75626-15-2Relevant articles and documents
Synthesis of fluorodopamines: Effect of aryl fluoro substituents on affinities for adrenergic and dopaminergic receptors
Nie, Jun-Ying,Shi, Dan,Daly, John W.,Kirk, Kenneth L.
, p. 318 - 332 (2007/10/03)
Monofluorine-substituted dopamines (1b-d) have been prepared previously. Synthetic routes to di- and trifluorinated dopamines (1e-h) were based on side chain elaboration of precursor fluorinated veratraldehydes. Binding data indicate that a 6-fluoro substituent decreases affinity at D1-, D2-, D3- and D4-dopamine receptors with the reduction (14-fold) being greatest at the D2-dopamine receptor. A 2-fluoro or 5-fluoro substituent had little or no effect. Additional 2- and/or 5-fluoro substituents further reduced affinity of 6-fluorodopamine for dopamine receptors. At adrenergic receptors, mono-fluoro substituents had only modest (2-fold or less) effects on affinity, while 2,6-di-, and 5,6-difluoro substitution modestly decreased affinity. 2,5,6-Trifluorodopamine had very low affinity.