Lisa A Bonner1, Benjamin R Chemel, Val J Watts, David E Nichols. 1. Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, Purdue University, 575 Stadium Mall Drive, West Lafayette, IN 47907, United States.
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. Copyright (c) 2010 Elsevier Ltd. All rights reserved.
The octahydrobenzo[h]isoquinoline scaffold is of interest as a conformationally-restricted n class="Chemical">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 D1dopamine receptor-selective agonist. Copyright (c) 2010 Elsevier Ltd. All rights reserved.
Authors: J R Taylor; M S Lawrence; D E Redmond; J D Elsworth; R H Roth; D E Nichols; R B Mailman Journal: Eur J Pharmacol Date: 1991-07-09 Impact factor: 4.432
Authors: Alia H Clark; John D McCorvy; Jason M Conley; Whitney K Williams; Markondaiah Bekkam; Val J Watts; David E Nichols Journal: Bioorg Med Chem Date: 2012-09-08 Impact factor: 3.641
Authors: Lisa A Bonner; Uros Laban; Benjamin R Chemel; Jose I Juncosa; Markus A Lill; Val J Watts; David E Nichols Journal: ChemMedChem Date: 2011-04-28 Impact factor: 3.466