845543-39-7

Basic information

• Product Name: 2-Oxazolidinone, 3-[3-(3,5-difluorophenyl)-1-oxopropyl]-4-(1-methylethyl)-, (4S)-
• CAS NO: 845543-39-7
• Molecular Formula: C15H17F2NO3
• Molecular Weight: 297.302
• Mol File: 845543-39-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3-[3-(3,5-difluorophenyl)-1-oxopropyl]-4-(1-methylethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3-[3-(3,5-difluorophenyl)-1-oxopropyl]-4-(1-methylethyl)-, (4S)-(845543-39-7)
• EPA Substance Registry System: 2-Oxazolidinone, 3-[3-(3,5-difluorophenyl)-1-oxopropyl]-4-(1-methylethyl)-, (4S)-(845543-39-7)

Safety Data

• Hazardous Substances Data: 845543-39-7(Hazardous Substances Data)

Upstream product

• 95333-92-9 3-(3,5-difluorophenyl)propionyl chloride 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 84315-23-1 3,5-difluorocinnamic acid 
• 84315-24-2 3-(3,5-difluorophenyl)propionic acid 

Downstream Products

• 845543-62-6 C₂₅H₃₄F₂N₂O₆ 
• 845543-64-8 C₂₆H₃₁F₂NO₅ 
• 845543-63-7 C₁₉H₂₅F₂NO₅ 

Relevant articles and documents

A fluorine scan of non-peptidic inhibitors of neprilysin: Fluorophobic and fluorophilic regions in an enzyme active site

This article describes the synthesis and in vitro biological affinities of (poly)fluorinated neprilysin inhibitors. Two series of inhibitors with F-substitution of the central benzimidazole platform of the ligands and the benzylic vector to fill the S1' pocket of NEP were investigated. The S1' pocket was found to be highly fluorophobic, and F-substitution led to significantly decreased binding affinities of inhibitors. This result is explained by electrostatically unfavorable close contacts of organic fluorine with the negatively polarized π-surfaces of surrounding aromatic amino acid side chains. In contrast, the protein environment around the benzimidazole platform, with three electropositive guanidinium side chains of Arg residues, was found to provide a fluorophilic environment. Overall, the data support that organic fluorine, with its high negative charge density prefers to orient into electropositive regions of receptor sites. pKa measurements of fluorinated ligands provided several simple patterns for the prediction of pKa values of benzimidazoles, important building blocks in medicinal chemistry.

CYCLIC AMINE BACE-1 INHIBITORS HAVING A BENZAMIDE SUBSTITUENT

Disclosed are compounds of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein R is-C(O)-N(R27)(R28) or and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula I. Also disclosed are methods of treating cognitive or neurodegenerative diseases such as Alzheimer’s disease. Also disclosed are pharmaceutical compositions and methods of treating cognitive or neurodegenerative diseases comprising the compounds of formula I in combination with a β-secretase inhibitor other than those of formula I, an HMG-CoA reductase inhibitor, a gamma-secretase inhibitor, a non-steroidal anti-inflammatory agent, and N-methyl-D-aspartate receptor antagonist, a cholinesterase inhibitor or an anti-amyloid antibody.