1426396-71-5

Basic information

• Product Name: N-(4-bromo-3-(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamine
• Synonyms: N-(4-bromo-3-(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamine
• CAS NO: 1426396-71-5
• Molecular Weight: 366.565
• Mol File: 1426396-71-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(4-bromo-3-(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-bromo-3-(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamine(1426396-71-5)
• EPA Substance Registry System: N-(4-bromo-3-(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamine(1426396-71-5)

Safety Data

• Hazardous Substances Data: 1426396-71-5(Hazardous Substances Data)

Upstream product

• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 393-36-2 4-bromo-3-(trifluoromethyl)aniline 

Relevant articles and documents

Structure-activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling

A series of salicylanilides was synthesized based on a high-throughput screening hit against Mycobacterium tuberculosis. A free phenolic hydroxyl on the salicylic acid moeity is required for activity, and the structure-activity relationship of the aniline ring is largely driven by the presence of electron withdrawing groups. We synthesized 94 analogs exploring substitutions of both rings and the linker region in this series and we have identified multiple compounds with low micromolar potency. Unfortunately, cytotoxicity in a murine macrophage cell line trends with antimicrobial activity, suggesting a similar mechanism of action. We propose that salicylanilides function as proton shuttles that kill cells by destroying the cellular proton gradient, limiting their utility as potential therapeutics.