46083-40-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(1R,2S)-2-amino-1-(4-fluorophenyl)propanol is used as an intermediate in the synthesis of pharmaceuticals for its ability to selectively bind to and activate certain receptors in the body.
Used in Chiral Ligand and Catalyst Production:
(1R,2S)-2-amino-1-(4-fluorophenyl)propanol is used as a precursor in the production of chiral ligands and catalysts due to its chiral nature, which is essential for asymmetric synthesis and enantiopure drug manufacturing.

Upstream product

• 322-27-0 N-[(1RS,2SR)-2-(4-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-acetamide 
• 568550-19-6 (S)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanone 
• 456-03-1 1-(4-fluorophenyl)propan-1-one 
• 345-94-8 2-bromo-1-(4-fluorophenyl)propan-1-one 
• 211242-52-3 2-N,N-dibenzylamino-1-(4-fluorophenyl)-1-propanone 

Downstream Products

• 502850-13-7 (2RS,3S)-2-(4-fluorophenyl)-3-methylaziridine 
• 502850-17-1 (1R,2S)-1,2-diamino-1-(4-fluorophenyl)propane 

Relevant academic research and scientific papers

Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors

The discovery and optimization of Δ-5 desaturase (D5D) inhibitors are described. Investigation of the 1,3-oxazolidin-2-one scaffold was inspired by a pharmacophore model constructed from the common features of several hit compounds, resulting in the identification of 3,5-diphenyl-1,3-oxazolidin-2-one 5h as a novel lead showing potent in vitro activity. Subsequent optimization focused on the modification of two metabolic sites, which provided (4S,5S)-5i, a derivative with improved metabolic stability. Moreover, adding a substituent into the upper phenyl moiety further enhanced the intrinsic activity, which led to the discovery of 5-[(4S,5S)-5-(4fluorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]benzene-1,3-dicarbonitrile (4S,5S)-5n, endowed with excellent D5D binding affinity, cellular activity, and high oral bioavailability in a mouse. It exhibited robust in vivo hepatic arachidonic acid/dihomo-γ-linolenic acid ratio reduction (a target engagement marker) in an atherosclerosis mouse model. Finally, an asymmetric synthetic procedure for this compound was established.

Synthesis and antitumor activity of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)propane]dichloroplatinum(II) complexes.

Enantiomerically pure 1, 2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R, 2S)- and (1S, 2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by (1)H NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K(2)PtCl(4). The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl(2) were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl(2) produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl(2) even in a concentration of 1 microM. The (1S, 2R)- and (1R, 2S)-configurated complexes were far less active (SS > RR > RS = SR) and comparable in this respect with the standard cisplatin.