135-97-7Relevant articles and documents
FUSED BICYCLOHETEROCYCLE SUBSTITUTED AZABICYCLIC ALKANE DERIVATIVES
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Page/Page column 17, (2008/06/13)
The invention relates to fused bicycloheterocycle substituted azabicyclic alkane derivatives, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.
Novel 4'-Substituted and 4',4"-Disubstituted 3α-(Diphenylmethoxy)tropane Analogs as Potent and Selective Dopamine Uptake Inhibitors
Newman, Amy Hauck,Kline, Richard H.,Allen, Andrew C.,Izenwasser, Sari,George, Clifford,Katz, Jonathan L.
, p. 3933 - 3940 (2007/10/03)
A series of 4'-substituted and 4',4"-disubstituted 3α-(diphenylmethoxy)tropane analogs were prepared as novel probes for the dopamine transporter.These compounds were evaluated in radiolabeled binding assays for the dopamine, norepinephrine, and serotonin transporters.All of these compounds monophasically displaced WIN 35,428 binding in rat caudate putamen with Ki values ranging from 11.8 to 2000 nM.The most potent compound in this series was 4',4"-difluoro 3α-(diphenylmethoxy)tropane 7c with Ki=11.8 nM.All of the compounds inhibited dopamine uptake in rat caudate putamen (IC50 = 24-4456 nM) which correlated significantly (r = 0.907; p > 0.0001) with binding affinities at the dopamine transporter.None of the compounds demonstrated high-affinity binding at the norepinephrine (Ki > 4800 nM) or serotonin (Ki > 690 nM)transporters.Therefore, the most potent dopamine uptake inhibitors in this series were highly selective for the dopamine transporter.Preliminary behavioral studies of several of these analogs (7a-e) suggested that the compounds did not display a cocaine-like behavioral profile, despite their ability to inhibit dopamine uptake.The present data coupled with the 3α-(diphenylmethoxy)tropane analogs may be interacting at a different active site than cocaine on the dopamine transporter and that an additional binding domain might be exploited for the identification of potential therapeutics for the treatment of cocaine abuse.
The synthesis and separation of [3-2H]tropine and [3-2H]pseudotropine (Ψ-tropine)
Bartholomew,Smith,Darcy,Trudgill,Hopper
, p. 85 - 91 (2007/10/02)
Tropine was reduced using sodium borodeuteride to give a mixture of the epimers [3-2H]tropine and [3-2H]pseudotropine with the latter compound predominating and constituting about 70% of the mixture. Crystallisation of the product from diethyl ether gave crystals of pure [3-2H]pseudotropine and a supernatant solution containing a mixture of the epimers. Acetylation of this mixture using acetyl chloride preferentially acetylated the pseudotropine and the acetylated products were separated from the tropine by flash chromatography to leave a sample of pure [3-2H]tropine.
ALKALOIDS OF ERYTHROXYLUM HYPERICIFOLIUM LEAVES
Al-Said, Mansour S.,Evans, William C.,Grout, Raymond J.
, p. 3211 - 3216 (2007/10/02)
Fifteen alkaloids were characterized from the leaves of Erythroxylum hypericifolium; the majority are esters of cinnamic acid and benzoic acids. 3α-cinnamoyloxytropan-6-β-ol is the main base.New alkaloids reported are 3β-cinnamoyloxytropane, 3α,6β-dicinnamoyloxytropane,3-cinnamoyloxynortropan-6-ol, 6β-acetoxy-3α-cinnamoyloxytropane and, tentatively, 6-phenylacetoxytropan-3-ol.Two mixed cinnamate dimers were also found.Some syntheses are reported and the chemotaxonomic implications of the results are discussed. Key Word Index Erythroxylum hypericifolium; Erythroxylaceae; leaves; tropane alkaloids; cinnamate dimers; tropane alkaloid synthesis; chemotaxonomy.
Purification and Characterization of Pseudotropine Forming Tropinone Reductase from Hyoscyamus niger Root Cultures
Draeger, Birgit,Hashimoto, Takashi,Yamada, Yasuyuki
, p. 2663 - 2668 (2007/10/02)
A pseudotropine-forming tropinone reductase was extracted from root cultures of Hyoscyamus niger that produce the tropane alkaloids hyosciamine and scopolamine.The enzyme stereospecifically reduces tropinone to pseudotropine, oxidizing NADPH.It has an approximate molecular weight 84,000 and a pH optimum between 5.8 and 6.25.The Km value for tropinone is 35.1 μmol/l and for NADPH 21.1 μmol/l.Substrate specificity was tested for NADPH and several and several tropinone analogues.
STEREOCONTROLLED SYNTHESIS OF TROPANOL DERIVATIVES VIA PALLADIUM-CATALYZED REACTIONS
Baeckvall, J. E.,Renko, Z. D.,Bystroem, S. E.
, p. 4199 - 4202 (2007/10/02)
A general method for the transformation of 1,3-cycloheptadienes to tropane alkaloid derivatives was developed.The procedure was applied to the stereocontrolled synthesis of the exo- and endo-tropanol derivatives 1 and 2.The approach is based on a dual stereocontrol in the 1,4-functionalization of conjugated dienes.
