Synthesis and dopaminergic activity of 3-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans: characterization of an auxiliary binding region in the D1 receptor.

@article{Deninno1991SynthesisAD,
  title={Synthesis and dopaminergic activity of 3-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans: characterization of an auxiliary binding region in the D1 receptor.},
  author={Michael Paul Deninno and Robert W Schoenleber and Richard J. Perner and Lawrence E. Lijewski and Karen E. Asin and Donald R. Britton and Robert G. Mackenzie and John W. Kebabian},
  journal={Journal of medicinal chemistry},
  year={1991},
  volume={34 8},
  pages={
          2561-9
        }
}
The synthesis and dopaminergic activity of a series of C3 and nitrogen-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans (isochromans) is described. The synthesis of the compounds was stereospecific for the 1,3 cis isomer, and the enantioselective synthesis of both enantiomers of one of the analogues (20) was achieved. It was determined that all of the dopaminergic activity resides in the [1R,3S] isomer. Generally, substitution at the C3 position provided compounds with… CONTINUE READING

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