H-benzo[d]imidazol-2-ylthio)-N-phenylacetamide 
• 361184-65-8 2-(1H-benzo[d]imidazol-2-ylthio)-N-(2-chlorophenyl)acetamide 
• 30065-32-8 2-((1H-benzo[d]imidazol-2-yl)thio)-N-benzylacetamide 
• 86109-61-7 2-(1H-benzo[d]imidazol-2-ylthio)-N-(4-bromophenyl)acetamide 

Relevant articles and documents

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Head-to-head bisbenzazole derivatives as antiproliferative agents: design, synthesis, in vitro activity, and SAR analysis

Abstract: In the present work, a series of bisbenzazole derivatives were designed and synthesized as antiproliferative agents. The antiproliferative activity of these compounds was investigated using MTT assay. Bisbenzazole derivatives showed significant antiproliferative activity against all the four tested cancer cell lines. Among the various bisbenzazole derivatives, bisbenzoxazole derivatives exhibited the most promising anticancer activity followed by bisbenzimidazole and bisbenzothiazole derivatives. All the derivatives were found to be less toxic as compared to methotrexate (positive control) in normal human cells, indicating selective and efficient antiproliferative activity of these bisbenzazole derivatives. The structure–activity relationships of heteroaromatic systems and linkers present in bisbenzazole derivatives were analyzed in detail. In silico ADMET prediction revealed that bisbenzazole is a drug-like small molecule with a favorable safety profile. Compound 31 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from methotrexate. Graphic abstract: Twenty-one bisbenzoxazole derivatives have been designed synthesized and evaluated to be an antiproliferative activity against four human tumor cell lines.[Figure not available: see fulltext.]

Amino acid conjugates of 2-mercaptobenzimidazole provide better anti-inflammatory pharmacology and improved toxicity profile

Benzimidazole is an important pharmacophore for clinically active drugs against inflammation and treatment of pain, however, it is associated with gastrointestinal side effects. Here we synthesized benzimidazole based agents with significant analgesic/anti-inflammatory potential but with less gastrointestinal adverse effects. In this study, we synthesized novel, orally bioavailable 2-mercaptobenzimidazole amino acid conjugates (4a–4o) and screened them for analgesic, anti-inflammatory and gastro-protective effects. The synthesized 2-mercaptbenzimidazole derivatives were characterized for their structure using FTIR, 1H NMR and 13C NMR spectroscopic techniques. The 2-mercaptobenzimidazole amino acid conjugates have found to possess potent analgesic, anti-inflammatory and gastroprotective activities, particularly with compound 4j and 4k. Most of the compounds exhibited remarkable anti-ulcer and antisecretory effects. Molecular docking studies were carried out to study the binding affinities and interactions of the synthesized compounds with target proteins COX-2 (PDB ID: 3LN1) and H+/K+-ATPase (PDB ID: 5Y0B). Our results support the clinical promise of these newly synthesized 2-mercaptobezimidazol conjugates as a component of therapeutic strategies for inflammation and analgesia, for which the gastric side effects are always a major limitation.