6533b853fe1ef96bd12ac99c
RESEARCH PRODUCT
Syntheses of dopaminergic 1-cyclohexylmethyl-7,8-dioxygenated tetrahydroisoquinolines by selective heterogeneous tandem hydrogenation
Gregorio TorresDiego CortesAlmudena BermejoImmaculada AndreuMaria ValpuestaM. Carmen Ramírez De ArellanoNuria CabedoPhilippe ProtaisAbdeslam ChagraouiSalvador Gilsubject
TandemTetrahydroisoquinolineStereochemistryOrganic ChemistryDopaminergicRegioselectivityRing (chemistry)Biochemistrychemistry.chemical_compoundchemistryDopamine receptorTHIQDrug DiscoverymedicineBinding sitemedicine.drugdescription
Abstract 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-12-01 | Tetrahedron |