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Synthesis and pharmacological evaluation of 5,6,7,8‐tetrahydro‐6‐[propyl[2‐(2‐thienyl)ethyl]amino]‐1,2‐naphthalenediol: A novel non‐selective dopamine‐receptor agonist
- Source :
- Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands Chemical Society, 112(2), 137-142. ELSEVIER SCIENCE BV
- Publication Year :
- 1993
-
Abstract
- Based on the hypothesis that simultaneous stimulation of dopamine-D1 and -D2 receptors could be beneficial for the treatment of Parkinson's disease7,13, we prepared 5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1,2-naphthalenediol (PTAT, 4), the diol analogue of N-0437 (3), as a potential mixed D1/D2-receptor agonist. The synthesis of 4 was carried out via a new strategy. The crucial step in this strategy was the conversion of 1-diazo-4-(2,3-dimethoxyphenyl)-2-butanone (15) to the key intermediate 5,6-dimethoxy-2-tetralone (9) via a rhodium(II)-acetate-catalysed cyclisation, followed by transformation under the influence of trifluoroacetic acid. Pharmacological evaluation of the dopaminergic properties of PTAT (4) revealed that this compound displays high affinity for both D1 and D2 receptors and has the same ability as DPAT (1), a mixed D1/D2-receptor agonist, to induce locomotor activity in mice rendered acutely akinetic with reserpine.
- Subjects :
- Agonist
STIMULATION
N-0437 [H-3] SCH 23390
medicine.drug_class
Stereochemistry
ENANTIOMERS
chemistry.chemical_compound
N-0437
Dopamine receptor D2
BINDING
medicine
Trifluoroacetic acid
D-1
[H-3] SPIPERONE
SCH-23390
POTENT
Dopaminergic
N-DISUBSTITUTED 2-AMINOTETRALINS
RESERPINE
STRIATAL DOPAMINE
General Chemistry
Reserpine
Ligand (biochemistry)
D2-RECEPTOR AGONIST
RHODIUM(II)-ACETATECATALYSED CYCLIZATION
chemistry
MIXED D1
Dopamine receptor
LIGAND
N,N-DISUBSTITUTED 2-AMINOTETRALINS
SKF 38393
medicine.drug
Subjects
Details
- Language :
- English
- ISSN :
- 01650513
- Volume :
- 112
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands Chemical Society
- Accession number :
- edsair.doi.dedup.....8053ce20a3a629b233e4976308682636