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Cannon, J.G. et al.

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

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 involved cyclization of 3,5-dimethoxybenzylsuccinic acid derivatives with pyridinium poly(HF) and subsequent modification of the tetralin ring. The resorcinol-derived 2-aminotetralins were less potent and less active dopaminergic agents than their catechol-derived isomers (5,6-dihydroxy and/or 6,7-dihydroxy). Certain of the subject compounds demonstrated alpha- and beta 1-adrenoceptor activating properties.[1]

References

5,7-Dihydroxy-2-aminotetralin derivatives: synthesis and assessment of dopaminergic and adrenergic actions. Cannon, J.G., Brubaker, A.N., Long, J.P., Flynn, J.R., Verimer, T., Harnirattisai, P., Costall, B., Naylor, R.J., Nohria, V. J. Med. Chem. (1981) [Pubmed]

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