1401067-58-0

Upstream product

• 22509-74-6 N-ethoxycarbonylphthalimide 
• 32464-55-4 2-(4,4-diethoxybutyl)isoindoline-1,3-dione 

Downstream Products

• 1401067-72-8 2-(4-((tert-butyldimethylsilyl)oxy)-4-(2-nitrophenyl)butyl)-isoindoline-1,3-dione 
• 1401067-59-1 4-((tert-butyldimethylsilyl)oxy)-(2-nitrophenyl)butan-2-amine 
• 1401067-68-2 (4R)-N-(3-((4-((tert-butyldimethylsilyl)oxy)-4-(2-nitrophenyl)butyl)amine)-3-oxo-propyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide 
• 1401067-69-3 (4R)-N-(3-((4-(2-aminophenyl)-4-((tert-butyldimethylsilyl)oxy)-butyl)amino)-3-oxopropyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide 
• 1401067-60-4 N-(4-((tert-butyldimethylsilyl)oxy)-4-(2-nitrophenyl)acetamide) 
• 1401067-61-5 N-(4-hydroxy-4-(2-nitrophenyl)butyl)acetamide 
• 1401067-62-6 N-(4-(2-nitrophenyl)-4-oxobutyl)acetamide 
• 1401067-54-6 (R)-2,4-dihydroxy-3,3-dimethyl-N-(3-((4-(2-nitrophenyl)-4-oxobutyl)amino)-3-oxopropyl)-butanamide 
• 1401067-56-8 (2R)-2,4-dihydroxy-N-(3-((4-hydroxy-4-(2-nitrophenyl)butyl)amino)-3-oxopropyl)-3,3-dimethylbutanamide 
• 1401067-57-9 (2R)-N-(3-((4-(2-aminophenyl)-4-hydroxybutyl)amino)-3-oxopropyl)-2,4-dihydroxy-3,3-dimethylbutanamide 
• 1621071-27-9 1-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)-3-(4-hydroxy-4-(2-nitrophenyl)butyl)thiourea 
• 1621071-26-8 N-(4-hydroxy-4-(2-nitrophenyl)butyl)-6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanamide 
• 1621071-25-7 N-(4-hydroxy-4-(2-nitrophenyl)butyl)-3-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)propanamide 
• 1621071-24-6 4-((7-mitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)-1-(2-nitrophenyl)butan-1-ol 

Relevant academic research and scientific papers

From in vitro to in cellulo: Structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa

Recent studies have shown that compounds based on a (2-nitrophenyl)methanol scaffold are promising inhibitors of PqsD, a key enzyme of signal molecule biosynthesis in the cell-to-cell communication of Pseudomonas aeruginosa. The most promising molecule displayed anti-biofilm activity and a tight-binding mode of action. Herein, we report on the convenient synthesis and biochemical evaluation of a comprehensive series of (2-nitrophenyl)methanol derivatives. The in vitro potency of these inhibitors against recombinant PqsD as well as the effect of selected compounds on the production of the signal molecules HHQ and PQS in P. aeruginosa were examined. The gathered data allowed the establishment of a structure-activity relationship, which was used to design fluorescent inhibitors, and finally, led to the discovery of (2-nitrophenyl)methanol derivatives with improved in cellulo efficacy providing new perspectives towards the application of PqsD inhibitors as anti-infectives. This journal is the Partner Organisations 2014.

Validation of PqsD as an anti-biofilm target in pseudomonas aeruginosa by development of small-molecule inhibitors

2-Heptyl-4-hydroxyquinoline (HHQ) and Pseudomonas quinolone signal (PQS) are involved in the regulation of virulence factor production and biofilm formation in Pseudomonas aeruginosa. PqsD is a key enzyme in the biosynthesis of these signal molecules. Using a ligand-based approach, we have identified the first class of PqsD inhibitors. Simplification and rigidization led to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in P. aeruginosa. This validates PqsD as a target for the development of anti-infectives.