Derivatives of 5-hydroxy-6-methyl-2-aminotetralin.

  title={Derivatives of 5-hydroxy-6-methyl-2-aminotetralin.},
  author={Joseph Gerard Cannon and D. L. Koble and John Paul Long and T. Verimer},
  journal={Journal of medicinal chemistry},
  volume={23 7},
The title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation. A sequence leading to a key synthetic intermediate, 5-methoxy-6-methyl-2-tetralone, has been developed. In animal test models for dopamine-like effects, the title compounds demonstrated qualitative and quantitative differences from the isomeric 5-methyl-6-hydroxy-2-aminotetralins and from 5,6-dihydroxy-2-aminotetralins. Two of… 
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 2-aminotetralin system as a structural base for new dopamine- and melatonin-receptor agents
The research described in this thesis is divided into two parts; part I deals with the development of a novel 2-aminotetralin as a mixed dopamine Dl/D2-receptor agonist, and part I1 concerns thedevelopment of 2-amidOTetralins as nonindolic melatonin-recept agents.
Opioid Receptor Effects Of Two Aminotetralin Derivatives In Guinea Pig Ileum Longitudinal Muscle And Mouse Vas Deferens Preparations
It was demonstrated that compound J inhibited contractions in a concentration-dependent manner as an opioid agonist and its effects were antagonized by naloxone in both preparations, suggesting a preference for mu receptors.
Intramolecular capture of pummerer rearrangement intermediates. I. Synthesis of pyrrolo[2,1‐c][1,4]benzothiazines
Treatment of 1-(2-alkylsulfinylphenyl)pyrroles with trifluoroacetic acid in refluxing toluene gives 4-substituted pyrrolo[2,1-c][1,4]benzothiazines in good yield when the alkyl group bears an
Structure-activity relationships of dopamine agonists.
  • J. Cannon
  • Biology
    Annual review of pharmacology and toxicology
  • 1983
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.
In‐vitro and in‐vivo metabolism of the presynaptic dopamine agonist 3‐PPP to a catecholic analogue in rats *
The dopamine agonist 3‐PPP and its enantiomers are hydroxylated in‐vitro by rat liver microsomes to the catecholamine 3‐(3,4‐dihydroxyphenyl)‐ N‐n‐propylpiperidine (4‐OH‐3‐PPP) with Km and Vmax
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
Reductions by Metal Alkoxyaluminum Hydrides. Part II. Carboxylic Acids and Derivatives, Nitrogen Compounds, and Sulfur Compounds
In continuation of the previous review on reductions by metal alkoxyaluminum hydrides, this chapter is devoted to reductions of carboxylic acids and their derivatives, open-chain and heterocyclic