82138-56-5

Basic information

• Product Name: 3-(6-CHLORO-1H-BENZOIMIDAZOL-2-YL)-PROPIONIC ACID
• Synonyms: 3-(6-CHLORO-1H-BENZOIMIDAZOL-2-YL)-PROPIONIC ACID;ASINEX-REAG BAS 10145510;3-(5-chloro-1H-benzimidazol-2-yl)propanoic acid
• CAS NO: 82138-56-5
• Molecular Formula: C10H9ClN2O2
• Molecular Weight: 224.64
• Product Categories: pharmacetical
• Mol File: 82138-56-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(6-CHLORO-1H-BENZOIMIDAZOL-2-YL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(6-CHLORO-1H-BENZOIMIDAZOL-2-YL)-PROPIONIC ACID(82138-56-5)
• EPA Substance Registry System: 3-(6-CHLORO-1H-BENZOIMIDAZOL-2-YL)-PROPIONIC ACID(82138-56-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 82138-56-5(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 95-83-0 4-Chloro-1,2-phenylenediamine 

Relevant articles and documents

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.

Synthesis of some hydroxamic acid derivatives of benzimidazole and their antibacterial and antifungal activities

A number of 1H-benzimidazole-2-propanoic acid derivatives have been synthesized by Phillips method, and their antibacterial and antifungal activities have been tested. The chemical structures of the synthesized compounds were elucidated by spectroscopic (IR, NMR, mass) and elementary analysis. Investigation of antimicrobial activity of the compounds was done by agar dilution technique using bacteria (Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Mycobacterium smegmatis ATCC 607) and yeast-like fungi (Candida albicans, Candida tropicalis, Candida pseudotropicalis, Candida kruzei, Candida globrata). Among the compounds tested N-hydroxy-3-(1H-benzimidazol-2-yl)-propionamide (Compound 6) showed considerable activity against both Candida albicans and Candida tropicalis.