315-53-7Relevant articles and documents
Synthesis and β-adrenergic activities of R-fluoronaphthyloxypropanolamine
Adejare, Adeboye,Sciberras, Sophie S.
, p. 533 - 536 (1997)
Purpose. Many biogenic amines where an aromatic proton is substituted with fluorine have exhibited pharmacological properties that are dependent on the position of fluorine on the aromatic ring. For example, 6-fluoroepinephrine is selective for α-adrenergic receptors whereas the 2-fluoroisomer is selective for β-receptors. Aryloxypropanolamines are β-receptor agonists or antagonists, depending on the aryl group and its substituents. We therefore hypothesized that fluorine substitution on the aromatic ring could lead to significant biological effects in this class. A target with fluorine on naphthyl group of a known β-antagonist was chosen for investigation. Methods. Synthesis of the target compound began with fluoronaphthalene and involved introduction of 4-hydroxy group by Friedel-Crafts acylation followed by Baeyer Villiger oxidation. The side chain was introduced stereoselectively using the chiral synthon (2R)-glycidyl 3-nitrobenzenesulfonate, a Sharpless epoxidation technique. The epoxide was opened with t-butyl amine. HPLC methods were used to characterize %ee of the enantiomer. Results. The target compound was synthesized in several hundred milligram quantity, and in good yield and high enantiomeric excess, showing practicality of the synthetic scheme. It exhibited potent binding activities on β-adrenergic receptors, and was found to be two times selective for β2-receptors over β1. Conclusions. The current report demonstrates that aromatic fluorine substitution on β-adrenergic ligands can be achieved, and that such can be used to obtain binding selectivity between β receptors.
SelectfluorTMon a PolyHIPE Material as Regenerative and Reusable Polymer-Supported Electrophilic Fluorinating Agent
Kawada, Kosuke,Okano, Koji,Iskra, Jernej,Krajnc, Peter,Cahard, Dominique
supporting information, p. 584 - 589 (2017/02/23)
The first recyclable polymer-supported electrophilic fluorinating agent was prepared by reaction of molecular fluorine with the triethylenediamine motif that is grafted onto a poly(4-vinylbenzyl chloride-co-divinylbenzene) polyHIPE material. The resulting
OLIGOMER-ARYLOXY-SUBSTITUTED PROPANAMINE CONJUGATES
-
, (2016/11/17)
The invention relates to (among other things) oligomer- aryloxy-substituted propanamine conjugates and related compounds. A conjugate of the invention, when administered by any of a number of administration routes, exhibits advantages over un-conjugated aryloxy-substituted propanamine compounds.
