- Tropane derivatives useable in particular for in vivo detection of dopamine transporters
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The present invention relates to tropane derivatives having particular use for the in vivo detection of dopamine transporters.These derivatives meet the formula in which R1 is I or Sn (R3)3, R2 is for example the methyl group, and X and Y are various substituents.The derivatives with X=CH3 and Y=H show strong specificity for the dopamine transporter compared with the serotonin transporter (74% inhibition when the transporter is previously saturated with GBR 12909).
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- Guest/host relationships in the synthesis of the novel cage-based zeolites SSZ-35, SSZ-36, and SSZ-39
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Here, we report the synthesis and structure of three high-silica molecular sieves, SSZ-35, SSZ-36, and SSZ-39, that are prepared from a library of 37 different cyclic and polycyclic quaternized amine molecules that are used as structure-directing agents (SDAs). The size and shape of the quaternized amine molecules are purposely designed in order to obtain novel zeolite structures, and the synthesis of these molecules is presented. The selectivity for the three molecular sieve phases is found to depend on both the SDA and the degree of heteroatom lattice substitution of Al3+ or B3+ in the silicate framework. Molecular modeling is utilized to probe the effects of the nonbonded SDA/zeolite-framework interaction energy on the selectivity for the observed molecular sieve phase. The Rietveld refinement of the powder X-ray data confirms the structure of the SSZ-39 zeolite to be isomorphous with the aluminophosphate molecular sieve, SAPO-18 (AEI). The structure of SSZ-36 is found to possess a range of fault probabilities between the two-dimensional channel system, end-member polymorphs, ITQ-3 and RUB-13 (International Zeolite Association Codes ITE and RTH, respectively). The SSZ-35 structure is reported to contain a one-dimensional pore system possessing stacked cages circumscribed by alternating rings of 10 and 18 tetrahedral atoms (10- and 18-membered rings).
- Wagner, Paul,Nakagawa, Yumi,Lee, Greg S.,Davis, Mark E.,Elomari, Saleh,Medrud, Ronald C.,Zones
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p. 263 - 273
(2007/10/03)
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- Tropane derivatives with selective binding to the serotonin reuptake transporters for treatment of mental illness and as intermediates in the formation of imaging diagnostic agents for depression
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Biologically active derivatives of the tropane ring system are provided which selectively bind either to the 5-HT or DA reuptake site, leading to compounds which have use for the treatment of clinical depression, attention deficit disorder, obesity and co
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- Manipulation of substituents at nitrogen in tropanes, homotropanes, and dehydro- derivatives
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Trop-6-ene (8-methyl-8-azabicyclo[3.2.1]oct-6-ene) and substituted N- benzylnortrop-6-enes are synthesised. N-Debenzylation of tropanes fails using a wide variety of non-hydrogenolytic conditions despite effective application in model piperidine derivatives; debenzylation of homotropanes is more successful, giving norhomotropane and norhomotrop-7-ene. Bridged N-benzyl compounds react more slowly than N-methyl analogues with chloroformates; the resulting quaternary intermediates are more prone than the N-methyl analogues to suffer competitive reversion to the starting amine, especially in the tropanes, consistent with slower S(N)2 attack at the benzylic carbon during decomposition; the use of an N-p-methoxybenzyl group does allow partial debenzylation to nortrop-6-ene, suggesting greater S(N)1 character in the decomposition step in this case. 'Equatorial' attack is preferred in methylation of N-benzyl-nortrop-6-ene and -homotrop-7-ene with CH3I; subsequent reductive debenzylation of the quaternary salt achieves overall replacement of N-benzyl by N-methyl in both cases. VT NMR studies show the presence of a single 'equatorial' invertomer (CI syn- to the 2C-bridge) in N- chloro-norhomotropanes and -7-enes and by analogy, in the N-alkyl compounds.
- Howarth, Nicola M.,Malpass, John R.,Smith, Craig R.
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p. 10899 - 10914
(2007/10/03)
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- N-hydroxypyridine-2-thione carbamates. V. Syntheses of alkaloid skeletons by aminium cation radical cyclizations
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The title radical precursors (PTOC carbamates) were employed as sources of a variety of 5,6-unsaturated aminium cation radicals. 5-Exo radical cyclization followed by trapping by t-BuSH or the PTOC carbamate gave a variety of aklaloid skeletons, typically in good to excellent yields, including pyrrolidines, perhydroindoles, pyrrolizidines, tropanes, 9-azabicyclo[4.2.1]nonanes, 6-azabicyclo [3.2.1]octanes. 6-Exo and 7-endo cyclizations competed in a 6,7-unsaturated system.
- Newcomb, Martin,Marquardt, Donald J.,Deeb, Thomas M.
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p. 2329 - 2344
(2007/10/02)
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- N-HYDROXYPYRIDINE-2-THIONE CARBAMATES AS AMINIUM RADICAL CATION PRECURSORS. TRANSANNULAR RADICAL CYCLIZATIONS FORMING TROPANES
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N-Methylcyclohept-4-enaminium cation radical, produced from the corresponding N-hydroxypyridine-2-thione carbamate, cyclizes to give, ultimately, tropane and substituted tropanes in high yield.
- Newcomb, Martin,Marquardt, Donald J.
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p. 129 - 132
(2007/10/02)
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- Hydroformylation of Nitrogen-Containing Cyclic Olefins via "in-situ" Rhodium-Phosphine Catalysts
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Hydroformylation of nitrogen-containing cyclic olefins (N-substituted nortropidines, N-methyl-1,2,3,6-tetrahydropyridine (THP)) with rhodium-PR3 catalysts prepared "in-situ" is reported.The nortropidines reacted rapidly when either trialkyl- or triaryl-type phosphines were used, and the regioselectivities were not significantly influenced by the nature of the phosphine.With the less basic THP the rates and selectivities were generally lower, and were influenced by the phosphine ligand and by the presence of added bases such as Et3N.
- Prokai-Tatrai, K.,Toeroes, S.,Heil, B.
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p. 231 - 236
(2007/10/02)
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- HYDROGENOLYTIC CLEAVAGE OF C=O BOND IN γ-PIPERIDONE DERIVATIVES
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The proton transfer via the hydrogen bond system of γ-aminoketones, dissolved in aqueous solution of strong acids, is postulated as the driving force for the hydrogenolytic cleavage of the C=O bond of γ-piperidone derivatives.
- Wysocka, Waleria
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