103438-92-2Relevant articles and documents
Syntheses of 6-fluoro-meta-tyrosine and of its metabolites
Konkel, Jamie T,Fan, Junfa,Jayachandran,Kirk, Kenneth L
, p. 27 - 32 (2007/10/03)
6-Fluoro-meta-tyrosine (1) was prepared from 2-fluoro-5-hydroxybenzaldehyde (6) based on an Erlenmeyer-Pl?chl azlactone strategy. Products of expected metabolism of the amino acid, including 6-fluoro-meta-tyramine (2) and its O-sulfate conjugate (3), (2-f
Synthesis of high-specific-radioactivity 4- and 6-[18F]fluorometaraminol- PET tracers for the adrenergic nervous system of the heart
Langer, Oliver,Dollé, Frédéric,Valette, Héric,Halldin, Christer,Vaufrey, Fran?oise,Fuseau, Chantal,Coulon, Christine,Ottaviani, Michéle,N?gren, Kjell,Bottlaender, Michel,Maziére, Bernard,Crouzel, Christian
, p. 677 - 694 (2007/10/03)
Fluorine-18 (t12:109.8min)-labeled analogues of metaraminol, 4-[18F]FMR ((1R,2S)-2-amino-1-(4-[18F]fluoro-3-hydroxy phenyl)-1-propanol) and 6-[18F]FMR ((1R,2S)-2-amino-1-(2-[18F]fluoro-5-hydroxyphenyl)-1-propanol), were synthesized as new positron-emission-tomography (PET) tracers for mapping cardiac adrenergic nerve terminals. Copyright
tert-BUTYLDIMETHYLSILYL ETHERS OF PHENOLS: THEIR ONE-STEP CONVERSION TO BENZYL OR METHYL ETHERS AND UTILITY IN REGIOSELECTIVE ortho LITHIATION
Sinhababu, Achintya K.,Kawase, Masami,Borchardt, Ronald T.
, p. 4139 - 4142 (2007/10/02)
A new method for the one-step conversion of tert-butyldimethylsilyl ethers of phenols to benzyl or methyl ethers and the blocking effect of the tert-butyldimethylsilyloxy group in regioselective ortho lithiation are described.
Synthesis and Adrenergic Activity of Ring-Fluorinated Phenylephrines
Kirk, Kenneth L.,Olubajo, Olarangbe,Buchhold, Konstantin,Lewandowski, Gail A.,Gusovsky, Fabian,et al.
, p. 1982 - 1988 (2007/10/02)
2-Fluoro-, 4-fluoro-, and 6-fluorophenylephrine (6-FPE) were synthesized from the corresponding fluorinated 3-hydroxybenzaldehydes.New routes to 2-fluoro- and 6-fluoro-3-hydroxybenzaldehydes were developed based on regioselective lithiation of 2- and 4-fluorobenzene ortho to fluorine.As with norepinephrine and isoproterenol analogues, the adrenergic properties of phenylephrine were markedly altered by ring fluorination.The order of potency of the fluoro analogues as α1-adrenergic agonists in the stimulation of contraction of aorticstrips and of phosphatidylinositol turnover and potentiation of cyclic AMP accumulation in guinea pig synaptoneurosomes was 6-FPE > PE > 4-FPE > 2-FPE.The same pattern was observed for the displacement of radioligands specific for α1- and α2-adrenergic receptors on brain membranes.The order of potency for the displacement of 3H>dihydroalprenolol, a β-specific adrenergic ligand from brain membranes, was 2-FPE > 4-FPE = PE >> 6-FPE. 6-FPE was much more selective for α-adrenergic receptors compared to β-receptors than was phenylephrine.A rationale for the observed fluorine-induced alterations in potency and selectivity of the FPEs for α- and β-adrenergic systems is presented based on fluorine-induced conformations due to electrostatic repulsion of fluorine and the benzyl hydroxyl group.
