Derivatives of 4-(2-N,N-Di-n-propylaminoethyl)-5-hydroxyindole: Synthesis and Pharmacological Effects |
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Authors: | Cannon Joseph G Roufos Ioannis Ma Sheng Xing Long John Paul |
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Institution: | (1) Division of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City, Iowa, 52242;(2) Department of Pharmacology, College of Medicine, The University of Iowa, Iowa City, Iowa, 52242 |
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Abstract: | 5-Methoxy-l-methyl-4-(2-N,N-di-n-propylaminoethyl)indole (12) was synthesized from 5-hydroxyindole by a multistep synthesis. This target compound was designed as a bioisostere of p-dimethoxy catechol congeners of dopaminergic agonists derived from a variety of ring systems, in some of which p-dimethoxy-substituted systems are potent, active dopaminergic agonists. To complete the indole series, all possible combinations of N- and O-demethylated derivatives of 12 were prepared and were also evaluated pharmacologically. All members of this indole-derived series showed a low order of cardiovascular activity, which appeared to be independent of dopamine receptors. The lack of dopaminergic activity of 12 is cited as yet another example of the unpredictable effect of replacement of the catechol moiety of a dopaminergic agonist with a p-dimethoxy moiety.To whom correspondence should be addressed. |
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Keywords: | dopaminergic agonism 5-oxygenated-4-aminoethylindoles p-dimethoxy bioisosteres |
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