517906-95-5Relevant academic research and scientific papers
Syntheses of dopaminergic 1-cyclohexylmethyl-7,8-dioxygenated tetrahydroisoquinolines by selective heterogeneous tandem hydrogenation
Andreu, Inmaculada,Cabedo, Nuria,Torres, Gregorio,Chagraoui, Abdeslam,Ramírez de Arellano, M. Carmen,Gil, Salvador,Bermejo, Almudena,Valpuesta, María,Protais, Philippe,Cortes, Diego
, p. 10173 - 10179 (2007/10/03)
We describe the preparation in a 'one-pot' sequence 1-cyclohexylmethyl 7,8-dioxygenated tetrahydroisoquinoline, substituted and unsubstituted in the C ring by application of the Photo-Fries transposition, followed by a tandem reduction-cyclization and further reduction. Indeed, we have accomplished for the first time regioselective hydrogenation of the benzylic ring of the tetrahydroisoquinoline systems. All 1-cyclohexylmethyl THIQ synthesized were able to displace D2 dopamine receptor from its specific binding site in rat striatal membranes, while the N-methylated derivatives showed also affinity for D1 dopamine receptors.
