Flestolol

Flestolol
Names
	IUPAC name 3-{[1-(Carbamoylamino)-2-methyl-2-propanyl]amino}-2-hydroxypropyl 2-fluorobenzoate
Identifiers
CAS Number	87721-62-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	50465;
KEGG	D04190;
PubChem CID	55885;
UNII	LI02075E1W ;
CompTox Dashboard (EPA)	DTXSID60868981 ;
	InChI InChI=1S/C15H22FN3O4/c1-15(2,9-18-14(17)22)19-7-10(20)8-23-13(21)11-5-3-4-6-12(11)16/h3-6,10,19-20H,7-9H2,1-2H3,(H3,17,18,22) Key: ZPLOQFLCMVIWRY-UHFFFAOYSA-N;
	SMILES CC(C)(CNC(=O)N)NCC(COC(=O)C1=CC=CC=C1F)O;
Properties
Chemical formula	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

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

Synthesis

Acylation of acid chloride 2-Fluorobenzoyl chloride [393-52-2] (1) with glycidol (2) produces the ester 2,3-Epoxypropyl 2-Fluorobenzoate [85515-51-1] (3). Reaction of that intermediate with amine (2-Amino-2-methyl-propyl)-urea [87484-83-1] (4) obtained by reaction of 1,1-dimethylethylenediamine with urea, gives flestolol (5).

References

^ Quon, CY; Stampfli, HF (1993). "Biochemical characterization of flestolol esterase". Research communications in chemical pathology and pharmacology. 81 (3): 309–22. PMID 8235065.
^ Day, BW; Pento, JT; ACC-9089. Drugs Fut 1985, 10, 6, 447.
^ 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.; Anderson, William G. (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.
^ Agustin Escobar, Dietmar M. Wagenknecht, Abu S. Alam, WO1985004581 (1985 to American Hospital Supply Corporation).

[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] Day, BW; Pento, JT; ACC-9089. Drugs Fut 1985, 10, 6, 447.

[3] 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.; Anderson, William G. (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.

[4] Agustin Escobar, Dietmar M. Wagenknecht, Abu S. Alam, WO1985004581 (1985 to American Hospital Supply Corporation).

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