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J Med Chem. 1992 Oct 30;35(22):4020-6.

Synthesis and dopaminergic activity of some 3-(1,2,3,6-tetrahydro-1-pyridylalkyl)indoles. A novel conformational model to explain structure-activity relationships.

Author information

1
E. Merck Darmstadt, Preclinical Pharmaceutical Research and Central Analytical Laboratory, Germany.

Abstract

The synthesis and dopaminergic properties of a novel type of dopamine agonist is described. The number and kind of essential structural elements differ significantly from that of the rigid apomorphine-type dopamine agonists. Using standard molecular modeling techniques, a conformational model is developed proposing a U-shaped conformation which might be energetically preferred through aromatic pi-pi-interactions between both of the electron rich aromatic structural elements of this class of compounds. Superimposition of conformations of the lead compound 28 with apomorphine yields a novel model explaining the atypical structure-activity relationships found in this class of indolealkylamines.

PMID:
1359142
DOI:
10.1021/jm00100a006
[Indexed for MEDLINE]

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