- Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters
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Three metabolites of diethylpropion (1), (±)-2-ethylamino-1-phenyl-propan-1-one (2), (1R,2S)-(-)-N,N-diethylnorephedrine (3a) and (1S,2R)-(-)-N,N-diethylnorephedrine (3b) were synthesized. Their uptake and release effects with biogenic amine transporters were evaluated. A major finding of this study is that the in vivo activity of diethylpropion on biogenic amine transporters is most likely due to metabolite 2 as diethylpropion (1) and the metabolites 3a and 3b showed little or no effect in the assays studied. These studies also revealed that 2 acted as a substrate at the norepinephrine (IC50=99nM) and serotonin transporters (IC50=2118nM) and an uptake inhibitor at the dopamine transporter (IC50=1014nM). The potent action of 2 at the NE transporter supports the hypothesis that amphetamine-type subjective effects may be mediated in part by brain norepinephrine. Copyright (C) 2000 .
- Yu, Han,Rothman, Richard B,Dersch, Christina M,Partilla, John S,Rice, Kenner C
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- Chiral ytterbium complex-catalyzed direct asymmetric aldol-tishchenko reaction: Synthesis of anti-1,3-diols
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The asymmetric aldol-Tishchenko reaction of aromatic aldehydes with aliphatic and aromatic ketones has been developed as an efficient strategy for the synthesis of anti-1,3-diols in good yield with high diastereo-control and good levels of enantiose-lectivity. This domino-type reaction is catalyzed by a chiral ytterbium complex that promotes both the aldol reaction through enolization of the carbon yl compound and the Evans-Tishchenko reduction of the aldol intermediate. The stereochemistry of the resulting diols is also investigated and finally proved by using CD techniques.
- Mlynarski, Jacek,Rakiel, Bartosz,Stodulski, Maciej,Suszczynska, Agata,Frelek, Jadwiga
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p. 8158 - 8167
(2007/10/03)
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- Chiral N,N-Dialkylnorephedrines as Catalysts of the Highly Enantioselective Addition of Dialkylzincs to Aliphatic and Aromatic Aldehydes. The Asymmetric Synthesis of Secondary Aliphatic and Aromatic Alcohols of High Optical Purity
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The chiral N,N-dialkylnorephedrine-catalyzed addition of dialkylzincs to aliphatic and aromatic aldehydes afforded secondary alcohols of high optical purity (to > 95percent ee).Among the N,N-di(primary alkyl)norephedrines, N,N-di-n-butylnorephedrine (DBNE, 3d) was found to be the most effective catalyst. 1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (3i) and N,N-diallylnorephedrine (3j) were also highly effective catalysts.The method described provides optically active secondary aliphatic alcohols of high optical purity which cannot be prepared by conventional methods.
- Soai, Kenso,Yokoyama, Shuji,Hayasaka, Tomoiki
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p. 4264 - 4268
(2007/10/02)
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- THE STEREOSELECTIVE REDUCTION OF α-AMINOPROPIOPHENONE DERIVATIVES WITH SODIUM BOROHYDRIDE
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The ratio of erythro and threo products from the sodium borohydride reduction of the hydrochlorides, and other acid salts, of α-aminopropiophenone derivatives was determined.It was found that this procedure resulted in stereoselective formation of erythro-2-amino-1-phenylpropanols in contrast to sodium borohydride reduction of the corresponding free bases.The method was successfully applied to the synthesis of dl-erythro-2-(4-benzylpiperidino)-1-(4-hydroxyphenyl)propanol which has been used as a vasodilator.
- Kametani, Tetsuji,Kigasawa, Kazuo,Hiiragi, Mineharu,Wagatsuma, Nagatoshi,Kohagizawa, Toshitaka,Inoue, Hitoshi
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p. 775 - 778
(2007/10/02)
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