Facile synthesis of octahydrobenzo[h]isoquinolines: novel and highly potent D1 dopamine agonists.

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Bonner LA, Chemel BR, Watts VJ, Nichols DE

Facile synthesis of octahydrobenzo[h]isoquinolines: novel and highly potent D1 dopamine agonists.

Bioorg Med Chem. 2010 Sep 15;18(18):6763-70. doi: 10.1016/j.bmc.2010.07.052. Epub 2010 Jul 27.

PubMed ID

20709559 [ View in PubMed

]

Abstract

The octahydrobenzo[h]isoquinoline scaffold is of interest as a conformationally-restricted phenethylamine that may be useful for constructing biologically active products. Surprisingly, however, no tractable synthesis of this ring system has been reported. We now describe a facile method for obtaining this framework, and illustrate that our approach is easily amenable to substitutions at the 5-position. Importantly, we demonstrate that the 7,8-dihydroxy-5-phenyl-substituted ligand is an extremely potent, high-affinity, full D1 dopamine receptor-selective agonist.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Dopamine	Dopamine D1 receptor	EC 50 (nM)	20	N/A	N/A	Details