58089-25-1

Basic information

• Product Name: 2-MERCAPTO-5-BENZIMIDAZOLECARBOXYLIC ACID
• Synonyms: 2H-BENZIMIDAZOLINETHIONE-5-CARBOXYLIC ACID;2-MERCAPTO-5-BENZIMIDAZOLECARBOXYLIC ACID;2-MERCAPTO-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID;2-MERCAPTO-1H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID;2-THIO-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID;2-Mercapto-5-caroxyl benzimidazole;5-Carboxylic Acid-2-Mercapto Benzimidazole;2-Mercapto-5-carboxylbenzimidazole
• CAS NO: 58089-25-1
• Molecular Formula: C₈H₆N₂O₂S
• Molecular Weight: 194.21
• Product Categories: BENZIMIDAZOLE;pharmacetical;Carboxylic Acids;Imidazoles & Benzimidazoles;Imidazol&Benzimidazole;Carboxylic Acids;Imidazoles & Benzimidazoles
• Mol File: 58089-25-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: >290℃
• Boiling Point: 413 °C at 760 mmHg
• Flash Point: 203.6 °C
• Appearance: /
• Density: 1.63
• Vapor Pressure: 1.46E-07mmHg at 25°C
• Refractive Index: 1.783
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.33±0.20(Predicted)
• CAS DataBase Reference: 2-MERCAPTO-5-BENZIMIDAZOLECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MERCAPTO-5-BENZIMIDAZOLECARBOXYLIC ACID(58089-25-1)
• EPA Substance Registry System: 2-MERCAPTO-5-BENZIMIDAZOLECARBOXYLIC ACID(58089-25-1)

Safety Data

• Hazardous Substances Data: 58089-25-1(Hazardous Substances Data)

Usage

General Description

2-Mercapto-5-Benzimidazolecarboxylic Acid (MBICA) is a chemical compound known for its wide application in the field of chemistry. It consists of a benzimidazole ring, which is a key structure component in several types of medications, along with carboxylic acid and a sulfur-containing group (mercapto), which confers unique characteristics to the chemical. 2-MERCAPTO-5-BENZIMIDAZOLECARBOXYLIC ACID is typically used as an intermediate in the synthesis of a variety of pharmaceutical and fine chemical products. Despite its broad application in chemical synthesis, it needs careful handling due to its hazardous potential. Specific data on its toxicity and environmental impact, however, may vary and should be understood clearly before the use of this chemical.

InChI:InChI=1/C8H6N2O2S/c11-7(12)4-1-2-5-6(3-4)10-8(13)9-5/h1-3H,(H,11,12)(H2,9,10,13)

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 75-15-0 carbon disulfide 
• 619-05-6 3,4-diaminobenzoic acid 

Downstream Products

• 148720-14-3 2-methylthio-5-carboxybenzimidazole 
• 119445-15-7 2-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propyl-thio]benzimidazole-5-carboxylic acid 
• 117976-63-3 5-carboxy-2-[{4-(2-benzyloxy)ethoxy-3-methylpyridine-2-yl}methylthio]-1H-benzimidazole 
• 1252655-83-6 tert-butyl [(5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-benzimidazol-2-yl)sulfanyl]acetate 
• 1252655-85-8 [(5-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1H-benzimidazol-2-yl)sulfanyl]acetic acid 
• 1252655-81-4 5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-benzimidazole-2-thiol 

Relevant articles and documents

COMPOUNDS USEFUL AS ANTIBIOTIC TOLERANCE INHIBITORS

The disclosure provides compounds and pharmaceutical compositions of the compounds useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds and salts of general Formula VIII Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a patient, including Pseudomonas aeruginosa infections, are also provided by the disclosure.

Synthesis and biological activity of splitomicin analogs targeted at human NAD+-dependent histone deacetylases (sirtuins)

Small molecules interfering with posttranslational modification of histones are of interest as tools to study epigenetic regulation of gene transcription. Specifically, drugs that interfere with histone deacetylation could be useful to induce differentiation, growth arrest as well as apoptotic cell death in tumor cells. One class of histone deacetylases is known as sirtuins some of which (Saccharomyces cerevisiae Sir2) are for example inhibited by the lactone splitomicin leading to telomeric silencing in yeast. However, splitomicin is only a micromolar inhibitor of yeast Sir2 and does not inhibit human subtypes and the lactone is prone to hydrolytic ring opening. In preliminary SAR-studies, splitomicin analogs lacking this hydrolytically labile ring were described as inactive while the naphthalene moiety could successfully be replaced by smaller aromatic rings in a fragment-like dihydrocoumarin. Here we report the synthesis and biological activity of a series of hydrolytically stable analogs with activity against human SIRT1 and 2. These comparatively small compounds characterized by high ligand efficiency are used as a starting point toward the development of specific inhibitors of histone deacetylases from the class of sirtuins.

Cyclization of [(4- or 5-substituted-2-benzimidazolyl)thio]acetic acids. Isolation and identification of two possible isomers of substituted thiazolo[3,2-a]benzimidazol-3(2H)-one

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