406945-51-5Relevant articles and documents
Dual DAT/σ1 receptor ligands based on 3-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-1-phenylpropan-1-ol
Cao, Jianjing,Kopajtic, Theresa,Katz, Jonathan L.,Newman, Amy Hauck
supporting information; experimental part, p. 5238 - 5241 (2009/05/12)
Ester analogs of (±)3-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-1-phenylpropan-1-ol were synthesized and evaluated for binding at DAT, SERT, NET, and σ1 receptors, and compared to GBR 12909 and several known σ1 receptor ligands. Most of these compounds demonstrated high affinity (Ki = 4.3-51 nM) and selectivity for the DAT among the monoamine transporters. S- and R-1-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-3-phenylpropan-2-ol were also prepared wherein modest enantioselectivity was demonstrated at the DAT. However, no enantioselectivity at σ1 receptors was observed and most of the ester analogs of the more active S-enantiomer showed comparable binding affinities at both DAT and σ1 receptors with a maximal 16-fold DAT/σ1 selectivity.
Stereo-complementary two-step cascades using a two-enzyme system leading to enantiopure epoxides
Seisser, Birgit,Lavandera, Ivan,Faber, Kurt,Spelberg, Jeffrey H. Lutje,Kroutil, Wolfgang
, p. 1399 - 1404 (2008/03/28)
A novel one-pot, two-step, two-enzyme cascade is described. Pro-chiral α-chloro ketones are stereoselectively reduced to the corresponding halohydrins as an intermediate by a biocatalytic hydrogen transfer process. The intermediate is transformed to the corresponding epoxide by a non-enantioselective halohydrin dehalogenase. Thus, by combining a Prelog- or anti-Prelog alcohol dehydrogenase with a non-selective halohydrin dehalogenase, enantiopure (R)- as well as (S)-epoxides were obtained.
Non-racemic halohydrins via biocatalytic hydrogen-transfer reduction of halo-ketones and one-pot cascade reaction to enantiopure epoxides
Poessl, Tina M.,Kosjek, Birgit,Ellmer, Ursula,Gruber, Christian C.,Edegger, Klaus,Faber, Kurt,Hildebrandt, Petra,Bornscheuer, Uwe T.,Kroutil, Wolfgang
, p. 1827 - 1834 (2007/10/03)
Biocatalytic hydrogen-transfer reduction of α-chloro-ketones furnished non-racemic chlorohydrins by employing either Rhodococcus ruber as lyophilized cell catalyst or an alcohol dehydrogenase preparation from Pseudomonas fluorescens DSM 50106 (PF-ADH). Fo
Chemoenzymatic dynamic kinetic resolution of β-halo alcohols. An efficient route to chiral epoxides
Pamies, Oscar,Baeckvall, Jan-E.
, p. 9006 - 9010 (2007/10/03)
Enzymatic resolution of β-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when β-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation of the enzyme. The synthetic utility of this procedure has been illustrated by the practical synthesis of different chiral epoxides.
Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: Chiral hydroxyl-containing derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy) ethyl]-4-(3-ph
Hsin, Ling-Wei,Dersch, Christina M.,Baumann, Michael H.,Stafford, David,Glowa, John R.,Rothman, Richard B.,Jacobson, Arthur E.,Rice, Kenner C.
, p. 1321 - 1329 (2007/10/03)
In our search for long-acting agents for the treatment of cocaine abuse, a series of optically pure hydroxylated derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (1) and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)pip
Pseudomonas Lipases as Catalysts in Organic Synthesis: Specificity of Lipoprotein Lipase
Kim, Mahn-Joo,Cho, Hangjin
, p. 1411 - 1413 (2007/10/02)
Described are the structural features of the substrates accepted by lipoprotein lipase from Pseudomonas aeruginosa which can serve as the rules for interpreting and predicting the specificity of this enzyme.