21541-32-2

Usage

Class of Compound

Benzimidazole

Structure

Benzene ring fused to an imidazole ring
Thione group attached at position 2
Acetyl group at position 1
Dihydro group at position 3

Applications

Organic synthesis
Pharmaceutical research

Usage

Building block for drug development
Active pharmaceutical ingredient

Potential Applications

Treatment of various diseases and medical conditions

Properties

Chemical properties: Reactivity due to functional groups
Biological properties: Potential therapeutic effects
Physical properties: Melting point, solubility, etc.

Behaviors

Reactivity in different reaction conditions
Pharmacological behaviors in biological systems

Upstream product

• 3042-01-1 thiazolo[3,2-a]benzimidazol-3(2H)-one 
• 108-24-7 acetic anhydride 
• 134469-07-1 Benzimidazol-2-thiol 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 56029-79-9 N,N'-Diacetyl-benzimidazolin-2-thion 
• 137213-71-9 (triphenylmethyl)sulfanylbenzimidazole 
• 137213-76-4 1-(2-Tritylsulfanyl-benzoimidazol-1-yl)-ethanone 

Downstream Products

• 878991-07-2 C₂₁H₁₉N₅O₂S₂ 
• 51290-77-8 2-(benzylthio)-1H-benzo[d]imidazole 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 

Relevant academic research and scientific papers

Synthesis and crystal structures of benzimidazole-2-thione derivatives by alkylation reactions

Alkylated, benzylated and bromoalkylated benzimidazole-thione that intramolecularly heterocyclized to 3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazole were synthesized. The chemical structure of the synthesized product was characterized by Infra Red, 1H-NMR, 13C-NMR, and Mass spectroscopy. Furthermore, the molecular structures of 8 and 9 were confirmed by X-ray single crystallography in different space groups, Pbca and P21/c, respectively.

Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase

Bacterial hyaluronan lyases (Hyal) degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread. Hyal inhibitors may serve as tools to study the role of the enzyme, its substrates and products in the course of bacterial infections. Moreover, such enzyme inhibitors are potential candidates for antibacterial combination therapy. Based on crystal structures of Streptococcus pneumoniae Hyal in complex with a hexasaccharide substrate and with different inhibitors, 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones were derived as new leads for the inhibition of Streptococcus agalactiae strain 4755 Hyal. Structure-based optimization led to N-(3-phenylpropionyl)benzoxazole-2-thione, one of the most potent compounds known to date (IC50 values: 24 μM at pH 7.4, 15 μM at pH 5). Among the 27 new derivatives, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5. The results support a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch.

Inhibitors of the salicylate synthase (Mbti) from Mycobacterium tuberculosis discovered by high-throughput screening

A simple steady-state kinetic high-throughput assay was developed for the salicylate synthase MbtI from Mycobacterium tuberculosis, which catalyzes the first committed step of mycobactin biosynthesis. The mycobactins are small-molecule iron chelators produced by M. tuberculosis, and their biosynthesis has been identified as a promising target for the development of new antitubercular agents. The assay was miniaturized to a 384-well plate format and high-throughput screening was performed at the National Screening Laboratory for the Regional Centers of Excellence in Biodefense and Emerging Infectious Diseases (NSRB). Three classes of compounds were identified comprising the benzisothiazolones (class I), diarylsulfones (class II), and benzimidazole-2-thiones (class III). Each of these compound series was further pursued to investigate their biochemical mechanism and structure-activity relationships. Benzimidazole-2-thione 4 emerged as the most promising inhibitor owing to its potent reversible inhibition.

Thiosulfonate Derivatives of Benzimidazole

S-Esters of thiosulfonic acids containing benzimidazol-2-yl, 1-acetylbenzimidazol-2-yl and 2-methoxycarbamoylbenzimidazol-6-yl substituents from the side of the oxidized and sulfide sulfur were synthesized. Various methods of preparation of S-esters of th

Synthesis of N-substituted benzimidazole-2-thiones

General methods were developed for N-substitution of benzimidazoline-2-thione with alkyl, alkenyl, alkynyl and acyl groups using S-tritylation as a protecting reaction.

Electrochemical Behaviour of Some Thiazolobenzimidazol-3(2H)-one Derivatives. Part 1. Electroreduction of a Series of 2-Arylazothiazolobenzimidazol-3(2H)-ones

The electrochemical reduction of a series of 2-arylazothiazolobenzimidazol-3(2H)-ones has been investigated.A mechanism for the electrode process covering a wide range of pH values is proposed, discussed, and clarified via model compounds, polarographic analysis, pKa determination, and interpretation of Hammett's ?/E1/2 relations.Large-scale preparative electrolysis of the title and model compounds was carried out and the products were isolated and identified.

Synthesis and Spectral Studies of 2-Mercaptobenzimidazole Derivatives.I.

The syntheses of some 2-mercaptobenzimidazole (I) derivatives have been described.While preparing such compounds it has been observed that I reacts predominantly as the thione under anhydrous reaction conditions, and as the thiol in the presence of an alkali.Structures of all of the nine compounds have been established with the help of spectral methods including 13C nmr spectroscopy of the two compounds ( II and III ).