- Diborane as a reducing agent IX [1]: Reduction of a tris(trifluoroacetyl)enaminospiroindoline
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Reduction of the title compound (2) with diborane furnishes 1-trifluoroethyl-3-(2′-(trifluoroethylamino)ethyl)-3-vinylindoline (4), 1-hydroxy-trifluoroethyl-3-(2′-(trifluoroethylamino)-ethyl)indole (5), and 1-methyl-2-trifluoroethyl-1,2,3,4-tetrahydro-β-carboline (6). However, treatment of 2 with lithium aluminum hydride, H2/Pd on charcoal, and sodium borohydride affords hydroxyspiroindolenine 8, hydroxy-bis(trifluoroacetyl)enaminospiroindoline 9, and N-ethyltryptamine 7, respectively. The results are discussed and the mechanisms of the reactions leading to 4-8 are presented.
- Biswas,Mallik,Halder
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- Alpha-ethyltryptamines as dual dopamine-serotonin releasers
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The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2Areceptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2Areceptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential.
- Blough, Bruce E.,Landavazo, Antonio,Partilla, John S.,Decker, Ann M.,Page, Kevin M.,Baumann, Michael H.,Rothman, Richard B.
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p. 4754 - 4758
(2015/01/09)
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