206982-69-6

Basic information

• Product Name: 2-(4-CHLOROSTYRYL)-1H-1,3-BENZIMIDAZOLE
• Synonyms: 2-[(E)-2-(4-CHLOROPHENYL)ETHENYL]-1H-BENZIMIDAZOLE;2-(4-CHLOROSTYRYL)-1H-1,3-BENZIMIDAZOLE;2-[(E)-2-(4-chlorophenyl)ethenyl]-1H-1,3-benzodiazole
• CAS NO: 206982-69-6
• Molecular Formula: C₁₅H₁₁ClN₂
• Molecular Weight: 254.71
• Mol File: 206982-69-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-CHLOROSTYRYL)-1H-1,3-BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLOROSTYRYL)-1H-1,3-BENZIMIDAZOLE(206982-69-6)
• EPA Substance Registry System: 2-(4-CHLOROSTYRYL)-1H-1,3-BENZIMIDAZOLE(206982-69-6)

Safety Data

• Hazardous Substances Data: 206982-69-6(Hazardous Substances Data)

Usage

Molecular structure

Contains a benzimidazole ring and a chlorostyryl group.

Type of compound

Fluorescent compound.

Potential use

Biomedical imaging, fluorescent probe in biological and medical research.

Studied for

Anti-cancer and anti-inflammatory properties, ability to bind to certain enzymes and receptors in the body.

Value

Unique fluorescent and chemical properties, useful for studying molecular interactions and developing new therapeutic agents.

Upstream product

• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 615-28-1 o-phenylenediamine dihydrochloride 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 104-88-1 4-chlorobenzaldehyde 
• 74710-09-1 o-phenylenediamine sulphate 
• 95-54-5 1,2-diamino-benzene 
• 89812-53-3 (E)-5-(4-chlorophenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one 

Downstream Products

• 259743-62-9 (E)-2-(4-chlorostyryl)-1-methyl-1H-benzo[d]imidazole 
• 1620567-39-6 C₂₂H₁₆Cl₃N₃ 
• 1620567-15-8 (R)-2-(3',5'-dichlorophenyl)-3-(4'-chlorophenyl)-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2-c]pyrimidin-4-ol 
• 1620567-57-8 C₂₂H₁₆Cl₃N₃O 

Relevant articles and documents

α-Aroylidineketene dithioacetal chemistry: CuI catalyzed synthesis of 2-styryl benzimidazoles enroute to regioselective hydrothiolation

Abstract Reactivity of α-aroylidineketene dithioacetals 2 was investigated to synthesize novel 2-styrylbenzimidazole derivatives 4 and their hydrothiolated product 2-(2-(methylthio)-2-arylethyl)-1H-benzo[d]imidazoles 5 has been reported. Compounds 4 and 5

Design, synthesis and docking studies of some novel (R)-2-(4′- chlorophenyl)-3-(4′-nitrophenyl)-1,2,3,5-tetrahydrobenzo[4,5] imidazo [1,2-c]pyrimidin-4-ol derivatives as antitubercular agents

Filamenting temperature-sensitive mutant (FtsZ) is a novel target for the treatment of tuberculosis. A series of (R)-2-(4′-chlorophenyl)-3- (4′-nitrophenyl)-1,2,3,5-tetrahydrobenzo[4,5] imidazo[1,2-c]pyrimidin-4-ol derivatives were designed and docked on the FtsZ protein crystal structure (PDB Id: 1RLU, resolution 2.08 ?). Compound 7t showed the highest docking score and H-bond interaction with Arg140 and Gly19. Our strategy for synthesis of (R)-2-(4′-chlorophenyl)-3-(4′-nitrophenyl)-1,2,3,5- tetrahydrobenzo[4,5]imidazo[1,2-c]pyrimidin-4-ol derivatives from o-phenylenediamine as illustrated in scheme. All the synthesized compounds were characterized by FTIR, Mass spectra, 1H NMR, 13C NMR, elemental analysis and purity was confirmed by HPLC and LCMS. Compound 7g was also confirmed by single crystal X-ray analysis. The in silico results are also validated with in vitro antitubercular activity of compound 7t. Compound 7b exhibited in vitro antitubercular activity 3.13 μg/mL and 4.7 μg/mL whereas compound 7t exhibited in vitro antitubercular activity 6.25 μg/mL and 9.4 μg/mL using GAST/Fe medium after week 1 and week 2 respectively against Mycobacterium tuberculosis H37Rv. Medium 7H9/ADC/Tween was found to be very less effective for in vitro antitubercular activity of all the benzimidazole derivatives. Assays for in vitro cytotoxicity against VERO cells of all the synthesized compounds was found to be very less cytotoxic.

Condensation of o-phenylenediamine with cinnamic acids

Condensation of o-phenylenediamine sulfate with cinnamic acids in refluxing ethylene glycol yielded the corresponding 2-styrylbenzimidazoles in excellent yields.