37025-58-4Relevant academic research and scientific papers
Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters
Yu, Han,Rothman, Richard B,Dersch, Christina M,Partilla, John S,Rice, Kenner C
, p. 2689 - 2692 (2000)
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 .
Chiral ytterbium complex-catalyzed direct asymmetric aldol-tishchenko reaction: Synthesis of anti-1,3-diols
Mlynarski, Jacek,Rakiel, Bartosz,Stodulski, Maciej,Suszczynska, Agata,Frelek, Jadwiga
, p. 8158 - 8167 (2007/10/03)
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.
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
Soai, Kenso,Yokoyama, Shuji,Hayasaka, Tomoiki
, p. 4264 - 4268 (2007/10/02)
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.
THE STEREOSELECTIVE REDUCTION OF α-AMINOPROPIOPHENONE DERIVATIVES WITH SODIUM BOROHYDRIDE
Kametani, Tetsuji,Kigasawa, Kazuo,Hiiragi, Mineharu,Wagatsuma, Nagatoshi,Kohagizawa, Toshitaka,Inoue, Hitoshi
, p. 775 - 778 (2007/10/02)
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.
