5,7-Dihydroxy-2-aminotetralin derivatives: synthesis and assessment of dopaminergic and adrenergic actions.

@article{Cannon198157Dihydroxy2aminotetralinDS,
  title={5,7-Dihydroxy-2-aminotetralin derivatives: synthesis and assessment of dopaminergic and adrenergic actions.},
  author={Joseph Gerard Cannon and Abram N. Brubaker and John Paul Long and Jan R. Flynn and T. Verimer and Peerarat Harnirattisai and Brenda Costall and Robert J. Naylor and Virinder Nohria},
  journal={Journal of medicinal chemistry},
  year={1981},
  volume={24 2},
  pages={
          149-53
        }
}
Replacement of the catechol 3,4-dihydroxylation pattern of certain adrenergic beta-phenethylamines by a resorcinol 3,5-dihydroxylation pattern has led to a greater selectivity of adrenergic agonist effects in certain molecules. This strategy has been applied to a series of dopaminergic agents derived from 2-aminotetralin, leading to a 5,7-dihydroxylation pattern. Traditional literature approaches to formation of a tetralin ring with this oxygenation pattern failed. A method was used which… 
13 Citations
Synthesis of 5-hydroxy-[6-14C]-methyl-2-di-n-propylaminotetralin
By an improved synthesis, 5-hydroxy-6-methyl-2-di-n-propylaminotetralin (DK-118), a dopamine agonist, has been obtained in only six steps and in greater than 10% overall yield. This new synthesis has
The practical synthesis of (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthylamine via optical resolution of 2-(3-methoxybenzyl)succinic acid.
TLDR
(S)-AMT was obtained from the acid (S)-2 by Hofmann rearrangement without racemization by the intramolecular Friedel-Crafts reaction followed by catalytic hydrogenation.
Structure-activity relationships of dopamine agonists.
  • J. Cannon
  • Biology
    Annual review of pharmacology and toxicology
  • 1983
TLDR
This review surveys classes of structures in which putative dopamine agonism has been reported, and cites structure-activity correlations, and a caveat must be expressed with respect to the validity of many attempted structure­ activity correlations.
Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents
Reductive amination is an important tool for synthetic organic chemists in the construction of carbon-nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an
Dopamine agonists: structure-activity relationships.
  • J. Cannon
  • Biology, Psychology
    Progress in drug research. Fortschritte der Arzneimittelforschung. Progres des recherches pharmaceutiques
  • 1985
TLDR
This review surveys classes of structures for which putative dopaminergic agonism has been reported, and cites structure-activity correlations, and some aspects of metabolism of the agents are addressed, which seem to have relevance to structure- activity considerations and to strategy of drug design.
The Status Quo and the Future
One of the great challenges in dopaminergic structure-activity relationship studies is that the elements of the dopamine molecule can be incorporated within the matrix of a variety of ring systems,
...
...