• DOI:10.1021/JM00160A036
• Corpus ID: 1196203

Assessment of a potential dopaminergic prodrug moiety in several ring systems.

@article{Cannon1986AssessmentOA,
  title={Assessment of a potential dopaminergic prodrug moiety in several ring systems.},
  author={Joseph Gerard Cannon and David C. Furlano and Russell G. Dushin and Y A Chang and Samuel R. Baird and L N Soliman and Jan R. Flynn and John Paul Long and Raj Bhatnagar},
  journal={Journal of medicinal chemistry},
  year={1986},
  volume={29 10},
  pages={
          2016-20
        }
}

• J. Cannon, D. Furlano, +6 authors R. Bhatnagar
• Published 1 October 1986
• Chemistry
• Journal of medicinal chemistry

The ortho hydroxy/methyl, hydroxy/hydroxymethyl, hydroxy/formyl, and hydroxy/carboxy substitution patterns, some of which confer dopaminergic agonist effects upon 2-aminotetralin ring systems, have been incorporated into beta-phenethylamine, 2-aminoindan, and trans-octahydrobenzo[f]quinoline rings. Certain of the 2-aminoindan derivatives displayed pharmacologic properties consistent with their being dopaminergic agonists. The beta-phenethylamine derivative did not show any significant dopamine-like activity. The 7-hydroxy-8-methyloctahydrobenzo[f]quinoline derivative 4a was a moderately potent, short-acting DA2 receptor antagonist. All of the carboxylic acid derivatives were inert. Of the ortho hydroxy/methyl derivatives, only the 5-hydroxy-6-methyl-2-aminotetralin derivative displayed pharmacological properties consistent with its being a dopaminergic prodrug. It is concluded that 5-hydroxy-6-methyl-2-(di-n-propylamino)tetralin (1a) is structurally unique for a dopaminergic drug.