Chemistry:Flestolol

From HandWiki
Flestolol
Flestolol.svg
Names
IUPAC name
3-{[1-(Carbamoylamino)-2-methyl-2-propanyl]amino}-2-hydroxypropyl 2-fluorobenzoate
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
Properties
C15H22FN3O4
Molar mass 327.356 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Flestolol is a short-acting beta adrenergic receptor antagonist.[1]

Synthesis

Flestolol synthesis:[2]

Acylation of glycidol (2) with the acid chloride 1 produces the ester 3. Reaction of that intermediate with amine 4, obtained by reaction of 1,1-dimethylethylenediamine with urea, gives flestolol (5).

References

  1. Quon, CY; Stampfli, HF (1993). "Biochemical characterization of flestolol esterase". Research communications in chemical pathology and pharmacology 81 (3): 309–22. PMID 8235065. 
  2. Kam, Sheung Tsam; Matier, William L.; Mai, Khuong X.; Barcelon-Yang, Cynthia; Borgman, Robert J.; O'Donnell, John P.; Stampfli, Herman F.; Sum, Check Y. et al. (1984). "[(Arylcarbonyl)oxy]propanolamines. 1. Novel .beta.-blockers with ultrashort duration of action". Journal of Medicinal Chemistry 27 (8): 1007. doi:10.1021/jm00374a013. PMID 6146718.