Adejare, Adeboye published the artcileSynthesis and β-adrenergic activities of R-fluoronaphthyloxypropanolamine, Recommanded Product: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Pharmaceutical Research (1997), 14(4), 533-536, database is CAplus.
Many biogenic amines where an aromatic proton is substituted with fluorine have exhibited pharmacol. 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. The authors therefore hypothesized that fluorine substitution on the aromatic ring could lead to significant biol. effects in this class. A target with fluorine on naphthyl group of a known β-antagonist was chosen for investigation. 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-Bu amine. HPLC methods were used to characterize %ee of the enantiomer. 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 two times selective for β2-receptors over β1. 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.
Pharmaceutical Research published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Recommanded Product: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.
Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics