158040-76-7

Basic information

• Product Name: 2-(2-HYDROXY-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID
• Synonyms: 2-(2-HYDROXY-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID;2-(2-Hydroxyphenyl)-3H-benzimidazole-5-carboxylic acid;2-(2-Hydroxy-phenyl)-1H-benzimidazole-5-carboxylic acid;2-(2-Hydroxyphenyl)-1H-benzimidazole-6-carboxylic acid;2-(2-Hydroxyphenyl)-3H-benzimidazole-5-carboxylic acid, 6-Carboxy-2-(2-hydroxyphenyl)-1H-benzimidazole, 2-(6-Carboxy-1H-benzimidazol-2-yl)phenol;2-(2-hydroxyphenyl)-1H-1,3-benzodiazole-6-carboxylic acid
• CAS NO: 158040-76-7
• Molecular Formula: C₁₄H₁₀N₂O₃
• Molecular Weight: 254.24
• Mol File: 158040-76-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 575.6°Cat760mmHg
• Flash Point: 301.9°C
• Appearance: /
• Density: 1.483g/cm³
• Vapor Pressure: 4.32E-14mmHg at 25°C
• Refractive Index: 1.753
• CAS DataBase Reference: 2-(2-HYDROXY-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-HYDROXY-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(158040-76-7)
• EPA Substance Registry System: 2-(2-HYDROXY-PHENYL)-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(158040-76-7)

Safety Data

• Hazardous Substances Data: 158040-76-7(Hazardous Substances Data)

Usage

Synonym

PHPC

Chemical class

Benzoimidazole derivatives

Molecular weight

266.24 g/mol

Pharmaceutical potential

Anti-inflammatory and antioxidant properties

Mechanism of action

Inhibition of proinflammatory mediators and oxidative stress

Status in research

Promising candidate for new drug development

Area of interest

Medicinal chemistry

InChI:InChI=1/C14H10N2O3/c17-12-4-2-1-3-9(12)13-15-10-6-5-8(14(18)19)7-11(10)16-13/h1-7,17H,(H,15,16)(H,18,19)

Upstream product

• 90-02-8 salicylaldehyde 
• 619-05-6 3,4-diaminobenzoic acid 

Relevant articles and documents

Novel Tacrine-Hydroxyphenylbenzimidazole hybrids as potential multitarget drug candidates for Alzheimer's disease

Alzheimer's disease (AD) is a severe age-dependent neurodegenerative disorder affecting millions of people, with no cure so far. The current treatments only achieve some temporary amelioration of the cognition symptoms. The main characteristics of the patient brains include the accumulation of amyloid plaques and neurofibrillary tangles (outside and inside the neurons) but also cholinergic deficit, increased oxidative stress and dyshomeostasis of transition metal ions. Considering the multi-factorial nature of AD, we report herein the development of a novel series of potential multi-target directed drugs which, besides the capacity to recover the cholinergic neurons, can also target other AD hallmarks. The novel series of tacrine-hydroxyphenylbenzimidazole (TAC-BIM) hybrid molecules has been designed, synthesized and studied for their multiple biological activities. These agents showed improved AChE inhibitory activity (IC50 in nanomolar range), as compared with the single drug tacrine (TAC), and also a high inhibition of self-induced- and Cu-induced-Aβ aggregation (up to 75%). They also present moderate radical scavenging activity and metal chelating ability. In addition, neuroprotective studies revealed that all these tested compounds are able to inhibit the neurotoxicity induced by Aβ and Fe/AscH(-) in neuronal cells. Hence, for this set of hybrids, structure-activity relationships are discussed and finally it is highlighted their real promising interest as potential anti-AD drugs.